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Hyoscine

PubChem CID
3000322
Structure
Hyoscine_small.png
Hyoscine_3D_Structure.png
Molecular Formula
Synonyms
  • scopolamine
  • Hyoscine
  • 51-34-3
  • (-)-Hyoscine
  • Scopine (-)-tropate
Molecular Weight
303.35 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-29
  • Modify:
    2025-01-18
Description
Scopolamine hydrobromide appears as colorless crystals or white powder or solid. Has no odor. pH (of 5% solution): 4-5.5. Slightly efflorescent in dry air. Bitter, acrid taste. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Scopolamine is a tropane alkaloid that is the (S)-tropic acid ester of 6beta,7beta-epoxy-1alphaH,5alphaH-tropan-3alpha-ol. It has a role as a muscarinic antagonist, an antiemetic, an adjuvant, a mydriatic agent, an antispasmodic drug, an anaesthesia adjuvant, an antidepressant and a metabolite. It is a propanoate ester, an epoxide, a tertiary amino compound and a tropane alkaloid. It is functionally related to a (S)-tropic acid. It is a conjugate base of a scopolamine(1+).
Scopolamine is a tropane alkaloid isolated from members of the Solanaceae family of plants, similar to [atropine] and [hyoscyamine], all of which structurally mimic the natural neurotransmitter [acetylcholine]. Scopolamine was first synthesized in 1959, but to date, synthesis remains less efficient than extracting scopolamine from plants. As an acetylcholine analogue, scopolamine can antagonize muscarinic acetylcholine receptors (mAChRs) in the central nervous system and throughout the body, inducing several therapeutic and adverse effects related to alteration of parasympathetic nervous system and cholinergic signalling. Due to its dose-dependent adverse effects, scopolamine was the first drug to be offered commercially as a transdermal delivery system, Scopoderm TTS®, in 1981. As a result of its anticholinergic effects, scopolamine is being investigated for diverse therapeutic applications; currently, it is approved for the prevention of nausea and vomiting associated with motion sickness and surgical procedures. Scopolamine was first approved by the FDA on December 31, 1979, and is currently available as both oral tablets and a transdermal delivery system.
See also: Scopolamine (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Hyoscine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1R,2R,4S,5S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11?,12-,13-,14+,15-,16+/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

STECJAGHUSJQJN-USLFZFAMSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CN1[C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)[C@H](CO)C4=CC=CC=C4
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C17H21NO4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

114-49-8
51-34-3

2.3.2 Deprecated CAS

14797-94-5, 226562-00-1, 28901-63-5, 58670-87-4, 65319-33-7, 97991-84-9
226562-00-1, 28901-63-5, 58670-87-4, 65319-33-7, 97991-84-9

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 Metabolomics Workbench ID

2.3.10 NCI Thesaurus Code

2.3.11 Pharos Ligand ID

2.3.12 RXCUI

2.3.13 Wikidata

2.3.14 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Boro Scopol
  • Boro-Scopol
  • Hyoscine
  • Isopto Hyoscine
  • Kwells
  • Scoburen
  • Scopace
  • Scopoderm TTS
  • Scopolamine
  • Scopolamine Cooper
  • Scopolamine Hydrobromide
  • Transderm Scop
  • Transderm V
  • Transderm-V
  • Travacalm HO
  • Vorigeno

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
303.35 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
0.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
303.14705815 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
303.14705815 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
62.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
22
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
418
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
5
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Scopolamine hydrobromide appears as colorless crystals or white powder or solid. Has no odor. pH (of 5% solution): 4-5.5. Slightly efflorescent in dry air. Bitter, acrid taste. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

3.2.2 Color / Form

Viscous liquid
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1450

3.2.3 Melting Point

387 °F (decomposes) (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
59 °C
ChemSpider
59 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1450
White powder; mp: about 80 °C; specific rotation: -14 deg at 20 °C/D (water) /N-oxide/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1450

3.2.4 Solubility

greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
1.0X10+5 mg/L
Yalkowsky, S.H. & He, Y. (2003)
Crystals from acetone; very sol in water and alcohol; pH of 0.05 molar soln: 5.85 /Scopolamine hydrochloride/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1450
Sol in 9.5 parts water at 15 °C; freely sol in alcohol, ether, chloroform, acetone; sparingly sol in benzene, petroleum ether
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1450
Very soluble in hot water
Lide, D.R. CRC Handbook of Chemistry and Physics 88TH Edition 2007-2008. CRC Press, Taylor & Francis, Boca Raton, FL 2007, p. 3-458
In water, 1.0X10+5 mg/L, temp not specified
Yalkowsky, S.H., He, Yan., Handbook of Aqueous Solubility Data: An Extensive Compilation of Aqueous Solubility Data for Organic Compounds Extracted from the AQUASOL dATAbASE. CRC Press LLC, Boca Raton, FL. 2003., p. 1080

3.2.5 LogP

0.98
Sangster (1994)
log Kow = 0.98
Sangster J; LOGKOW Data Base. Montreal, Quebec, Canada: Sangster Res Lab (1994)

3.2.6 Stability / Shelf Life

The commercially available transdermal system of scopolamine should be stored at controlled room temperature between 20 and 25 °C. Scopolamine hydrobromide should be stored in tight, light-resistant containers. Scopolamine hydrobromide injections should be stored in light-resistant, single-dose or multiple-dose containers, preferably of USP Type I glass, at 15 to 30 °C; freezing of the injections should be avoided. Commercially available scopolamine hydrobromide soluble tablets should be stored at controlled room temperature (15 to 30 °C).
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1323
SENSITIVE TO LIGHT & AIR. /HYDROBROMIDE TRIHYDRATE/
Sunshine, I. (ed.). CRC Handbook of Analytical Toxicology. Cleveland: The Chemical Rubber Co., 1969., p. 107

3.2.7 Optical Rotation

Orthorhombic sphenoidal crystals from water, slightly efflorescent in dry air. MP 195 °C (after drying at 105 °For 3 hrs). Specific optical rotation: -24 to -26 deg at 25 °C/D ( c = 5, calculated on anhydrous basis). UV max (emethanol): 246, 252, 258, 264 nm (A (1%, 1 cm): 3.5, 4.0, 4,5, 3.0). pH of 0.5M solution 5.85. One gram dissolves in 1.5 ML water, 20 mL alcohol. Slightly soluble in chloroform. Practically insoluble in ether. /Hydrobromide trihydrate/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1460
Specific optical rotation: -28 deg at 20 °C/D ( c = 2.7)
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1450

3.2.8 Ionization Efficiency

Ionization mode
Positive
logIE
3.61
pH
2.7
Instrument
Agilent XCT
Ion source
Electrospray ionization
Additive
formic acid (5.3nM)
Organic modifier
MeCN (80%)

3.2.9 Caco2 Permeability

-4.93
ADME Research, USCD

3.2.10 Dissociation Constants

pKa
7.75
Sangster, J (1994)
pKa = 7.75
Sangster J; LOGKOW Data Base. Montreal, Quebec, Canada: Sangster Res Lab (1994)

3.2.11 Collision Cross Section

171.1 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
170.5 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]

3.2.12 Other Experimental Properties

Crystals. Freely soluble in water, dilute alcohol; slightly soluble in absolute alcohol /Methyl nitrate/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1450
Dihydrate: chisel-shaped prisms from ethanol+water, mp 38-40 °C. Monohydrate: efflorescent crystals, mp 55-57 °C. Anhydrous: long prisms, mp 82-82 °C. Very slightly soluble in water; soluble in alcohol, chlorform, ether, oils /DL-form/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1450
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 842
COLORLESS OR WHITE CRYSTALS OR WHITE GRANULAR POWDER /SCOPOLAMINE HYDROBROMIDE NF/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 842

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
S58 | PSYCHOCANNAB | Synthetic Cannabinoids and Psychoactive Compounds | DOI:10.5281/zenodo.3247723
3.3.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Adjuvants, Anesthesia; Mydriatics; Muscarinic Antagonists; Parasympatholytics
Human drug -> Prescription; Active ingredient (SCOPOLAMINE)
Human drug -> Prescription
Medicines for other common symptoms in palliative care
3.3.1.2 Animal Drugs
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

MS Category
Experimental
MS Type
GC-MS
Instrument Type
GC-MS
Top 5 Peaks

94.0 1

138.0 0.76

108.0 0.34

154.0 0.27

97.0 0.24

Thumbnail
Thumbnail

4.1.2 LC-MS

1 of 9
View All
Authors
Cuthbertson DJ, Johnson SR, Lange BM, Institute of Biological Chemistry, Washington State University
Instrument
Agilent 1200 RRLC; Agilent 6520 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS
Ionization Mode
POSITIVE
Column Name
Agilent C8 Cartridge Column 2.1X30mm 3.5 micron (guard); Agilent SB-Aq 2.1x50mm 1.8 micron (analytical)
Retention Time
2.078
Top 5 Peaks

304.15434 999

326.136282 59

Thumbnail
Thumbnail
License
CC BY-SA
2 of 9
View All
Authors
Cuthbertson DJ, Johnson SR, Lange BM, Institute of Biological Chemistry, Washington State University
Instrument
Agilent 1200 RRLC; Agilent 6520 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS
Ionization Mode
NEGATIVE
Column Name
Agilent C8 Cartridge Column 2.1X30mm 3.5 micron (guard); Agilent SB-Aq 2.1x50mm 1.8 micron (analytical)
Retention Time
2.23
Top 5 Peaks
302.139788 999
Thumbnail
Thumbnail
License
CC BY-SA

4.1.3 Other MS

1 of 4
View All
Other MS
MASS: 79741 (NIST/EPA/MSDC Mass Spectral database, 1990 version); 2275 (National Bureau of Standards)
2 of 4
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
304.1543346
Ionization Mode
positive
Retention Time
2.343092092
Top 5 Peaks

138.091118 0.55

156.101791 0.22

121.064451 0.13

110.094002 0.05

98.059409 0.03

Thumbnail
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4.2 Other Spectra

Intense mass spectral peaks: 94 m/z, 138 m/z, 154 m/z, 285 m/z, 303 m/z
Pfleger, K., H. Maurer and A. Weber. Mass Spectral and GC Data of Drugs, Poisons and their Metabolites. Parts I and II. Mass Spectra Indexes. Weinheim, Federal Republic of Germany. 1985., p. 532

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Scopolamine is indicated in adult patients for the prevention of nausea and vomiting associated with motion sickness and for the prevention of postoperative nausea and vomiting (PONV) associated with anesthesia or opiate analgesia.

7.2 Drug Classes

Breast Feeding; Lactation; Milk, Human; Adjuvants, Anesthesia; Mydriatics; Muscarinic Antagonists; Parasympatholytics

7.3 WHO Essential Medicines

Drug
Drug Classes
Medicines for other common symptoms in palliative care
Formulation
(1) Local - Topical - Transdermal patch: 1 mg per 72 hours transdermal patch; (2) Parenteral - General injections - unspecified: 400 µg per mL injection; 600 µg per mL injection
Indication
Palliative care

7.4 FDA Approved Drugs

7.5 FDA Orange Book

7.6 FDA National Drug Code Directory

7.7 Drug Labels

Active ingredient and drug
Drug and label
Active ingredient and drug

7.8 Clinical Trials

7.8.1 ClinicalTrials.gov

7.8.2 EU Clinical Trials Register

7.8.3 NIPH Clinical Trials Search of Japan

7.9 Therapeutic Uses

Adjuvants, Anesthesia; Antiemetics; Muscarinic Antagonists; Mydriatics; Parasympatholytics
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
Although transdermal scopolamine has been shown to decrease basal acid output and inhibit betazole-, pentagastrin-, and peptone-stimulated gastric acid secretion in healthy individuals, it has not been determined whether transdermal scopolamine is effective in the adjunctive treatment of peptic ulcer disease. /Use is not currently included in the labeling approved by the US FDA/
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1321
Transdermal scopolamine has shown minimal antiemetic activity against chemotherapy-induced vomiting. /Use is not currently included in the labeling approved by the US FDA/
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1321
Scopolamine hydrobromide is used as a mydriatic and cycloplegic, especially when the patient is sensitive to atropine or when less prolonged cycloplegia is required. The effects of the drug appear more rapidly and have a shorter duration of action than those of atropine. Scopolamine hydrobromide is also used in the management of acute inflammatory conditions (i.e., iridocyclitis) of the iris and uveal tract. /Scopolamine hydrobromide/
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2912
For more Therapeutic Uses (Complete) data for SCOPOLAMINE (10 total), please visit the HSDB record page.

7.10 Drug Warnings

The use of scopolamine to produce tranquilization and amnesia in a variety of circumstances, including labor, is declining and of questionable value. Given alone in the presence of pain or severe anxiety, scopolamine may induce outbursts of uncontrolled behavior.
Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 11th ed. New York, NY: McGraw-Hill, 2006., p. 197
Scopolamine in therapeutic doses normally causes CNS depression manifested as drowsiness, amnesia, fatigue, and dreamless sleep, with a reduction in rapid eye movement (REM) sleep. It also causes euphoria and is therefore subject to some abuse. The depressant and amnesic effects formerly were sought when scopolamine was used as an adjunct to anesthetic agents or for preanesthetic medication. However, in the presence of severe pain, the same doses of scopolamine can occasionally cause excitement, restlessness, hallucinations, or delirium. These excitatory effects resemble those of toxic doses of atropine.
Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 11th ed. New York, NY: McGraw-Hill, 2006., p. 191-2
Scopolamine-induced inhibition of salivation occurs within 30 minutes or within 30 minutes to 1 hour and peaks within 1 or 1-2 hours after IM or oral administration, respectively; inhibition of salivation persists for up to 4-6 hours. Following IV administration of a 0.6-mg dose in one study, amnesia occurred within 10 minutes, peaked between 50-80 minutes, and persisted for at least 120 minutes after administration. Following IM administration of a 0.2-mg dose of scopolamine in one study, antiemetic effect occurred within 15-30 minutes and persisted for about 4 hours. Following IM administration of a 0.1- or 0.2-mg dose in another study, mydriasis persisted for up to 8 hours. The transdermal system is designed to provide an antiemetic effect with an onset of about 4 hours and with a duration of up to 72 hours after application.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1323
Small doses of ... scopolamine inhibit the activity of sweat glands innervated by sympathetic cholinergic fibers, and the skin becomes hot and dry. Sweating may be depressed enough to raise the body temperature, but only notably so after large doses or at high environmental temperatures.
Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 11th ed. New York, NY: McGraw-Hill, 2006., p. 194
For more Drug Warnings (Complete) data for SCOPOLAMINE (21 total), please visit the HSDB record page.

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Scopolamine is an anticholinergic belladonna alkaloid that, through competitive inhibition of muscarinic receptors, affects parasympathetic nervous system function and acts on smooth muscles that respond to acetylcholine but lack cholinergic innervation. Formulated as a patch, scopolamine is released continuously over three days and remains detectable in urine over a period of 108 hours. Scopolamine is contraindicated in angle-closure glaucoma and should be used with caution in patients with open-angle glaucoma due to scopolamine's ability to increase intraocular pressure. Also, scopolamine exhibits several neuropsychiatric effects: exacerbated psychosis, seizures, seizure-like, and other psychiatric reactions, and cognitive impairment; scopolamine may impair the ability of patients to operate machinery or motor vehicles, play underwater sports, or perform any other potentially hazardous activity. Women with severe preeclampsia should avoid scopolamine. Patients with gastrointestinal or urinary disorders should be monitored frequently for impairments, and scopolamine should be discontinued if these develop. Scopolamine can cause blurred vision if applied directly to the eye, and the transdermal patch should be removed before an MRI procedure to avoid skin burns. Due to its gastrointestinal effects, scopolamine can interfere with gastric secretion testing and should be discontinued at least 10 days before performing the test. Finally, scopolamine may induce dependence and resulting withdrawal symptoms, such as nausea, dizziness, vomiting, gastrointestinal disturbances, sweating, headaches, bradycardia, hypotension, and various neuropsychiatric manifestations following treatment discontinuation; severe symptoms may require medical attention.

8.2 MeSH Pharmacological Classification

Adjuvants, Anesthesia
Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage. (See all compounds classified as Adjuvants, Anesthesia.)
Antiemetics
Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)
Cholinergic Antagonists
Drugs that bind to but do not activate CHOLINERGIC RECEPTORS, thereby blocking the actions of ACETYLCHOLINE or cholinergic agonists. (See all compounds classified as Cholinergic Antagonists.)
Muscarinic Antagonists
Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)
Mydriatics
Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)

8.3 FDA Pharmacological Classification

1 of 2
FDA UNII
DL48G20X8X
Active Moiety
SCOPOLAMINE
Pharmacological Classes
Established Pharmacologic Class [EPC] - Anticholinergic
Pharmacological Classes
Mechanisms of Action [MoA] - Cholinergic Antagonists
FDA Pharmacology Summary
Scopolamine is an Anticholinergic. The mechanism of action of scopolamine is as a Cholinergic Antagonist.
2 of 2
Non-Proprietary Name
SCOPOLAMINE
Pharmacological Classes
Cholinergic Antagonists [MoA]; Anticholinergic [EPC]

8.4 ATC Code

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

S - Sensory organs

S01 - Ophthalmologicals

S01F - Mydriatics and cycloplegics

S01FA - Anticholinergics

S01FA02 - Scopolamine

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CM - Other hypnotics and sedatives

N05CM05 - Scopolamine

A - Alimentary tract and metabolism

A04 - Antiemetics and antinauseants

A04A - Antiemetics and antinauseants

A04AD - Other antiemetics

A04AD01 - Scopolamine

8.5 Absorption, Distribution and Excretion

Absorption
The pharmacokinetics of scopolamine differ substantially between different dosage routes. Oral administration of 0.5 mg scopolamine in healthy volunteers produced a Cmax of 0.54 ± 0.1 ng/mL, a tmax of 23.5 ± 8.2 min, and an AUC of 50.8 ± 1.76 ng\*min/mL; the absolute bioavailability is low at 13 ± 1%, presumably because of first-pass metabolism. By comparison, IV infusion of 0.5 mg scopolamine over 15 minutes resulted in a Cmax of 5.00 ± 0.43 ng/mL, a tmax of 5.0 min, and an AUC of 369.4 ± 2.2 ng\*min/mL. Other dose forms have also been tested. Subcutaneous administration of 0.4 mg scopolamine resulted in a Cmax of 3.27 ng/mL, a tmax of 14.6 min, and an AUC of 158.2 ng\*min/mL. Intramuscular administration of 0.5 scopolamine resulted in a Cmax of 0.96 ± 0.17 ng/mL, a tmax of 18.5 ± 4.7 min, and an AUC of 81.3 ± 11.2 ng\*min/mL. Absorption following intranasal administration was found to be rapid, whereby 0.4 mg of scopolamine resulted in a Cmax of 1.68 ± 0.23 ng/mL, a tmax of 2.2 ± 3 min, and an AUC of 167 ± 20 ng\*min/mL; intranasal scopolamine also had a higher bioavailability than that of oral scopolamine at 83 ± 10%. Due to dose-dependent adverse effects, the transdermal patch was developed to obtain therapeutic plasma concentrations over a longer period of time. Following patch application, scopolamine becomes detectable within four hours and reaches a peak concentration (tmax) within 24 hours. The average plasma concentration is 87 pg/mL, and the total levels of free and conjugated scopolamine reach 354 pg/mL.
Route of Elimination
Following oral administration, approximately 2.6% of unchanged scopolamine is recovered in urine. Compared to this, using the transdermal patch system, less than 10% of the total dose, both as unchanged scopolamine and metabolites, is recovered in urine over 108 hours. Less than 5% of the total dose is recovered unchanged.
Volume of Distribution
The volume of distribution of scopolamine is not well characterized. IV infusion of 0.5 mg scopolamine over 15 minutes resulted in a volume of distribution of 141.3 ± 1.6 L.
Clearance
IV infusion of 0.5 mg scopolamine resulted in a clearance of 81.2 ± 1.55 L/h, while subcutaneous administration resulted in a lower clearance of 0.14-0.17 L/h.
Scopolamine hydrobromide is rapidly absorbed following IM or subcutaneous injection. The drug is well absorbed from the GI tract, principally from the upper small intestine. Scopolamine also is well absorbed percutaneously. Following topical application behind the ear of a transdermal system, scopolamine is detected in plasma within 4 hours, with peak concentrations occurring within an average of 24 hours. In one study in healthy individuals, mean free and total (free plus conjugated) plasma scopolamine concentrations of 87 and 354 pg/mL, respectively, have been reported within 24 hours following topical application of a single transdermal scopolamine system that delivered approximately 1 mg/72 hours. /Scopolamine hydrobromide/
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1323
Following oral administration of a 0.906-mg dose of scopolamine in one individual, a peak concentration of about 2 ng/mL was reached within 1 hour. Although the commercially available transdermal system contains 1.5 mg of scopolamine, the membrane-controlled diffusion system is designed to deliver approximately 1 mg of the drug to systemic circulation at an approximately constant rate over a 72-hour period. An initial priming dose of 0.14 mg of scopolamine is released from the adhesive layer of the system at a controlled, asymptotically declining rate over 6 hours; then, the remainder of the dose is released at an approximate rate of 5 ug/hour for the remaining 66-hour functional lifetime of the system. The manufacturer states that the initial priming dose saturates binding sites on the skin and rapidly brings the plasma concentration to steady-state. In a crossover study comparing urinary excretion rates of scopolamine during multiple 12-hour collection intervals in healthy individuals, there was no difference between the rates of excretion of drug during steady-state (24-72 hours) for constant-rate IV infusion (3.7-6 mcg/hour) and transdermal administration. The transdermal system appeared to deliver the drug to systemic circulation at the same rate as the constant-rate IV infusion; however, relatively long collection intervals (12 hours) make it difficult to interpret the data precisely. During the 12- to 24-hour period of administration and after 72 hours, the rate of excretion of scopolamine was higher with the transdermal system than with the constant-rate IV infusion.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1323
The distribution of scopolamine has not been fully characterized. The drug appears to be reversibly bound to plasma proteins. Scopolamine apparently crosses the blood-brain barrier since the drug causes CNS effects. The drug also reportedly crosses the placenta and is distributed into milk..
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1323
Although the metabolic and excretory fate of scopolamine has not been fully determined, the drug is thought to be almost completely metabolized (principally by conjugation) in the liver and excreted in urine. Following oral administration of a single dose of scopolamine in one study, only small amounts of the dose (about 4-5%) were excreted unchanged in urine within 50 hours; urinary clearance of unchanged drug was about 120 mL/minute. In another study, 3.4% or less than 1% of a single dose was excreted unchanged in urine within 72 hours following subcutaneous injection or oral administration of the drug, respectively. Following application of a single transdermal scopolamine system that delivered approximately 1 mg/72 hours in healthy individuals, the urinary excretion rate of free and total (free plus conjugated) scopolamine was about 0.7 and 3.8 ug/hour, respectively. Following removal of the transdermal system of scopolamine, depletion of scopolamine bound to skin receptors at the site of the application of the transdermal system results in a log-linear decrease in plasma scopolamine concentrations. Less than 10% of the total dose is excreted in urine as unchanged drug and its metabolites over 108 hours.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1323

8.6 Metabolism / Metabolites

Little is known about the metabolism of scopolamine in humans, although many metabolites have been detected in animal studies. In general, scopolamine is primarily metabolized in the liver, and the primary metabolites are various glucuronide and sulphide conjugates. Although the enzymes responsible for scopolamine metabolism are unknown, _in vitro_ studies have demonstrated oxidative demethylation linked to CYP3A subfamily activity, and scopolamine pharmacokinetics were significantly altered by coadministration with grapefruit juice, suggesting that CYP3A4 is responsible for at least some of the oxidative demethylation.
Although the metabolic and excretory fate of scopolamine has not been fully determined, the drug is thought to be almost completely metabolized (principally by conjugation) in the liver and excreted in urine.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1323

8.7 Biological Half-Life

The half-life of scopolamine differs depending on the route. Intravenous, oral, and intramuscular administration have similar half-lives of 68.7 ± 1.0, 63.7 ± 1.3, and 69.1 ±8/0 min, respectively. The half-life is greater with subcutaneous administration at 213 min. Following removal of the transdermal patch system, scopolamine plasma concentrations decrease in a log-linear fashion with a half-life of 9.5 hours.
Following application of a single transdermal scopolamine system that delivered approximately 1 mg/72 hours, the average elimination half-life of the drug was 9.5 hours.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1323

8.8 Mechanism of Action

[Acetylcholine] (ACh) is a neurotransmitter that can signal through ligand-gated cation channels (nicotinic receptors) and G-protein-coupled muscarinic receptors (mAChRs). ACh signalling via mAChRs located in the central nervous system (CNS) and periphery can regulate smooth muscle contraction, glandular secretions, heart rate, and various neurological phenomena such as learning and memory. mAChRs can be divided into five subtypes, M1-M5, expressed at various levels throughout the brain. Also, M2 receptors are found in the heart and M3 receptors in smooth muscles, mediating effects apart from the direct modulation of the parasympathetic nervous system. While M1, M3, and M5 mAChRs primarily couple to Gq proteins to activate phospholipase C, M2 and M4 mainly couple to Gi/o proteins to inhibit adenylyl cyclase and modulate cellular ion flow. This system, in part, helps to control physiological responses such as nausea and vomiting. Scopolamine acts as a non-selective competitive inhibitor of M1-M5 mAChRs, albeit with weaker M5 inhibition; as such, scopolamine is an anticholinergic with various dose-dependent therapeutic and adverse effects. The exact mechanism(s) of action of scopolamine remains poorly understood. Recent evidence suggests that M1 (and possibly M2) mAChR antagonism at interneurons acts through inhibition of downstream neurotransmitter release and subsequent pyramidal neuron activation to mediate neurological responses associated with stress and depression. Similar antagonism of M4 and M5 receptors is associated with potential therapeutic benefits in neurological conditions such as schizophrenia and substance abuse disorders. The significance of these observations to scopolamine's current therapeutic indications of preventing nausea and vomiting is unclear but is linked to its anticholinergic effect and ability to alter signalling through the CNS associated with vomiting.
Although other antimuscarinics have been used in the prevention of motion sickness, it appears that scopolamine is most effective. Scopolamine apparently corrects some central imbalance of acetylcholine and norepinephrine that may occur in patients with motion sickness. It has been suggested that antimuscarinics may block the transmission of cholinergic impulses from the vestibular nuclei to higher centers in the CNS and from the reticular formation to the vomiting center; these effects result in prevention of motion-induced nausea and vomiting.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1323
The sole active agent of Transderm Scoop is scopolamine, a belladonna alkaloid with well known pharmacological properties. It is an anticholinergic agent which acts: i) as a competitive inhibitor at postganglionic muscarinic receptor sites of the parasympathetic nervous system, and ii) on smooth muscles that respond to acetylcholine but lack cholinergic innervation. It has been suggested that scopolamine acts in the central nervous system (CNS) by blocking cholinergic transmission from the vestibular nuclei to higher centers in the CNS and from the reticular formation to the vomiting center.
Thomson Health Care Inc.; Physicians' Desk Reference 62 ed., Montvale, NJ 2008, p. 2192

8.9 Biochemical Reactions

9 Use and Manufacturing

9.1 Uses

To prevent nausea and vomiting associated with motion sickness
Thomson Health Care Inc.; Physicians' Desk Reference 62 ed., Montvale, NJ 2008, p. 2192
Used to inhibit effects of acetylcholine
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 1110
Sedative ... used to prevent motion sickness and prior to anesthesia /Scopolamine hydrobromide USP/
Osol A, Hoover JE et al, eds; Remington's Pharmaceutical Sciences. 14th ed. Easton, PA: Mack Publishing Co., p. 918 (1975)
THERAP CAT (VET): Preanesthetic medicant
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1450
For more Uses (Complete) data for SCOPOLAMINE (7 total), please visit the HSDB record page.

9.1.1 Use Classification

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

9.2 Methods of Manufacturing

Scopolamine is a tropane alkaloid isolated from Datura metel L., Scopola carniolica Jacq., and other Solanaceae.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V25 166 (2003)

9.3 Impurities

(1R,2R,4S,5S,7s)-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl (2S)-3-hydroxy-2-phenylpropanoate (norhyoscine); (1R,2R,4S,5S,7s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl 2-phenylprop-2-enoate (apohyoscine); (2RS)-3-hydroxy-2-phenylpropanoic acid (DL-tropic acid); hyoscyamine
Council of Europe, European Directorate for the Quality of Medicines. European Pharmacopoeia, 5th Ed., Supplement 5.3; Strasbourg, France, p.3519 (2005)

9.4 Formulations / Preparations

Ophthalmic: Solution: 0.25% Isopto Hyoscine (with benzalkonium chloride; viscous) (Alcon).
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2913
Parenteral: Injection: 0.4 mg/mL Scopolamine Hydrobromide Injection (with parabens), (Abraxis). /Scopolamine hydrobromide/
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1324
Oral: Tablets, soluble: 0.4 mg Scopace, (Hope). /Scopolamine hydrobromide/
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1324
Topical: Transdermal System: approximately 1 mg/72 hours (1.5 mg/2.5 sq cm) Transderm Scop, (Novartis).
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1323

9.5 Consumption Patterns

The transdermal patch contains 12.5 mg of scopolamine.
PDR; Physicians' Desk Reference 50th ed 1996. Montvale,NJ: Medical Economics Co p 869 (1996)

10 Identification

10.1 Analytic Laboratory Methods

COMPARATIVE STUDIES OF COLORIMETRIC, POLAROGRAPHIC, & GAS CHROMATOGRAPHIC METHODS FOR QUANT DETERMINATION OF SCOPOLAMINE IN PHARMACEUTICAL PREPN. GC WAS FAVORED METHOD WITH CAPACITY TO SOLVE ROUTINE ANALYSIS AS WELL AS DIFFICULT PROBLEMS SUCH AS CONTENT UNIFORMITY.
DERTINGER G; ACTA PHARM TECHNOL 25(1) 65-74 (1979)
AUTOMATED PRE-COLUMN DERIVATIZATION SYSTEM & COUPLING OF THIS AUTOANALYZER-TYPE SYSTEM WITH HIGH-PERFORMANCE LIQ CHROMATOGRAPHY IS DISCUSSED. LINEARITY OF SYSTEM FOR HYOSCYAMINE & ERGOTAMINE IS SIGNIFICANT IN CONCN RANGES OF 80-200 NG & 240-720 NG/INJECTION, RESPECTIVELY.
GFELLER ET AL; J CHROMATOGR 166(1) 133-140 (1978)
Analyte: scopolamine hydrobromide; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards /scopolamine hydrobromide/
U.S. Pharmacopeia. The United States Pharmacopeia, USP 31/The National Formulary, NF 26; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p.3220 (2008)
Analyte: scopolamine hydrobromide; matrix: chemical identification; procedure: reaction with chlorine and chloroform; formation of a brownish color /scopolamine hydrobromide/
U.S. Pharmacopeia. The United States Pharmacopeia, USP 31/The National Formulary, NF 26; Rockville, MD: U.S. Pharmacopeial Convention, Inc., p.3220 (2008)
For more Analytic Laboratory Methods (Complete) data for SCOPOLAMINE (19 total), please visit the HSDB record page.

10.2 Clinical Laboratory Methods

Analyte: scopolamine; matrix: blood (whole), urine; procedure: high-performance liquid chromatography with ultraviolet detection at 200.5 nm
Gaillard Y, Pepin G; J Chromatogr A 763: 149-163 (1997). As cited in: Lunn G; HPLC and CE Methods for Pharmaceutical Analysis. CD-ROM. New York, NY: John Wiley & Sons (2000)

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

1 of 4
View All
Pictogram(s)
Acute Toxic
Signal
Danger
GHS Hazard Statements

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

H310 (100%): Fatal in contact with skin [Danger Acute toxicity, dermal]

H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]

Precautionary Statement Codes

P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 14 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Acute Tox. 2 (100%)

Acute Tox. 1 (100%)

Acute Tox. 2 (100%)

Acute Tox. 2 (33.3%)

Acute Tox. 4 (66.7%)

Acute Tox. 1 (33.3%)

Acute Tox. 2 (33.3%)

Repr. 2 (33.3%)

11.1.3 Health Hazards

SYMPTOMS: Symptoms of exposure to this chemical include drowsiness, sleepiness, excitement, hallucinations, delirium, psychotic behavior and central nervous system depression. Other symptoms include narcosis, mydriasis, dryness of the mouth and restlessness. It can also cause temporary loss of accommodation and tachycardia. Dulling of mental alertness may occur. It may also cause irritation.

ACUTE/CHRONIC HAZARDS: This compound may be harmful by ingestion or inhalation. It may cause irritation. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide, nitrogen oxides and hydrogen bromide gas. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.1.4 Fire Hazards

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.2 First Aid Measures

11.2.1 First Aid

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.3 Fire Fighting

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.4 Accidental Release Measures

11.4.1 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

11.5 Handling and Storage

11.5.1 Nonfire Spill Response

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.6 Exposure Control and Personal Protection

11.6.1 Personal Protective Equipment (PPE)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.7 Stability and Reactivity

11.7.1 Air and Water Reactions

Sensitive to air, light and moisture. Water soluble.

11.7.2 Reactive Group

Alcohols and Polyols

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Hydrocarbons, Aromatic

Epoxides

Salts, Acidic

11.7.3 Reactivity Profile

SCOPOLAMINE HYDROBROMIDE is incompatible with acids, bases and oxidizing agents. (NTP, 1992).
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.8 Regulatory Information

REACH Registered Substance
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Hyoscine hydrobromide: Does not have an individual approval but may be used under an appropriate group standard
New Zealand EPA Inventory of Chemical Status
Hyoscine: Does not have an individual approval but may be used under an appropriate group standard

11.8.1 FDA Requirements

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl scopolamine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
DHHS/FDA; Electronic Orange Book-Approved Drug Products with Therapeutic Equivalence Evaluations. Available from, as of October 29, 2008: https://www.fda.gov/cder/ob/
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: scopolamine hydrobromide is included in antidiarrheal drug products. /Scopolamine hydrobromide/
21 CFR 310.545(a) (3) (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of October 24, 2008: https://www.ecfr.gov

11.9 Other Safety Information

11.9.1 Special Reports

Department of Health & Human Services/National Institute of Environmental Health Sciences, National Toxicology Program; Teratologic Evaluation of Scopolamine Hydrobromide (CAS NO. 114-49-8) Administered to CD-1 Mice on Gestational Days 6 Through 15, NTP Study No. TER85107 (April 6, 1987 ) available at http://ntp.niehs.nih.gov/index.cfm?objectid=0847FF31-90CC-C685-88B4D7EAC975BD44 as of August 16, 2002
Toxicology & Carcinogenesis Studies of Scopolamine Hydrobromide in F344/N Rats and B6C3F1 Mice (Gavage Studies). Technical Report Series No. 445 (1997) NIH Publication No. 97-3361 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709
Department of Health & Human Services/National Institute of Environmental Health Sciences, National Toxicology Program; Scopolamine Hydrobromide (CAS NO. 114-49-8) Administered to CD Rats on Gestational Days 6 Through 15, NTP Study No. TER85106 (April 6, 1987 ) available at http://ntp.niehs.nih.gov/index.cfm?objectid=0847FF31-90CC-C685-88B4D7EAC975BD44 as of August 16, 2002

12 Toxicity

12.1 Toxicological Information

12.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

No information is available on the use of scopolamine during breastfeeding. Use during labor appears to have a detrimental effect on newborn infants' nursing behavior. Long-term use of scopolamine might reduce milk production or milk letdown, but a single systemic or ophthalmic dose is not likely to interfere with breastfeeding. During long-term use, observe for signs of decreased lactation (e.g., insatiety, poor weight gain). To substantially diminish the amount of drug that reaches the breastmilk after using eye drops, place pressure over the tear duct by the corner of the eye for 1 minute or more, then remove the excess solution with an absorbent tissue.

◉ Effects in Breastfed Infants

Relevant published information was not found as of the revision date.

◉ Effects on Lactation and Breastmilk

Anticholinergics can inhibit lactation in animals, apparently by inhibiting growth hormone and oxytocin secretion. Anticholinergic drugs can also reduce serum prolactin in nonnursing women. The prolactin level in a mother with established lactation may not affect her ability to breastfeed.

A retrospective case-control study conducted in two hospitals in central Iran compared breastfeeding behaviors in the first 2 hours postdelivery by infants of 4 groups of primiparous women with healthy, full-term singleton births who had vaginal deliveries. The groups were those who received no medications during labor, those who received oxytocin plus scopolamine, those who received oxytocin plus meperidine, and those who received oxytocin, scopolamine and meperidine. The infants in the no medication group performed better than those in all other groups, and the oxytocin plus scopolamine group performed better than the groups that had received meperidine.

12.1.2 Acute Effects

12.1.3 Interactions

Scopolamine should be used with care in patients taking other drugs that are capable of causing CNS effects such as sedatives, tranquilizers, or alcohol. Special attention should be paid to potential interactions with drugs having anticholinergic properties; e.g., other belladonna alkaloids, antihistamines (including meclizine), tricyclic antidepressants, and muscle relaxants.
Thomson Health Care Inc.; Physicians' Desk Reference 62 ed., Montvale, NJ 2008, p. 2192
The absorption of oral medications may be decreased during the concurrent use of scopolamine because of decreased gastric motility and delayed gastric emptying.
Thomson Health Care Inc.; Physicians' Desk Reference 62 ed., Montvale, NJ 2008, p. 2192
Concomitant administration of antimuscarinics and corticosteroids may result in increased intraocular pressure. /Antimuscarinics/Antispasmodics/
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1297
Antacids may decrease the extent of absorption of some oral antimuscarinics when these drugs are administered simultaneously. Therefore, oral antimuscarinics should be administered at least 1 hour before antacids. Antimuscarinics may be administered before meals to prolong the effects of postprandial antacid therapy. However, controlled studies have failed to demonstrate a substantial difference in gastric pH when combined antimuscarinic and antacid therapy was compared with antacid therapy alone. /Antimuscarinics/Antispasmodics/
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1297
For more Interactions (Complete) data for SCOPOLAMINE (8 total), please visit the HSDB record page.

12.1.4 Antidote and Emergency Treatment

Emergency and supportive measures: Maintain an open airway and assist ventilation if needed. Treat hyperthermia, coma, rhabdomyolysis, and seizures if they occur. /Anticholinergics/
Olson, K.R. (Ed.); Poisoning & Drug Overdose. 5th ed. Lange Medical Books/McGraw-Hill. New York, N.Y. 2007., p. 87
Specific drugs and antidotes: A small dose of physostigmine .... can be given to patients with severe toxicity (e.g., hyperthermia, severe delirium, or tachycardia). Caution: Physostigmine can cause AV block, asystole, and seizures, especially in patients with tricyclic antidepressant overdose. Neostigmine, a peripherally acting cholinesterase inhibitor, may be useful in treating anticholinergic-induced ileus. /Anticholinergics/
Olson, K.R. (Ed.); Poisoning & Drug Overdose. 5th ed. Lange Medical Books/McGraw-Hill. New York, N.Y. 2007., p. 87
Decontamination: Administer activated charcoal orally if conditions are appropriate. Gastric lavage is not necessary after small to moderate ingestions if activated charcoal can be given promptly. Because of slowed gastrointestinal motility, gut decontamination procedures may be helpful even in late-presenting patients. /Anticholinergics/
Olson, K.R. (Ed.); Poisoning & Drug Overdose. 5th ed. Lange Medical Books/McGraw-Hill. New York, N.Y. 2007., p. 87
Enhanced elimination: Hemodialysis, hemoperfusion, peritoneal dialysis, and repeat-dose charcoal are not effective in removing anticholinergic agents. /Anticholinergics/
Olson, K.R. (Ed.); Poisoning & Drug Overdose. 5th ed. Lange Medical Books/McGraw-Hill. New York, N.Y. 2007., p. 87
For more Antidote and Emergency Treatment (Complete) data for SCOPOLAMINE (7 total), please visit the HSDB record page.

12.1.5 Human Toxicity Excerpts

/HUMAN EXPOSURE STUDIES/ Scopolamine-induced deficits in cognitive and motor processes have been widely demonstrated in animals and humans, although the role of acetylcholine in working memory is not as well understood. This study examined the role of acetylcholine neurotransmission in visuospatial short term and working memory using the Groton Maze Learning Test (GMLT). The GMLT is a computerized hidden maze learning test that yields measures of component cognitive processes such as spatial memory, working memory, and visuomotor function, as well as their integration in trial-and-error problem solving. Healthy older adults were administered scopolamine (0.3 mg subcutaneous), the acetlycholinesterase inhibitor donepezil (5 mg oral), scopolamine with donepezil, or placebo. Compared to placebo, low-dose scopolamine led to performance deficits on all measures of the GMLT. The greatest scopolamine-induced deficits were observed in errors reflecting working memory processes (e.g., perseverative errors d=-2.98, and rule-break errors d=-2.49) and these impairments remained robust when statistical models accounted for scopolamine-related slowing in visuomotor speed. Co-administration of donepezil partially ameliorated scopolamine-related impairments and this effect was greatest for measures of working memory than short-term memory. By itself, donepezil was associated with a small improvement in visuomotor function. These results suggest that scopolamine disrupts processes required for rule maintenance and performance monitoring, in combination with visuomotor slowing and sequential location learning.
Thomas E et al; Neuropsychologia 46 (10): 2476-84 (2008)
/SIGNS AND SYMPTOMS/ High doses of scopolamine produce CNS effects (e.g., restlessness, disorientation, irritability, hallucinations) similar to those produced by toxic doses of other antimuscarinics.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1323
/SIGNS AND SYMPTOMS/ Scopolamine toxicity usually arises from adulterated products or ingestion of scopolamine-containing plants, producing classic anticholinergic syndrome. Adults as well as children have developed central anticholinergic syndrome with hallucinations and incontinence after being treated with a single transdermal patch.
Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 562
/SIGNS AND SYMPTOMS/ When transdermal scopolamine has been used for longer than 3 days, withdrawal of its use has occasionally been followed by dizziness, nausea, vomiting, headache, and disturbance of equilibrium.
Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 564
For more Human Toxicity Excerpts (Complete) data for SCOPOLAMINE (19 total), please visit the HSDB record page.

12.1.6 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ ... CONCLUSIONS: Under the conditions of these 2 year gavage studies, there was no evidence of carcinogenic activity of scopolamine hydrobromide trihydrate in male or female F344/N rats or B6C3F1 mice administered l, 5, or 25 mg/kg. /Scopolamine hydrobromide/
Toxicology & Carcinogenesis Studies of Scopolamine Hydrobromide in F344/N Rats and B6C3F1 Mice (Gavage Studies). Technical Report Series No. 445 (1997) NIH Publication No. 97-3361 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Reproductive studies in rats and rabbits using IV scopolamine hydrobromide at dosages producing plasma concentrations of the drug 100 times greater than those achievable after application of the transdermal system in humans have shown a marginal embryotoxic effect in rabbits; no teratogenic effects were observed in rats. /Scopolamine hydrobromide/
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1322
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Teratogenic studies were performed in pregnant rats and rabbits with scopolamine hydrobromide administered by daily intravenous injection. No adverse effects were recorded in rats. Scopolamine hydrobromide has been shown to have a marginal embryotoxic effect in rabbits when administered by daily intravenous injection at doses producing plasma levels approximately 100 times the level achieved in humans using a transdermal system. /Scopolamine hydrobromide/
Thomson Health Care Inc.; Physicians' Desk Reference 62 ed., Montvale, NJ 2008, p. 2192
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Fertility studies were performed in female rats and revealed no evidence of impaired fertility or harm to the fetus due to scopolamine hydrobromide administered by daily subcutaneous injection. Maternal body weights were reduced in the highest-dose group (plasma level approximately 500 times the level achieved in humans using a transdermal system). /Scopolamine hydrobromide/
Thomson Health Care Inc.; Physicians' Desk Reference 62 ed., Montvale, NJ 2008, p. 2192
For more Non-Human Toxicity Excerpts (Complete) data for SCOPOLAMINE (6 total), please visit the HSDB record page.

12.1.7 Ongoing Test Status

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. /Scopolamine hydrobromide trihydrate/[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=6533-68-2]

12.1.8 National Toxicology Program Studies

... Male and female F344/N rats and B6C3F1 mice received scopolamine hydrobromide trihydrate (89% pure) in distilled water by gavage for ... or 2 yr. ... 2 YEAR STUDY IN RATS: Groups of 60 male and 60 female rats were administered 0, 1, 5, or 25 mg scopolamine hydrobromide trihydrate/kg body weight in distilled water by gavage for 104 wk. ... 2 YEAR STUDY IN MICE: Groups of 70 male and 70 female mice were administered 0, 1, 5, or 25 mg scopolamine hydrobromide trihydrate/kg body weight in distilled water by gavage for 104 to 105 wk. ... CONCLUSIONS: Under the conditions of these 2 year gavage studies, there was no evidence of carcinogenic activity of scopolamine hydrobromide trihydrate in male or female F344/N rats or B6C3F1 mice administered l, 5, or 25 mg/kg. /Scopolamine hydrobromide trihydrate/
Toxicology & Carcinogenesis Studies of Scopolamine Hydrobromide in F344/N Rats and B6C3F1 Mice (Gavage Studies). Technical Report Series No. 445 (1997) NIH Publication No. 97-3361 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709
Scopolamine hydrobromide (SCOP) ... was evaluated for toxic & teratogenic effects in timed-pregnant CD rats. Animals were exposed to scopolamine hydrobromide in water, by gavage on gestational days (gd) 6-15. Cesarean sections were performed on gestational days 20. Prior to initiation of the teratology study, a preliminary study was conducted in order to establish appropriate doses for use in the teratology study. Based on the results of the preliminary study, doses of 0, 10, 100, 450, & 900 mg/kg/day scopolamine hydrobromide were administered in the teratology study. The teratology study was conducted using a two-replicate design, with 12-16 animals assigned to each dose group in each replicate. The second replicate was started (gestational days 0) 19 days after the first replicate. In each replicate, females were weighed & observed during daily treatment for clinical signs of toxicity. At sacrifice on gestational day 20, the gravid uterus of each dam was weighed. Following uterine dissection the number & status of uterine implantation sites was recorded. Each live fetus was weighed, sexed, & examined for external, visceral, & skeletal malformations. A total of 21-28 dams (i.e., confirmed-pregnant females)/treatment group were evaluated in the study. Exposure of timed-pregnant CD rats to scopolamine hydrobromide dissolved in distilled water (0, 10, 100, 450, or 900 mg/kg/day) by gavage on gestational days 6-15 produced the following results: 1.Observed maternal or developmental toxicity at 10 mg/kg/day. 2.At doses > or = 100 mg/kg/day scopolamine hydrobromide, a marginal non-dose-related reduction in fetal body weight, & a marginal non-dose-related incr in the incidence of malformations/litter in the presence of significant dose-related maternal toxicity (reduced maternal body weight & weight gain). 3.At doses > or = 450 mg/kg/day, exposure to scopolamine hydrobromide was associated with a significant incr in the incidence of short ribs. This effect was observed in the presence of significant maternal toxicity. 4.At the doses tested (0, 10, 100, 450, or 900 mg/kg/day scopolamine hydrobromide) there was no separation of maternal toxicity from developmental toxicity. In conclusion, exposure of timed-pregnant CD rats to scopolamine hydrobromide at doses up to 900 mg/kg/day on gestational days 6-15 caused no clear evidence of teratogenic response in gestational days 20 rat fetuses. Marginal evidence of intrauterine growth retardation, & a non-dose-related trend toward an incr in the incidence of malformations was observed only at doses that caused significant maternal toxicity. /Scopolamine hydrobromide/
Department of Health & Human Services/National Institute of Environmental Health Sciences, National Toxicology Program; Scopolamine Hydrobromide (CAS NO. 114-49-8) Administered to CD Rats on Gestational Days 6 Through 15, NTP Study No. TER85106 (April 6, 1987) Available from, as of August 16, 2002: https://ntp.niehs.nih.gov/index.cfm?objectid=0847FF31-90CC-C685-88B4D7EAC975BD44
Scopolamine hydrobromide (SCOP) ... was evaluated for toxic & teratogenic effects in timed pregnant CD-1 mice. Animals were exposed to scopolamine hydrobromide in water, by gavage on gestational days (gd) 6-15 & sacrificed on /gestational day/ 17. Prior to initiation of the teratology study, a preliminary study was conducted in order to establish appropriate doses for use in the teratology study. Based on the results of the preliminary study, doses of 0, 10, 100, 450, or 900 mg/kg/day scopolamine hydrobromide were administered in the teratology study. The teratology study was conducted using a three-replicate design, with 10-17 animals assigned to each dose group in each replicate. In each replicate, females were weighed & observed during daily treatment for clinical signs of toxicity. At sacrifice on /gestational day/ 17, the gravid uterus of each dam was weighed. Following uterine dissection the number & status of uterine implantation sites was recorded. Each live fetus was weighed, sexed, & examined for external, visceral, & skeletal malformations. A total of 23-32 dams (i.e., confirmed-pregnant females)/treatment group were evaluated in the study. Exposure of timed-pregnant CD-1 mice to scopolamine hydrobromide dissolved in distilled water & administered by gavage at doses of 0, 10, 100, 450, or 900 mg/kg/day on /gestational day/ 6-15 produced the following results: 1) A no effect level for maternal & fetal toxicity at doses of 10 & 100 mg/kg/day. 2) Marginal maternal toxicity, observed as slightly reduced maternal body weight & weight gain determined at the 450 & 900 mg/kg/day doses, with corrected maternal body weight significantly reduced at 900 mg/kg/day. 3) A marginal reduction in avg fetal body weight/litter at 450 & 900 mg/kg/day. 4) Congenital malformations & anatomical variations were observed, at low levels, in all groups. There was no relationship seen between their occurrence & the level of treatment & they were seen with equal frequency throughout the groups studied. Because of this, scopolamine had no observable effect on any measure of embryotoxicity at any dose level. In conclusion, scopolamine hydrobromide administered to pregnant CD-1 mice during the period of major organogenesis at doses up to 900 mg/kg/day had no adverse effect on prenatal viability, produced no evidence of teratogenesis, & caused only a marginal reduction in fetal body weight at doses of 450 & 900 mg/kg/day, that also caused marginal maternal toxicity. /Scopolamine hydrobromide/
Department of Health & Human Services/National Institute of Environmental Health Sciences, National Toxicology Program; Teratologic Evaluation of Scopolamine Hydrobromide (CAS NO. 114-49-8) Administered to CD-1 Mice on Gestational Days 6 Through 15, NTP Study No. TER85107 (April 6, 1987) Available from, as of August 16, 2002: https://ntp.niehs.nih.gov/index.cfm?objectid=0847FF31-90CC-C685-88B4D7EAC975BD44

12.1.9 TSCA Test Submissions

Scopolamine (CAS # 51-34-3) was evaluated for effects on short-term memory. The test substance was administered twice a week to Fischer 344 rats (4/sex/group) at a dosage level of 0, 0.1, 0.15, 0.25, 0.5, and 0.75 mg/kg by intraperitoneal injection at a volume of 1.0 ml/kg body weight. The test substance was administered 20 minutes before testing. Study conduct regarding details on the apparatus and on the conduct on testing may be obtained in Bushnell (1988). The test substance reduced choice accuracy (short-term memory) in a dose-related manner.
HALOGENATED SOLVENTS INDUS; Validation With Scopolamine And Methscopolamine of a Test of Short-Term Memory in Rats (Draft Report) With Attachments and Cover Letter Dated 03/07/91; EPA Doc No. 40-9124611; Fiche No. OTS0533135

12.1.10 Populations at Special Risk

Scopolamine generally is contraindicated in patients with glaucoma (i.e., angle-closure), pyloric obstruction, or urinary bladder neck obstruction. Scopolamine generally also is contraindicated in patients with tachycardia secondary to cardiac insufficiency or thyrotoxicosis and in those with paralytic ileus. The manufacturer states that scopolamine hydrobromide soluble tablets are contraindicated in patients with prostatic hypertrophy or impaired renal or hepatic function. Scopolamine is contraindicated in patients who are hypersensitive to the drug, to any other belladonna alkaloid, or to any ingredient or component in the formulation or administration system.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1322
Transdermal scopolamine should be used with caution in patients with a history of seizures or psychosis, since the drug potentially can aggravate these conditions.
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1322
Scopolamine hydrobromide should be used with extreme caution, if at all, in infants and small children. /Scopolamine hydrobromide/
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 2913
A transdermal scopolamine patch should not be used in the pediatric population, and with extreme caution in the elderly.
Holland MS; Nurse Anesth 3 (3): 121-4 (1992)
For more Populations at Special Risk (Complete) data for SCOPOLAMINE (7 total), please visit the HSDB record page.

12.1.11 Protein Binding

Scopolamine may reversibly bind plasma proteins in humans. In rats, scopolamine exhibits relatively low plasma protein binding of 30 ± 10%.

12.2 Ecological Information

12.2.1 Natural Pollution Sources

A solanaceous alkaloid derivative from members of the plant genera Erythoxylon, Atropa, Datura, Hyoscyamus, and Scopola. The percent of total alkaloid in the leaves of Datura stramonium is 0.25-0.55%.
Osol A, Hoover JE et al, eds; Remington's Pharmaceutical Sciences. 14th ed. Easton, PA: Mack Publishing Co., p. 489, 496 (1975)

12.2.2 Milk Concentrations

The distribution of scopolamine has not been fully characterized. The drug appears to be reversibly bound to plasma proteins. Scopolamine apparently crosses the blood-brain barrier since the drug causes CNS effects. The drug also reportedly crosses the placenta and is distributed into milk..
American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 1323

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Wiley References

14.6 Nature Journal References

14.7 Chemical Co-Occurrences in Literature

14.8 Chemical-Gene Co-Occurrences in Literature

14.9 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Protein Bound 3D Structures

16.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

16.2 Chemical-Target Interactions

16.3 Drug-Drug Interactions

16.4 Drug-Food Interactions

Avoid grapefruit products. Coadministration of scopolamine with grapefruit juice has been shown to delay scopolamine absorption and increase its bioavailability without altering its elimination.

16.5 Pathways

17 Biological Test Results

17.1 BioAssay Results

18 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
S29 | PHYTOTOXINS | Toxic Plant Phytotoxin (TPPT) Database | DOI:10.5281/zenodo.2652993

19 Classification

19.1 MeSH Tree

19.2 NCI Thesaurus Tree

19.3 ChEBI Ontology

19.4 WHO ATC Classification System

19.5 FDA Pharm Classes

19.6 ChemIDplus

19.7 CAMEO Chemicals

19.8 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

19.9 ChEMBL Target Tree

19.10 UN GHS Classification

19.11 NORMAN Suspect List Exchange Classification

19.12 CCSBase Classification

19.13 EPA DSSTox Classification

19.14 LOTUS Tree

19.15 MolGenie Organic Chemistry Ontology

20 Information Sources

  1. CAMEO Chemicals
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    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
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    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
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  7. Hazardous Substances Data Bank (HSDB)
  8. New Zealand Environmental Protection Authority (EPA)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  11. LOTUS - the natural products occurrence database
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    https://lotus.nprod.net/
  12. NCI Thesaurus (NCIt)
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    https://www.cancer.gov/policies/copyright-reuse
  13. Open Targets
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    https://platform-docs.opentargets.org/licence
  14. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  15. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  16. Comparative Toxicogenomics Database (CTD)
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    http://ctdbase.org/about/legal.jsp
  17. Drug Gene Interaction database (DGIdb)
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    http://www.dgidb.org/downloads
  18. IUPHAR/BPS Guide to PHARMACOLOGY
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    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  19. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  20. Therapeutic Target Database (TTD)
  21. DailyMed
  22. IUPAC Digitized pKa Dataset
  23. Drugs and Lactation Database (LactMed)
  24. Drugs@FDA
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  26. EU Clinical Trials Register
  27. Hazardous Chemical Information System (HCIS), Safe Work Australia
  28. Regulation (EC) No 1272/2008 of the European Parliament and of the Council
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    https://eur-lex.europa.eu/content/legal-notice/legal-notice.html
  29. FDA Orange Book
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  30. NORMAN Suspect List Exchange
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    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Scopolamine
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  31. National Drug Code (NDC) Directory
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  32. MassBank of North America (MoNA)
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    https://mona.fiehnlab.ucdavis.edu/documentation/license
  33. Kruve Lab, Ionization & Mass Spectrometry, Stockholm University
    scopolamine
  34. Natural Product Activity and Species Source (NPASS)
  35. MassBank Europe
  36. Metabolomics Workbench
  37. Nature Chemical Biology
  38. NIPH Clinical Trials Search of Japan
  39. NLM RxNorm Terminology
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  40. WHO Anatomical Therapeutic Chemical (ATC) Classification
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  42. Protein Data Bank in Europe (PDBe)
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  50. PubChem
  51. GHS Classification (UNECE)
  52. MolGenie
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    https://github.com/MolGenie/ontology/
  53. PATENTSCOPE (WIPO)
  54. NCBI
CONTENTS