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Clortermine

PubChem CID
25223
Structure
Clortermine_small.png
Clortermine_3D_Structure.png
Molecular Formula
Synonyms
  • CLORTERMINE
  • 10389-73-8
  • Clortermine [INN]
  • 1-(2-chlorophenyl)-2-methylpropan-2-amine
  • Clortermina
Molecular Weight
183.68 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-04
Description
Clortermine is a member of amphetamines.
Clortermine is a DEA Schedule III controlled substance. Substances in the DEA Schedule III have a potential for abuse less than substances in Schedules I or II and abuse may lead to moderate or low physical dependence or high psychological dependence. It is a Stimulants substance.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Clortermine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-(2-chlorophenyl)-2-methylpropan-2-amine
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H14ClN/c1-10(2,12)7-8-5-3-4-6-9(8)11/h3-6H,7,12H2,1-2H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

HXCXASJHZQXCKK-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC(C)(CC1=CC=CC=C1Cl)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H14ClN
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DEA Code Number

1647 (DEA schedule III controlled substance)

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 Metabolomics Workbench ID

2.3.9 NCI Thesaurus Code

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.3.12 Wikipedia

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
183.68 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.5
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
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
183.0814771 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
183.0814771 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
26 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
145
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
0
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 Boiling Point

116-118 °C @ 16 MM HG
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 377

3.2.2 Melting Point

245-246
Finocchio, D.V.and Heubner, C.F.; U.S. Patent 3,415,937; December 10,1968; assigned to Ciba Corporation.
CRYSTALS FROM ETHANOL; MP: 245-246 °C /CLORTERMINE HYDROCHLORIDE/
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 377

3.2.3 Kovats Retention Index

Standard non-polar
1305 , 1305

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

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 4
View All
NIST Number
334905
Library
Main library
Total Peaks
73
m/z Top Peak
58
m/z 2nd Highest
42
m/z 3rd Highest
125
Thumbnail
Thumbnail
2 of 4
View All
NIST Number
247654
Library
Replicate library
Total Peaks
72
m/z Top Peak
58
m/z 2nd Highest
168
m/z 3rd Highest
125
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 DEA Drug and Chemical Information

7.1.1 DEA Controlled Substances

Substance
Clortermine
DEA Controlled Substances Code Number
1647
Controlled Substances Act Schedule
Schedule III - Substances in the DEA Schedule III have a potential for abuse less than substances in Schedules I or II and abuse may lead to moderate or low physical dependence or high psychological dependence.
Class
Stimulants

7.2 Therapeutic Uses

AN ANORECTIC DRUG SIMILAR TO CHLORPHENTERMINE. ALTHOUGH IT IS A SYMPATHOMIMETIC, CARDIOVASCULAR ACTIONS ARE USUALLY MINIMAL IN THERAPEUTIC DOSES. LIKE OTHER DRUGS IN THIS CLASS, CONTROL OF APPETITE IS MAINTAINED FOR ONLY A FEW WEEKS & ... IS NO SUBSTITUTE FOR RETRAINING IN EATING HABITS. /CLORTERMINE HYDROCHLORIDE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 822
IT SHOULD BE PRESCRIBED ONLY AS A SHORT-TERM ADJUNCT (FOUR TO SIX WEEKS) IN A PROGRAM THAT ALSO INCLUDES CALORIC RESTRICTION, APPROPRIATE EXERCISE, & PSYCHOLOGIC SUPPORT. /CLORTERMINE HYDROCHLORIDE/
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 493
CONTROLLED STUDIES IN PT WITH CARDIOVASCULAR DISEASES HAVE FAILED TO DEMONSTRATE THAT ... /CLORTERMINE/ HAS A SIGNIFICANT EFFECT ON BLOOD PRESSURE, PULSE, OR ELECTROCARDIOGRAPHIC READINGS. ... THERE IS EVIDENCE TO SUGGEST THAT CONTROL OF DIABETES MELLITUS IS NOT ADVERSELY AFFECTED BY CLORTERMINE. /CLORTERMINE HYDROCHLORIDE/
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 493

7.3 Drug Warnings

THE DRUG HAS A POTENTIAL FOR ABUSE. ... CLORTERMINE IS CONTRAINDICATED IN AGITATED STATES, HYPERTHYROIDISM, GLAUCOMA, HYPERSENSITIVITY, OR IDIOSYNCRASY TO OTHER SYMPATHOMIMETIC DRUGS. IT SHOULD BE USED CAUTIOUSLY IN PT WITH HYPERTENSION OR CARDIOVASCULAR DISEASE. /CLORTERMINE HYDROCHLORIDE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 822
THE DRUG MAY ALTER INSULIN REQUIREMENTS IN DIABETES MELLITUS. IT SHOULD NOT BE USED WHEN THERE IS A HISTORY OF DRUG ABUSE. ... DRUG IS NOT ADVISED FOR USE IN CHILDREN. /CLORTERMINE HYDROCHLORIDE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 822
... CLORTERMINE SHOULD NOT BE USED IN PT WHO ARE RECEIVING ... /GUANETHIDINE OR MONOAMINE OXIDASE INHIBITORS/. /CLORTERMINE HYDROCHLORIDE/
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 493
THE MANIFESTATIONS OF CHRONIC INTOXICATION & OVERDOSAGE WITH CLORTERMINE MAY CLOSELY RESEMBLE THOSE ASSOCIATED WITH ABUSE & OVERUSE OF AMPHETAMINES. /CLORTERMINE HYDROCHLORIDE/
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 493
For more Drug Warnings (Complete) data for CLORTERMINE (7 total), please visit the HSDB record page.

8 Pharmacology and Biochemistry

8.1 Biological Half-Life

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 65

8.2 Mechanism of Action

/CLORTERMINE/ ... IS THE ORTHO-CHLORO ISOMER OF CHLORPHENTERMINE HYDROCHLORIDE, TO WHICH IT IS COMPARABLE IN SUPPRESSING APPETITE. /CLORTERMINE HYDROCHLORIDE/
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 493

9 Use and Manufacturing

9.1 Uses

MEDICATION

9.2 Formulations / Preparations

CHLOROPHENETHYLAMINE HYDROCHLORIDE; S 77 /CLORTERMINE HYDROCHLORIDE/
U.S. Department of Health, Education & Welfare, Public Health Service. Center for Disease Control, National Institute for Occupational Safety & Health. Registry of Toxic Effects of Chemical Substances. 1978 edition. Washington, DC: U.S. Government Printing Office, 1979., p. 888

10 Identification

10.1 Clinical Laboratory Methods

Applications of capillary gas chromatography in routine toxicological analyses. /Clortermine is one of the substances identified/.
Anderson WH, Stafford DT; J High Resol Chromatogr Chromatogr Commun 6 (5): 247-54 (1983)

11 Safety and Hazards

11.1 Regulatory Information

DEA Controlled Substances
DEA schedule III controlled substance

11.1.1 FDA Requirements

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
21 CFR 200-299, 300-499, 820, and 860 (4/1/91
Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule III includes clortermine, DEA Code #1647; Drug class: Stimulant.
21 CFR 1308.13(b) (4/1/91)
Drugs; statement of required warning. The label of any drug listed as a "controlled substance" in schedule II, III, or IV of the Federal Controlled Substances Act shall, when dispensed to or for a patient, contain the following warning: "Caution: Federal law prohibits the transfer of this drug to any person other than the patient for whom it was prescribed." This statement is not required to appear on the label of a controlled substance for use in clinical investigations which are "blind".
21 CFR 290.5 (4/1/91)

12 Toxicity

12.1 Toxicological Information

12.1.1 Toxicity Summary

IDENTIFICATION: Clortermine hydrochloride is a centrally acting antiobesity drug. It is an amphetamine derivative and misused for performance enhancement and relief of fatigue. Its abuse is either orally or by injection. HUMAN EXPOSURE: Main risks and target organs: Acute central nervous system stimulation, cardiotoxicity causing tachycardia, arrhythmias, hypertension and cardiovascular collapse. High risk of dependency and abuse. Summary of clinical effects: Cardiovascular: Palpitation, chest pain, tachycardia, arrhythmias and hypertension are common; cardiovascular collapse can occur in severe poisoning. Myocardial ischaemia, infarction and ventricular dysfunction are described. Central Nervous System (CNS): Stimulation of CNS, tremor, restlessness, agitation, insomnia, increased motor activity, headache, convulsions, coma and hyperreflexia are described. Stroke and cerebral vasculitis have been observed. Gastrointestinal: Vomiting, diarrhea and cramps may occur. Genitourinary: Increased bladder sphincter tone may cause dysuria, hesitancy and acute urinary retention. Renal failure can occur secondary to dehydration or rhabdomyolysis. Renal ischemia may be noted. Dermatologic: Skin is usually pale and diaphoretic, but mucous membranes appear dry. Endocrine: Transient hyperthyroxinemia may be noted. Metabolism: Increased metabolic and muscular activity may result in hyperventilation and hyperthermia. Weight loss is common with chronic use. Fluid/Electrolyte: Hypo- and hyperkalemia have been reported. Dehydration is common. Musculoskeletal: Fasciculations and rigidity may be noted. Rhabdomyolysis is an important consequence of severe poisoning. Psychiatric: Agitation, confusion, mood elevation, increased wakefulness, talkativeness, irritability and panic attacks are typical. Chronic abuse can cause delusions and paranoia. A withdrawal syndrome occurs after abrupt cessation following chronic use. Contraindications: Anorexia, insomnia, psychopathic personality disorders, suicidal tendencies, Tourette syndrome and other disorders, hyperthyroidism, narrow angle glaucoma, diabetes mellitis and cardiovascular diseases such as angina, hypertension and arrythmias.Interacts with several other CNS stimulant drugs. Routes of exposure: Oral: Readily absorbed from the gastro-intestinal tract and buccal mucosa. It is resistant to metabolism by monoamine oxidase. Inhalation: Rapidly absorbed by inhalation and is abused by this route. Parenteral: Frequent route of entry in abuse situations. Absorption by route of exposure: Rapidly absorbed after oral ingestion. Peak plasma levels occur within 1 to 3 hours, varying with the degree of physical activity and the amount of food in the stomach. Absorption is usually complete by 4 to 6 hours. Sustained release preparations are available as resin bound, rather than soluble, salts. These compounds display reduced peak blood levels compared with standard preparations, but total amount absorbed and time to peak levels remain similar. Distribution by route of exposure: Concentrated in the kidney, lungs, cerebrospinal fluid and brain. Highly lipid soluble and readily cross the blood-brain barrier. Protein binding and volume of distribution varies widely, but the average volume of distribution is 5 L/kg body weight. Biological half-life by route of exposure: Under normal conditions, about 30% is excreted unchanged in the urine but this excretion is highly variable and is dependent on urinary pH. When the urinary pH is acidic (pH 5.5 to 6.0), elimination is predominantly by urinary excretion with approximately 60% of a dose being excreted unchanged by the kidney within 48 hours. When the urinary pH is alkaline (pH 7.5 to 8.0), elimination is predominantly by deamination (less than 7% excreted unchanged in the urine); the half-life ranging from 16 to 31 hours. Metabolism: The major metabolic pathway involves deamination by cytochrome P450 to the para-hydroxy compound and its congener phenylacetone; this latter compound is subsequently oxidized to chloro benzoic acid and excreted as glucuronide or glycine (hippuric acid) conjugate. Smaller amounts are converted to chloronorephedrine by oxidation. Hydroxylation produces an active metabolite, O-hyroxynorephedrine, which acts as a false neurotransmitter and may account for some drug effect, especially in chronic users. Elimination and excretion: Normally 5 to 30% of a therapeutic dose is excreted unchanged in the urine by 24 hours, but the actual amount of urinary excretion and metabolism is highly pH dependent. Mode of action: Toxicodynamics: Appears to exert most or all of its effect in the CNS by causing release of biogenic amines, especialy norepinephrine and dopamine, from storage sites in nerve terminals. It may also slow down catecholamine metabolism by inhibiting monoamine oxidase. Teratogenicity: Use of the compound for medical indications does not pose a significant risk to the fetus for congenital anomalies. Mild withdrawal symptoms may be observed in the newborn, but the few studies of infant follow-up have not shown long-term sequele, although more studies of this nature are needed. Illicit maternal use or abuse presents a significant risk to the fetus and newborn, including intrauterine growth retardation, premature delivery and the potential for increased maternal, fetal and neonatal morbidity. These poor outcomes are probably multifactorial in origin, involving multiple drug use, life-styles and poor maternal health. However, cerebral injuries occurring in newborns exposed in utero appear to be directly related to the vasoconstrictive properties of the compound. Those children exposed throughout pregnancy tended to be more aggressive. Interactions: Acetazolamide: administration may increase serum concentration. Alcohol: may increase serum concentration. Ascorbic acid: lowering urinary pH, may enhance excretion. Furazolidone: May induce a hypertensive response in patients taking furazolidone. Guanethidine: Inhibits the antihypertensive response to guanethidine. Haloperidol: limited evidence indicates that haloperidol may inhibit the effects but the clinical importance of this interaction is not established. Lithium carbonate: isolated case reports indicate that lithium may inhibit the effects. Monoamine oxidase inhibitor: severe hypertensive reactions have followed the administration to patients taking monoamine oxidase inhibitors. Norepinephrine: Abuse may enhance the pressor response to norepinephrine. Phenothiazines: May inhibit the antipsychotic effect of phenothiazines, and phenothiazines may inhibit the anorectic effect. Sodium bicarbonate: large doses of sodium bicarbonate inhibit its elimination, thus increasing the effect. Tricyclic antidepressants: theoretically increases the effect, but clinical evidence is lacking. /Clortermine hydrochloride/
International Programme on Chemical Safety; Poisons Information Monograph: Clortermine Hydrochloride (PIM 936) (1998) Available from, as of December 6, 2005: https://www.inchem.org/pages/pims.html

12.1.2 Antidote and Emergency Treatment

Diazepam may be given to control central nervous system stimulation and convulsions. For marked excitement or hallucinations chlorpromazine may be necessary and, in addition, its alpha-adrenoceptor blocking properties may be useful for the management of hypertension. Severe hypertension may call for the administration of an alpha-adrenoceptor blocking agent, such as phentolamine. Measures should be taken to control increased body temperature.
Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 362

12.1.3 Human Toxicity Excerpts

CARDIOVASCULAR SIDE EFFECTS INCL TACHYCARDIA, PALPITATION, & HYPERTENSION. UNTOWARD EFFECTS ON NERVOUS SYSTEM INCL RESTLESSNESS, EXCITEMENT, INSOMNIA, EUPHORIA, DYSPHORIA, DIZZINESS, TREMOR, HEADACHE, & RARE PSYCHOTIC EPISODES. /CLORTERMINE HYDROCHLORIDE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 822
OTHER SIDE EFFECTS INCL XEROSTOMIA, UNPLEASANT TASTE, CONSTIPATION, DIARRHEA, GI UPSETS, URTICARIA, IMPOTENCE, & DIMINISHED LIBIDO. /CLORTERMINE HYDROCHLORIDE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 822
WHEN AMT SUBSTANTIALLY LARGER THAN CLINICAL DOSAGE WERE ADMIN TO VOLUNTEERS, CHILLS, DIZZINESS, NAUSEA, & TREMORS (BUT NO CARDIOVASCULAR EFFECTS) OBSERVED. /CHLORTERMINE HYDROCHLORIDE/
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 493
Excessive use may lead to tolerance and physical dependence.
Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 377

13 Literature

13.1 Consolidated References

13.2 Springer Nature References

13.3 Thieme References

13.4 Chemical Co-Occurrences in Literature

13.5 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 NCI Thesaurus Tree

16.2 ChEBI Ontology

16.3 ChemIDplus

16.4 Drug Enforcement Administration (DEA) Classification

16.5 NORMAN Suspect List Exchange Classification

16.6 EPA DSSTox Classification

16.7 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. Hazardous Substances Data Bank (HSDB)
  7. ChEBI
  8. Drug Enforcement Administration (DEA)
    LICENSE
    Unless otherwise indicated, information on Department of Justice websites is in the public domain and may be copied and distributed without permission. Citation of the Department of Justice as source of the information is appreciated, as appropriate.
    https://www.justice.gov/legalpolicies
    DEA drug and chemical classification
    https://www.dea.gov/drug-information/drug-scheduling
  9. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. Metabolomics Workbench
  12. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  13. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  14. SpectraBase
    Benzeneethanamine, 2-chloro-.alpha.,.alpha.-dimethyl-
    https://spectrabase.com/spectrum/D4EnB6k1Jyg
  15. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Clortermine
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  16. Springer Nature
  17. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  18. Wikidata
  19. Wikipedia
  20. PubChem
  21. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  22. PATENTSCOPE (WIPO)
  23. NCBI
CONTENTS