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Levomethorphan

PubChem CID
5362449
Structure
Levomethorphan_small.png
Levomethorphan_3D_Structure.png
Molecular Formula
Synonyms
  • Levomethorphan
  • l-Methorphan
  • Methorphan
  • Levomethorphane
  • Levometorfano
Molecular Weight
271.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
Levomethorphan is a 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the stereocenters at positions 4a, 10 and 10a have R-configuration. It is a prodrug of levorphanol and a strong narcotic analgesic, and listed as a schedule II controlled substance. It has a role as an opioid analgesic and a prodrug. It is functionally related to a Levorphanol. It is an enantiomer of a dextromethorphan.
Levomethorphan is a DEA Schedule II controlled substance. Substances in the DEA Schedule II have a high potential for abuse which may lead to severe psychological or physical dependence. It is a Opiates substance.
Racemethorphan is a DEA Schedule II controlled substance. Substances in the DEA Schedule II have a high potential for abuse which may lead to severe psychological or physical dependence. It is a Opiates substance.
See also: Dextromethorphan (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Levomethorphan.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

MKXZASYAUGDDCJ-CGTJXYLNSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CN1CC[C@]23CCCC[C@H]2[C@H]1CC4=C3C=C(C=C4)OC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C18H25NO
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

125-71-3
524713-56-2

2.3.2 Deprecated CAS

1527-45-3, 3894-26-6, 5822-42-4, 879724-84-2

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DEA Code Number

9210 (DEA schedule II controlled substance)
9732 (DEA schedule II controlled substance)

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 KEGG ID

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 NSC Number

2.3.14 Wikidata

2.3.15 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • l-methorphan
  • levomethorphan

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
271.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
271.193614421 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
271.193614421 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
12.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
370
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
3
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

Solid

3.2.2 Solubility

8.51 mg/L

3.2.3 LogP

3.6

3.2.4 Kovats Retention Index

Standard non-polar
2165 , 2155

3.3 Chemical Classes

3.3.1 Drugs

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; Antitussive Agents

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
CD3OD
pH
7.00
Shifts [ppm]:Intensity
1.43:2.33, 1.60:3.44, 1.93:1.31, 1.14:2.58, 1.12:0.84, 1.27:0.45, 6.83:6.06, 1.74:1.51, 6.84:5.29, 1.62:3.51, 1.49:0.54, 1.42:1.58, 1.33:1.50, 1.61:1.94, 1.73:1.64, 2.73:0.88, 1.44:3.07, 1.13:2.45, 6.88:10.38, 1.71:2.35, 1.32:2.16, 1.45:1.89, 1.33:1.02, 1.27:0.65, 2.06:1.28, 3.63:4.09, 2.52:2.53, 1.47:0.48, 3.17:6.22, 7.17:6.43, 1.72:1.14, 1.28:1.47, 1.40:1.20, 1.47:1.61, 1.11:0.74, 3.63:4.03, 1.41:1.13, 1.44:2.45, 2.50:2.64, 1.71:2.23, 1.31:3.13, 7.16:6.91, 1.34:1.02, 1.62:3.77, 1.60:3.81, 1.46:2.55, 1.29:2.41, 1.16:2.84, 1.18:1.13, 6.85:6.89, 1.18:1.10, 1.29:1.69, 1.16:2.77, 1.57:1.94, 1.91:0.78, 1.48:0.80, 3.78:100.00, 1.73:2.09, 6.83:4.89, 1.72:1.82, 1.55:2.05, 1.26:0.36, 1.43:2.52, 1.42:2.45, 2.94:10.40, 1.95:0.78, 6.88:9.27, 1.40:1.29, 2.04:1.27, 3.15:2.09, 1.31:2.00
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4.1.2 13C NMR Spectra

Instrument Name
Varian NV-14
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
CD3OD
pH
7.00
Shifts [ppm] (F2:F1):Intensity
2.93:41.17:0.60, 3.77:55.77:1.00, 1.43:36.20:0.18, 6.84:113.87:0.39, 2.06:44.17:0.01, 7.16:130.47:0.36, 1.61:22.92:0.14, 1.14:26.90:0.09, 3.62:61.76:0.51, 1.72:26.90:0.17, 2.72:48.82:0.02, 3.17:24.24:0.04, 1.29:22.92:0.06, 1.55:26.90:0.15, 6.88:111.88:0.98, 3.15:48.82:0.05, 1.93:40.52:0.01, 1.45:26.90:0.10, 2.51:36.20:0.09, 1.60:40.52:0.02
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 5
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

59.0 99.99

271.0 38

150.0 34.40

214.0 20.30

31.0 19.70

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Notes
instrument=HITACHI RMU-6E
2 of 5
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI RMU-6E
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

59 99.99

271 38

150 34.40

214 20.30

31 19.70

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License
CC BY-NC-SA

4.3.2 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Instrument Type
Quattro_QQQ
Ionization Mode
N/A
Top 5 Peaks

279.253 100

195.291 23.94

276.872 21.62

176.245 21.04

358.469 19.88

Thumbnail
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2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Instrument Type
Quattro_QQQ
Ionization Mode
N/A
Top 5 Peaks

80.904 100

82.282 91.99

212.708 54.60

181.382 28.44

232.132 22.02

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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Classes

Breast Feeding; Lactation; Milk, Human; Antitussive Agents

7.2 DEA Drug and Chemical Information

7.2.1 DEA Controlled Substances

1 of 2
Substance
Levomethorphan
DEA Controlled Substances Code Number
9210
Controlled Substances Act Schedule
Schedule II - Substances in the DEA Schedule II have a high potential for abuse which may lead to severe psychological or physical dependence.
Class
Opiates
2 of 2
Substance
Racemethorphan
DEA Controlled Substances Code Number
9732
Controlled Substances Act Schedule
Schedule II - Substances in the DEA Schedule II have a high potential for abuse which may lead to severe psychological or physical dependence.
Class
Opiates

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Analgesics, Opioid
Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)
Narcotics
Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS. (See all compounds classified as Narcotics.)

8.2 Metabolism / Metabolites

Hepatic. Rapidly and extensively metabolized to dextrorphan (active metabolite). One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6. Half Life: 3-6 hours

8.3 Human Metabolite Information

8.3.1 Cellular Locations

Membrane

9 Use and Manufacturing

9.1 Uses

The primary use of dextromethorphan is as a cough suppressant, for the temporary relief of cough caused by minor throat and bronchial irritation (as commonly accompanies the common cold), as well as those resulting from inhaled irritants. In addition, a combination of dextromethorphan and quinidine has been shown to alleviate symptoms of easy laughing and crying (pseudobulbar affect) in patients with amyotrophic lateral sclerosis and multiple sclerosis.

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement Codes

P264, P270, P301+P317, P330, 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 39 reports by companies from 2 notifications to the ECHA C&L Inventory.

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.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (97.4%)
Acute Tox. 3 (100%)

10.2 Regulatory Information

DEA Controlled Substances
DEA schedule II controlled substance

11 Toxicity

11.1 Toxicological Information

11.1.1 Toxicity Summary

Dextromethorphan is an opioid-like drug that binds to and acts as antagonist to the NMDA glutamatergic receptor, it is an agonist to the opioid sigma 1 and sigma 2 receptors, it is also an alpha3/beta4 nicotinic receptor antagonist and targets the serotonin reuptake pump. Dextromethorphan is rapidly absorbed from the gastrointestinal tract, where it enters the bloodstream and crosses the blood-brain barrier. The first-pass through the hepatic portal vein results in some of the drug being metabolized into an active metabolite of dextromethorphan, dextrorphan, the 3-hydroxy derivative of dextromethorphan.

11.1.2 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

11.1.3 Health Effects

Hypertension, shallow respiration. Dextromethorphan can cause other gastrointestinal disturbances. [Wikipedia]

11.1.4 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

The amounts of dextromethorphan and its active metabolite in breastmilk are very low and are not expected to affect the nursing infant. It is best to avoid the use of products with a high alcohol content while nursing.

◉ Effects in Breastfed Infants

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

◉ Effects on Lactation and Breastmilk

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

11.1.5 Exposure Routes

Oral, rapidly absorbed from the gastrointestinal tract.

11.1.6 Symptoms

symptoms include vomitting, drowiness, diarrhea, urinary retention, fever, and sweating. [Wikipedia]

11.1.7 Acute Effects

11.1.8 Toxicity Data

LD50: 165 mg/kg (mice) (L1858) LD50: 350 mg/kg (rat) (L1858)
L1858: IPCS Inchem monograph for Dextromethorphan http://www.inchem.org/documents/pims/pharm/pim179.htm

12 Associated Disorders and Diseases

Disease
Peripheral neuropathy
References

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-Gene Co-Occurrences in Literature

13.6 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 Interactions and Pathways

15.1 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

18 Classification

18.1 MeSH Tree

18.2 NCI Thesaurus Tree

18.3 ChEBI Ontology

18.4 KEGG: Target-based Classification of Drugs

18.5 KEGG: Drug Groups

18.6 ChemIDplus

18.7 ChEMBL Target Tree

18.8 UN GHS Classification

18.9 Drug Enforcement Administration (DEA) Classification

18.10 NORMAN Suspect List Exchange Classification

18.11 EPA DSSTox Classification

18.12 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
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    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  8. ChEBI
  9. Drug Enforcement Administration (DEA)
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    https://www.justice.gov/legalpolicies
    DEA drug and chemical classification
    https://www.dea.gov/drug-information/drug-scheduling
  10. Toxin and Toxin Target Database (T3DB)
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    http://www.t3db.ca/downloads
  11. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  12. Drugs and Lactation Database (LactMed)
  13. MassBank of North America (MoNA)
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    https://mona.fiehnlab.ucdavis.edu/documentation/license
  14. SpectraBase
  15. KEGG
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    https://www.kegg.jp/kegg/legal.html
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
  16. Metabolomics Workbench
  17. Natural Product Activity and Species Source (NPASS)
  18. NCI Thesaurus (NCIt)
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  19. NIST Mass Spectrometry Data Center
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    https://www.nist.gov/srd/public-law
  20. 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/
    Racemethorphan
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  21. Springer Nature
  22. Thieme Chemistry
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    https://www.nlm.nih.gov/copyright.html
  27. GHS Classification (UNECE)
  28. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  29. PATENTSCOPE (WIPO)
  30. NCBI
CONTENTS