Levomethorphan

Levomethorphan
Clinical data
Dependence; liability	High
Addiction; liability	High
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule II;
Pharmacokinetic data
Elimination half-life	3-6 hours
Identifiers
	IUPAC name (1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene;
CAS Number	125-70-2 ;
PubChem CID	5362449;
ChemSpider	4642423 ;
UNII	7ZZ22K9QE6;
KEGG	D12696 ;
ChEBI	CHEBI:146176 ;
ChEMBL	ChEMBL1908323 ;
CompTox Dashboard (EPA)	DTXSID20872403 ;
ECHA InfoCard	100.004.320
Chemical and physical data
Formula	C18H25NO
Molar mass	271.404 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1ccc2C[C@@H]3[C@@H]4CCCC[C@]4(CCN3C)c2c1;
	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 ; Key:MKXZASYAUGDDCJ-CGTJXYLNSA-N ;
	(what is this?) (verify)

Levomethorphan (LVM) (INN, BAN) is an opioid analgesic of the morphinan family that has never been marketed.^[2] It is the L-stereoisomer of racemethorphan (methorphan).^[2] The effects of the two isomers of racemethorphan are quite different, with dextromethorphan (DXM) being an antitussive at low doses and a dissociative hallucinogen at much higher doses.^[3] Levomethorphan is about five times stronger than morphine.^[4]

Levomethorphan is a prodrug to levorphanol, analogously to DXM acting as a prodrug to dextrorphan or codeine behaving as a prodrug to morphine.^[5] As such, levomethorphan has similar effects to levorphanol but is less potent as it must be demethylated to the active form by liver enzymes before being able to produce its effects.^[5] As a prodrug of levorphanol, levomethorphan functions as a potent agonist of all three of the opioid receptors, μ, κ (κ₁ and κ₃ but notably not κ₂), and δ, as an NMDA receptor antagonist, and as a serotonin-norepinephrine reuptake inhibitor.^[5] Via activation of the κ-opioid receptor, levomethorphan can produce dysphoria and psychotomimetic effects such as dissociation and hallucinations.^[6]

Levomethorphan is listed under the Single Convention on Narcotic Drugs 1961 and is regulated like morphine in most countries. In the United States it is a Schedule II Narcotic controlled substance with a DEA ACSCN of 9210 and a 2014 annual aggregate manufacturing quota of 195 grams, up from 6 grams the year before. The salts in use are the tartrate (free base conversion ratio 0.644) and hydrobromide (0.958).^[7] At the current time^[when?], no levomethorphan pharmaceuticals are marketed in the United States.^{[citation needed]}

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ ^a ^b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springe. pp. 656–. ISBN 978-1-4757-2085-3.
^ Hornback JM (31 January 2005). Organic Chemistry. Cengage Learning. pp. 243–. ISBN 0-534-38951-1.
^ Wainer IW (1996). "Toxicology Through a Looking Glass: Stereochemical Questions and Some Answers". In Wong SH, Sunshine I (eds.). Handbook of Analytical Therapeutic Drug Monitoring and Toxicology. CRC Press. ISBN 9780849326486.
^ ^a ^b ^c Gudin J, Fudin J, Nalamachu S (January 2016). "Levorphanol use: past, present and future". Postgraduate Medicine. 128 (1): 46–53. doi:10.1080/00325481.2016.1128308. PMID 26635068. S2CID 3912175.
^ Bruera ED, Portenoy RK (12 October 2009). Cancer Pain: Assessment and Management. Cambridge University Press. pp. 215–. ISBN 978-0-521-87927-9.
^ "Conversion Factors for Controlled Substances". DEA Diversion Control Division. U.S. Department of Justice, Drug Enforcement Administration (DEA). Archived from the original on 2016-03-02. Retrieved 2014-06-18.

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[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[Elks2014-2] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springe. pp. 656–. ISBN 978-1-4757-2085-3.

[Hornback2005-3] Hornback JM (31 January 2005). Organic Chemistry. Cengage Learning. pp. 243–. ISBN 0-534-38951-1.

[4] Wainer IW (1996). "Toxicology Through a Looking Glass: Stereochemical Questions and Some Answers". In Wong SH, Sunshine I (eds.). Handbook of Analytical Therapeutic Drug Monitoring and Toxicology. CRC Press. ISBN 9780849326486.

[GudinFudin2015-5] Gudin J, Fudin J, Nalamachu S (January 2016). "Levorphanol use: past, present and future". Postgraduate Medicine. 128 (1): 46–53. doi:10.1080/00325481.2016.1128308. PMID 26635068. S2CID 3912175.

[BrueraPortenoy2009-6] Bruera ED, Portenoy RK (12 October 2009). Cancer Pain: Assessment and Management. Cambridge University Press. pp. 215–. ISBN 978-0-521-87927-9.

[7] "Conversion Factors for Controlled Substances". DEA Diversion Control Division. U.S. Department of Justice, Drug Enforcement Administration (DEA). Archived from the original on 2016-03-02. Retrieved 2014-06-18.

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Levomethorphan

See also

References