Levomethorphan

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Not to be confused with Dextromethorphan, Dextrorphan, or 3-Methoxymorphinan.
Levomethorphan
Clinical data
Dependence
liability		High
Addiction
liability		High
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Elimination half-life3-6 hours
Identifiers
  • (1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.320 Edit this at Wikidata
Chemical and physical data
FormulaC18H25NO
Molar mass271.404 g·mol−1
3D model (JSmol)
  • COc1ccc2C[C@@H]3[C@@H]4CCCC[C@]4(CCN3C)c2c1
  • 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 checkY
  • Key:MKXZASYAUGDDCJ-CGTJXYLNSA-N checkY
 ☒NcheckY (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]

See also

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References

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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.
  2. ^ 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.
  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.
  5. ^ 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.
  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.