Levomethorphan

Levomethorphan (LVM) (INN, BAN) is an opioid analgesic of the morphinan family that has never been marketed.[1] It is the L-stereoisomer of racemethorphan (methorphan).[1] The effects of the two isomers of the racemethorphan are quite different, with dextromethorphan (DXM) being an antitussive at low doses and a dissociative hallucinogen at much higher doses.[2] Levomethorphan is about five times stronger than morphine. [3]

Not to be confused with Dextromethorphan, Dextrorphan, or 3-Methoxymorphinan.
Levomethorphan
Clinical data
ATC code
  • None
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class A
  • US: Schedule II
Pharmacokinetic data
Elimination half-life3-6 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
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.320
Chemical and physical data
FormulaC18H25NO
Molar mass271.404 g·mol−1
3D model (JSmol)
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 Y
  • Key:MKXZASYAUGDDCJ-CGTJXYLNSA-N Y
 NY (what is this?)  (verify)

Levomethorphan is a prodrug to levorphanol, analogously to DXM acting as a prodrug to dextrorphan or codeine behaving as a prodrug to morphine.[4] 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.[4] 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.[4] Via activation of the kappa opioid receptor, levomethorphan can produce dysphoria and psychotomimetic effects such as dissociation and hallucinations.[5]

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).[6] At the current time, no levomethorphan pharmaceuticals are marketed in the United States.

See also

References
  1. 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.
  2. Hornback JM (31 January 2005). Organic Chemistry. Cengage Learning. pp. 243–. ISBN 0-534-38951-1.
  3. 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.
  4. 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.
  5. Bruera ED, Portenoy RK (12 October 2009). Cancer Pain: Assessment and Management. Cambridge University Press. pp. 215–. ISBN 978-0-521-87927-9.
  6. "Conversion Factors for Controlled Substances". DEA Diversion Control Division. U.S. Department Of Justice, Drug Enforcement Administration (DEA).
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