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Mu-opioid receptor agonists
Levomethorphan
Другие языки:

Levomethorphan

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Not to be confused with Dextromethorphan, Dextrorphan, or 3-Methoxymorphinan.
Levomethorphan
Levomethorphan.svg
Levometorfan.png
Clinical data
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 3-6 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
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.320
Chemical and physical data
Formula C18H25NO
Molar mass 271.404 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. It is the L-stereoisomer of racemethorphan (methorphan). 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. Levomethorphan is about five times stronger than morphine.

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

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

See also


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