Levomethorphan

Not to be confused with Dextromethorphan, Dextrorphan, or 3-Methoxymorphinan.

Levomethorphan

Systematic (IUPAC) name
3-methoxy-17-methylmorphinan
Clinical data
MedlinePlus	a682492
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) US: Schedule II
Pharmacokinetic data
Biological half-life	3-6 hours
Identifiers
CAS Number	125-70-2 N
ATC code	None
PubChem	CID: 5702040
DrugBank	DB00514 N
ChemSpider	4642423 Y
UNII	7ZZ22K9QE6 Y
ChEBI	CHEBI:4470 Y
ChEMBL	CHEMBL282713 N
Chemical data
Formula	C18H25NO
Molecular mass	271.397 g/mol
SMILES CN1CC[C@]23CCCC[C@H]2[C@H]1Cc4c3cc(cc4)OC
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 (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 the racemethorphan are quite different, with dextromethorphan (DXM) contrarily being an antitussive at low doses and a dissociative hallucinogen at much higher doses.

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 KOR, 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 2014 annual aggregate manufacturing quota of 195 grammes, up from 6 grammes 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

• Butorphanol
• Cyclorphan
• Levallorphan
• Levorphanol
• Nalbuphine
• Oxilorphan
• Proxorphan
• Racemorphan
• Xorphanol