Levomethorphan

Levomethorphan
Systematic (IUPAC) name
3-methoxy-17-methylmorphinan
Clinical data
MedlinePlus a682492
Pharmacokinetic data
Half-life 3-6 hours
Identifiers
125-70-2 
None
PubChem CID 5702040
DrugBank DB00514 
ChemSpider 4642423 Yes
UNII 7ZZ22K9QE6 Yes
ChEBI CHEBI:4470 Yes
ChEMBL CHEMBL282713 
Chemical data
Formula C18H25NO
271.397 g/mol
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Levomethorphan is the l-stereoisomer of methorphan. The effects of the two isomers are quite different. Dextromethorphan is an antitussive at low doses and a dissociative at much higher doses, whereas levomethorphan is an opioid analgesic. Levomethorphan has effects similar to levorphanol but is less potent as it must be demethylated to the active form by liver enzymes before becoming active. It can therefore be said to be the codeine analogue of levorphanol.

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 2013 annual aggregate manufacturing quota of 6 grammes. The salts in use are the tartrate (free base conversion ratio 0.64) and hydrobromide (0.77).[1] At the current time, no levomethorphan pharmaceuticals are marketed in the United States.

See also

References