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Opioid analgesic From Wikipedia, the free encyclopedia
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]
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| Dependence liability | High |
| Addiction liability | High |
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| Elimination half-life | 3-6 hours |
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| ECHA InfoCard | 100.004.320 |
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| Formula | C18H25NO |
| Molar mass | 271.404 g·mol−1 |
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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]
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