ATC code None CAS Number 125-70-2 ChemSpider 4642423 | Biological half-life 3-6 hours PubChem CID 5362449 Molar mass 271.397 g/mol | |
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Legal status AU: S9 (Prohibited)CA: Schedule IDE: Anlage I (Controlled)UK: Class AUS: Schedule II |
Levomethorphan meaning
Levomethorphan (INN, BAN) is an opioid analgesic of the morphinan family that has never been marketed. It is the -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. It is about five times stronger than morphine.
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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. 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.