Chemistry:Levomethorphan
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Short description: Opioid analgesic
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| Elimination half-life | 3-6 hours |
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| Formula | C18H25NO |
| Molar mass | 271.404 g·mol−1 |
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Levomethorphan (LVM) (INN, BAN) is an opioid analgesic of the morphinan family that has never been marketed.[1] It is the L-stereoisomer of racemethorphan (methorphan).[1] 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.[2] Levomethorphan is about five times stronger than morphine.[3]
Levomethorphan is a prodrug to levorphanol, analogously to DXM acting as a prodrug to dextrorphan or codeine behaving as a prodrug to morphine.[4] 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.[4] 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.[4] Via activation of the κ-opioid receptor, levomethorphan can produce dysphoria and psychotomimetic effects such as dissociation and hallucinations.[5]
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).[6] At the current time[when?], no levomethorphan pharmaceuticals are marketed in the United States.[citation needed]
See also
- Butorphanol
- Cyclorphan
- Levallorphan
- Levorphanol
- Nalbuphine
- Oxilorphan
- Proxorphan
- Racemorphan
- Xorphanol
References
- ↑ 1.0 1.1 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springe. 14 November 2014. pp. 656–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA656.
- ↑ Organic Chemistry. Cengage Learning. 31 January 2005. pp. 243–. ISBN 0-534-38951-1. https://books.google.com/books?id=FETzRWMGt3YC&pg=PA243.
- ↑ "Toxicology Through a Looking Glass: Stereochemical Questions and Some Answers". Handbook of Analytical Therapeutic Drug Monitoring and Toxicology. CRC Press. 1996. ISBN 9780849326486. https://books.google.com/books?id=3qjUKyL7BokC&pg=PA21.
- ↑ 4.0 4.1 4.2 "Levorphanol use: past, present and future". Postgraduate Medicine 128 (1): 46–53. January 2016. doi:10.1080/00325481.2016.1128308. PMID 26635068.
- ↑ Cancer Pain: Assessment and Management. Cambridge University Press. 12 October 2009. pp. 215–. ISBN 978-0-521-87927-9. https://books.google.com/books?id=2TJ-_oECXM4C&pg=PA215.
- ↑ "Conversion Factors for Controlled Substances". DEA Diversion Control Division. U.S. Department of Justice, Drug Enforcement Administration (DEA). http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html.
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