Chemistry:Phenomorphan
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Short description: Chemical compound
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| Other names | (-)-3-hydroxy- N- (2-phenylethyl) morphinan |
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| Formula | C24H29NO |
| Molar mass | 347.502 g·mol−1 |
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Phenomorphan[1] is an opioid analgesic. It is not currently used in medicine, but has similar side-effects to other opiates, which include itching, nausea and respiratory depression.
Phenomorphan is a highly potent drug due to the N-phenethyl group, which boosts affinity to the μ-opioid receptor, and so phenomorphan is around 10x more potent than levorphanol, which is itself 6-8x the potency of morphine. Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings[2] are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2-thienyl)ethyl) analogues being 60x and 45x stronger than levorphanol, respectively.[3]
See also
- 14-Cinnamoyloxycodeinone
- 14-Phenylpropoxymetopon
- 7-PET
- N-Phenethylnormorphine
- N-Phenethylnordesomorphine
- N-Phenethyl-14-ethoxymetopon
- RAM-378
- Ro4-1539
References
- ↑ Grussner A, Hellerbach J, Schnider O, "Process for making morphinan derivatives and products available thereby", US patent 2885401, published 1956-03-22, issued 1959-05-05
- ↑ Andre Grussner, Joseph Hellerbach, Otto Schnider, "3-hydroxy-N-(heterocyclic-ethyl)-morphinans", US patent 2970147, published 1958-11-26, issued 1961-01-31
- ↑ Synthetic Analgesics: Part IIA. Morphinans. International series of monographs on organic chemistry. Pergamon Press. 1966. https://www.scribd.com/doc/39966259/Synthetic-Analgesics-1966-Part-IIA-Morphinans.
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