Phenomorphan
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| Systematic (IUPAC) name | |
| 17-(2-Phenylethyl)morphinan-3-ol | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Prohibited (S9) (AU) Class A (UK) Schedule I (US) |
| Identifiers | |
| CAS number | 468-07-5  |
| ATC code | None |
| PubChem | CID 5362458 |
| ChemSpider | 16735962 |
| UNII | 26HXE4B73P |
| Synonyms | (-)-3-hydroxy- N- (2-phenylethyl) morphinan |
| Chemical data | |
| Formula | C24H29NO |
| Mol. mass | 347.493 g/mol |
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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 Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings.[2] are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2-thienyl)ethyl) analogues being 60x and 45x stronger than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 [edit]
- 14-Cinnamoyloxycodeinone
- 14-Phenylpropoxymetopon
- 7-PET
- N-Phenethylnormorphine
- N-Phenethylnordesomorphine
- N-Phenethyl-14-ethoxymetopon
- RAM-378
- Ro4-1539
References [edit]
- ^ US patent 2885401, Andre Grussner, Joseph Hellerbach, Otto Schnider, "Process for making morphinan derivatives and products available thereby", published 1956-03-22, issued 1959-05-05
- ^ US patent 2970147, Andre Grussner, Joseph Hellerbach, Otto Schnider, "3-hydroxy-N-(heterocyclic-ethyl)-morphinans", published 1958-11-26, issued 1961-01-31
- ^ Hellerbach J., Schnider O, Besendorf H, Pellmont B (1966). Synthetic Analgesics: Part IIA. Morphinans. International series of monographs on organic chemistry. Pergamon Press.
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