Phenomorphan
 | |
| Systematic (IUPAC) name | |
|---|---|
| 17-(2-Phenylethyl)morphinan-3-ol | |
| Clinical data | |
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| Identifiers | |
468-07-5  | |
| None | |
| PubChem | CID 5362458 |
| ChemSpider |
16735962 |
| UNII |
26HXE4B73P |
| Synonyms | (-)-3-hydroxy- N- (2-phenylethyl) morphinan |
| Chemical data | |
| Formula | C24H29NO |
| 347.493 g/mol | |
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SMILES
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| (what is this?) (verify) | |
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 Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings.[2] are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2-thienyl)ethyl) analogues being 60x and 45x stronger than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
- ↑ 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.