Clinical data | |
---|---|
Other names | (-)-3-hydroxy- N- (2-phenylethyl) morphinan |
ATC code |
|
Legal status | |
Legal status |
|
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
KEGG | |
CompTox Dashboard ( EPA) | |
ECHA InfoCard | 100.006.732 |
Chemical and physical data | |
Formula | C24H29NO |
Molar mass | 347.502 g·mol−1 |
3D model ( JSmol) | |
| |
| |
(verify) |
Phenomorphan [2] 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 Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings [3] are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2- thienyl)ethyl) analogues being 60x and 45x stronger than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. [4]
Clinical data | |
---|---|
Other names | (-)-3-hydroxy- N- (2-phenylethyl) morphinan |
ATC code |
|
Legal status | |
Legal status |
|
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
KEGG | |
CompTox Dashboard ( EPA) | |
ECHA InfoCard | 100.006.732 |
Chemical and physical data | |
Formula | C24H29NO |
Molar mass | 347.502 g·mol−1 |
3D model ( JSmol) | |
| |
| |
(verify) |
Phenomorphan [2] 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 Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings [3] are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2- thienyl)ethyl) analogues being 60x and 45x stronger than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. [4]