Phenomorphan

Phenomorphan

Clinical data
Other names	(-)-3-hydroxy- N- (2-phenylethyl) morphinan
ATC code	none
Legal status
Legal status	UK: Class A US: Schedule I
Identifiers
IUPAC name 17-(2-phenylethyl)morphinan-3-ol
CAS Number	468-07-5
PubChem CID	5362458
ChemSpider	16735962 Y
UNII	26HXE4B73P
CompTox Dashboard (EPA)	DTXSID70878657
ECHA InfoCard	100.006.732
Chemical and physical data
Formula	C24H29NO
Molar mass	347.493 g/mol g·mol−1
3D model (JSmol)	Interactive image
SMILES Oc3ccc4C[C@H]1N(CC[C@@]2(CCCC[C@@H]12)c4c3)CCc5ccccc5
InChI InChI=1S/C24H29NO/c26-20-10-9-19-16-23-21-8-4-5-12-24(21,22(19)17-20)13-15-25(23)14-11-18-6-2-1-3-7-18/h1-3,6-7,9-10,17,21,23,26H,4-5,8,11-16H2/t21-,23+,24+/m0/s1 Y Key:CFBQYWXPZVQQTN-QPTUXGOLSA-N Y
NY (what is this?)  (verify)

Phenomorphan 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 Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2-thienyl)ethyl) analogues being 60x and 45x stronger than levorphanol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.

See also

• 14-Cinnamoyloxycodeinone
• 14-Phenylpropoxymetopon
• 7-PET
• N-Phenethylnormorphine
• N-Phenethyl-14-ethoxymetopon
• RAM-378
• Ro4-1539