Phenomorphan

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

Clinical data
Other names	(-)-3-hydroxy- N- (2-phenylethyl) morphinan
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) CA: Schedule I DE: Anlage I (Authorized scientific use only) 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
UNII	26HXE4B73P
CompTox Dashboard (EPA)	DTXSID70878657
ECHA InfoCard	100.006.732
Chemical and physical data
Formula	C24H29NO
Molar mass	347.502 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 Key:CFBQYWXPZVQQTN-QPTUXGOLSA-N
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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 Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings.[2] are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2-thienyl)ethyl) analogues being 60x and 45x stronger than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

1. US patent 2885401, Grussner A, Hellerbach J, Schnider O, "Process for making morphinan derivatives and products available thereby", published 1956-03-22, issued 1959-05-05
2. US patent 2970147, Andre Grussner, Joseph Hellerbach, Otto Schnider, "3-hydroxy-N-(heterocyclic-ethyl)-morphinans", published 1958-11-26, issued 1961-01-31
3. Hellerbach J, Schnider O, Besendorf H, Pellmont B (1966). Synthetic Analgesics: Part IIA. Morphinans. International series of monographs on organic chemistry. Pergamon Press.