Phenomorphan

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IUPAC_name = (-)-3-hydroxy-N-(2-phenylethyl)morphinan


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CAS_number = 468-07-5
synonyms = Phenomorphan
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PubChem = 5362458
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C = 24 | H = 29 | N = 1 | O = 1
molecular_weight = 347.493 g/mol
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legal_UK = Class A
legal_US = Schedule I
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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 Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2-thienyl)ethyl) analogues being 60x and 45x stronger than levorphanol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. [Hellerbach J, Schnider O, Besendorf H, Pellmont B. Synthetic Analgesics. Part IIA. Morphinans. Pergamon Press, 1966.]

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