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)
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class A
  • US: Schedule I
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.006.732
Chemical and physical data
FormulaC24H29NO
Molar mass347.493 g/mol g·mol−1
3D model (JSmol)
  (verify)

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 Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings.[2] are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2-thienyl)ethyl) analogues being 60x and 45x stronger than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

References
  1. 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
  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.


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