Phenomorphan

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Phenomorphan
Phenomorphan.svg
Systematic (IUPAC) name
17-(2-Phenylethyl)morphinan-3-ol
Clinical data
Legal status Prohibited (S9) (AU) Class A (UK) Schedule I (US)
Identifiers
CAS number 468-07-5 YesY
ATC code None
PubChem CID 5362458
ChemSpider 16735962 YesY
UNII 26HXE4B73P YesY
Synonyms (-)-3-hydroxy- N- (2-phenylethyl) morphinan
Chemical data
Formula C24H29NO 
Mol. mass 347.493 g/mol
 YesY (what is this?)  (verify)

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 Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings.[2] are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2-thienyl)ethyl) analogues being 60x and 45x stronger than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

References[edit]

  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.