Levomoramide

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Levomoramide
Levomoramide.svg
Systematic (IUPAC) name
(3R)-3-methyl-4-morpholin-4-yl-2,2-diphenyl-1-pyrrolidin-1-yl-butan-1-one
Clinical data
Legal status Controlled (S8) (AU) Schedule I (US) Narcotic Schedule I (UN)
Identifiers
ATC code None
PubChem CID 10453145
ChemSpider 8628561 N
UNII 7M86YFN15D YesY
Chemical data
Formula C25H32N2O2 
Mol. mass 392.534
 N (what is this?)  (verify)

Levomoramide is the inactive isomer of the opioid analgesic dextromoramide, invented by the chemist Paul Janssen in 1956. Unlike dextromoramide, which is a potent analgesic with high abuse potential, levomoramide is virtually without activity.[1][2]

"Resolution reveals that the analgetic activity in this case resides almost entirely in the (+) isomer."[3]

"In the α-CH3 series, one of the optical isomers of each enantiomorphic pair is about twice as active as the racemic mixture; the other isomer is devoid of significant analgesic activity."[4]

However, despite being inactive, levomoramide is scheduled by UN Single Convention on Narcotic Drugs.

References[edit]

  1. ^ Janssen PA. Journal of the American Chemical Society. 1956;78:3862.
  2. ^ Janssen PA, Jagenau AM. Journal of Pharmacy and Pharmacology 1957;9:381.
  3. ^ Daniel Lednicer. Central Analgetics. (1982), p194. ISBN 0-471-08314-3
  4. ^ Paul A J Janssen. Synthetic Analgesics Part 1: Diphenylpropylamines. Pergamon Press 1960. p143.