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
Legal status
Legal status
Identifiers
CAS Number 5666-11-5
ATC code none
PubChem CID 10453145
ChemSpider 8628561 N
UNII 7M86YFN15D YesY
Chemical data
Formula C25H32N2O2
Molar mass 392.534
 NYesY (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.