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Levomoramide
Systematic (IUPAC) name
(3S)-3-methyl-4-morpholin-4-yl-2,2-diphenyl-1-pyrrolidin-1-yl-butan-1-one
Identifiers
CAS number  ?
ATC code none
PubChem 10453145
Chemical data
Formula C 25H32N2O2  
Mol. mass 392.534
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule I (US)
Routes  ?

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 controlled internationally as a Schedule I drug.

References

  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.
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