Levomoramide

Drugbox
IUPAC_name = (3S)-3-methyl-4-morpholin-4-yl-2,2-diphenyl-1-pyrrolidin-1-yl-butan-1-one

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PubChem=10453145
smiles = C [C@@H] (CN1CCOCC1)C(c1ccccc1)(c1ccccc1)C(=O)N1CCCC1
DrugBank=
C=25|H=32|N=2|O=2
molecular_weight = 392.534
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legal_US = Schedule I
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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. [Janssen PA. "Journal of the American Chemical Society". 1956;78:3862.] [Janssen PA, Jagenau AM. "Journal of Pharmacy and Pharmacology" 1957;9:381.]

"Resolution reveals that the analgetic activity in this case resides almost entirely in the (+) isomer." [Daniel Lednicer. Central Analgetics. (1982), p194. ISBN 0-471-08314-3]

"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." [Paul A J Janssen. Synthetic Analgesics Part 1: Diphenylpropylamines. Pergamon Press 1960. p143.]

However despite being inactive, levomoramide is controlled internationally as a Schedule I drug.

References