Levomoramide

Levomoramide

Legal status
Legal status	US: Schedule I
Identifiers
IUPAC name (3S)-3-methyl-4-morpholin-4-yl-2,2-diphenyl-1-pyrrolidin-1-yl-butan-1-one
PubChem CID	10453145
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C25H32N2O2
Molar mass	392.534
3D model (JSmol)	Interactive image
SMILES C[C@@H](CN1CCOCC1)C(c1ccccc1)(c1ccccc1)C(=O)N1CCCC1

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

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Overview

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.

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

"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."

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