Levomoramide

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]

Levomoramide

Clinical data
ATC code	none
Legal status
Legal status	AU: S8 (Controlled drug) CA: Schedule I DE: Anlage II (Authorized trade only, not prescriptible) US: Schedule I UN: Narcotic Schedule I
Identifiers
IUPAC name (3R)-3-methyl-4-morpholin-4-yl-2,2-diphenyl-1-pyrrolidin-1-yl-butan-1-one
CAS Number	5666-11-5^N
PubChem CID	10453145
ChemSpider	8628561^N
UNII	7M86YFN15D
ECHA InfoCard	100.024.658
Chemical and physical data
Formula	C25H32N2O2
Molar mass	392.534 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@@H](CN1CCOCC1)C(c1ccccc1)(c1ccccc1)C(=O)N1CCCC1
InChI InChI=1S/C25H32N2O2/c1-21(20-26-16-18-29-19-17-26)25(22-10-4-2-5-11-22,23-12-6-3-7-13-23)24(28)27-14-8-9-15-27/h2-7,10-13,21H,8-9,14-20H2,1H3/t21-/m0/s1^N Key:INUNXTSAACVKJS-NRFANRHFSA-N^N
^NY (what is this?)  (verify)

"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

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.