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.^[2][3]

Levomoramide

Clinical data
ATC code	none
Legal status
Legal status	AU: S8 (Controlled drug) BR: Class A1 (Narcotic drugs)[1] 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
KEGG	D12695 Y
CompTox Dashboard (EPA)	DTXSID401016989
ECHA InfoCard	100.024.658
Chemical and physical data
Formula	C25H32N2O2
Molar mass	392.543 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."^[4]

"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."^[5]

However, despite being inactive, levomoramide is scheduled by UN Single Convention on Narcotic Drugs.

References

1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
2. Janssen PA, Janseen JC (August 1956). "A new series of potent analgesics". Journal of the American Chemical Society. 78 (15): 3862. doi:10.1021/ja01596a087.
3. Janssen PA, Jageneau AH (September 1957). "A new series of potent analgesics". Journal of Pharmacy and Pharmacology. 9 (1): 381–400. doi:10.1111/j.2042-7158.1957.tb12290.x. S2CID 58956931.
4. Lednicer D (1982). Central Analgetics. Wiley. p. 194. ISBN 0-471-08314-3.
5. Janssen PA (1960). Synthetic Analgesics Part 1: Diphenylpropylamines. Pergamon Press. p. 143.