Levomoramide

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 ;
PubChem CID	10453145;
ChemSpider	8628561 ;
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 ; Key:INUNXTSAACVKJS-NRFANRHFSA-N ;
	(what is this?) (verify)

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 scheduled by UN Single Convention on Narcotic Drugs.

References

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.
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.
Lednicer D (1982). Central Analgetics. p. 194. ISBN 0-471-08314-3.
Janssen PA (1960). Synthetic Analgesics Part 1: Diphenylpropylamines. Pergamon Press. p. 143.

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[1] 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.

[2] 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.

[3] Lednicer D (1982). Central Analgetics. p. 194. ISBN 0-471-08314-3.

[4] Janssen PA (1960). Synthetic Analgesics Part 1: Diphenylpropylamines. Pergamon Press. p. 143.