Levomoramide

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Levomoramide
Systematic (IUPAC) name
(3S)-3-methyl-4-morpholin-4-yl-2,2-diphenyl-1-pyrrolidin-1-yl-butan-1-one
Identifiers
CAS number	?
ATC code	?
PubChem	10453145
Chemical data
Formula	C₂₅H₃₂N₂O₂
Mol. mass	392.534
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Schedule I(US)
Routes	?

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

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.^[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 controlled internationally as a Schedule I drug.

References

↑ Janssen PA. Journal of the American Chemical Society. 1956;78:3862.
↑ Janssen PA, Jagenau AM. Journal of Pharmacy and Pharmacology 1957;9:381.
↑ Daniel Lednicer. Central Analgetics. (1982), p194. ISBN 0-471-08314-3
↑ Paul A J Janssen. Synthetic Analgesics Part 1: Diphenylpropylamines. Pergamon Press 1960. p143.

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Opioids (N02A)

Opiate
derivatives

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Opiate metabolites	Codeine-N-Oxide • Morphine-3-glucuronide • Morphine-6-glucuronide • Monoacetylmorphine • Morphine-N-Oxide • Naltrexol • Norcodeine • Normorphine

Morphinans

Aknadinine • Butorphanol • Cyclorphan • Cyprodime • Dextro-3-hydroxy-N-allylmorphinan • Dextromethorphan • Dextrorphan • Dimemorfan • Drotebanol • Levargorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Racemethorphan • Racemorphan • Salutaridine (Sinoacutine) • Sinococuline • Sinomenine (Cocculine)

Benzomorphans

5,9-DEHB • Anazocine • Bremazocine • Cogazocine • Cyclazocine • Dezocine • Eptazocine • Etazocine • Ethylketocyclazocine • Fluorophen • Ketazocine • Metazocine • Pentazocine • Phenazocine • Quadazocine • Thiazocine

4-Phenylpiperidines

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Prodines	Allylprodine • α-meprodine • α-prodine • β-meprodine • β-prodine • Isopromedol • Meprodine • MPPP • PEPAP • Prodine • Prosidol • Trimeperidine (Promedol)
Ketobemidones	Acetoxyketobemidone • Droxypropine • Ketobemidone • Methylketobemidone • Propylketobemidone
Others	Alvimopan • Loperamide • Picenadol

Open Chain
Opioids

Amidones	Dextromethadone • Dipipanone • Hexalgon • Isomethadone • Levomethadone • Methadone • Methadone intermediate • Normethadone • Norpipanone • Phenadoxone (Heptazone) • Pipidone
Methadols	Acetylmethadol • α-methadol • α-acetylmethadol • β-methadol • β-acetylmethadol • Dimepheptanol (Racemethadol) • Levo-α-acetylmethadol • Noracymethadol
Moramides	Dextromoramide • Levomoramide • Moramide intermediate • Racemoramide
Thiambutenes	Thiambutene • Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene • Tipepidine
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Ampromides	Diampromide • Phenampromide • Propiram
Others	IC-26 • Lefetamine • R-4066