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	?

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.

[edit] 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.

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