Normorphine

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Normorphine
Normorphine.svg
Clinical data
SynonymsNormorphine
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
E number{{#property:P628}}
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Chemical and physical data
FormulaC16H17NO3
Molar mass271.311 g/mol

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


Overview

Normorphine is an opiate analogue that is the N-demethylated derivative of morphine.

Normorphine has relatively little opioid activity in its own right,[1][2] but is a useful intermediate which can be used to produce both opioid antagonists such as nalorphine, and also potent opioid agonists such as N-phenethylnormorphine.[3] It is also produced as a major metabolite of morphine,[4] with its formation from morphine catalysed by the liver enzymes CYP3A4 and CYP2C8.[5]

References

  1. Fraser HF, Wikler A, Van Horn GD, Eisenman AJ, Isbell H. Human pharmacology and addiction liability of normorphine. Journal of Pharmacology and Experimental Therapeutics. 1958 Mar;122(3):359-69. PMID 13539761
  2. Lasagna L, De Kornfeld TJ. Analgesic potency of normorphine in patients with postoperative pain. Journal of Pharmacology and Experimental Therapeutics. 1958 Nov;124(3):260-3. PMID 13588540
  3. Daniel Lednicer. Central Analgetics. (1982), p146. ISBN 0-471-08314-3
  4. Yeh SY. Urinary excretion of morphine and its metabolites in morphine-dependent subjects. Journal of Pharmacology and Experimental Therapeutics. 1975 Jan;192(1):201-10. PMID 235634
  5. Projean D, Morin PE, Tu TM, Ducharme J. Identification of CYP3A4 and CYP2C8 as the major cytochrome P450 s responsible for morphine N-demethylation in human liver microsomes. Xenobiotica. 2003 Aug;33(8):841-54. PMID 12936704

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