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Normorphine

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Normorphine
Clinical data
Other namesNormorphine
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • 3,6α-dihydroxy- 4,5α-epoxy- 7,8-didehydromorphinan
CAS Number
PubChem CID
IUPHAR/BPS
CompTox Dashboard (EPA)
ECHA InfoCard100.006.712 Edit this at Wikidata
Chemical and physical data
FormulaC16H17NO3
Molar mass271.311 g/mol g·mol
  (verify)

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

Normorphine has relatively little opioid activity in its own right, 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. It is also produced as a major metabolite of morphine, with its formation from morphine catalysed by the liver enzymes CYP3A4 and CYP2C8.

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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