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Normorphine: Wikis

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Normorphine
Systematic (IUPAC) name
3,6α-dihydroxy- 4,5α-epoxy- 7,8-didehydromorphinan
Identifiers
CAS number 466-97-7
ATC code none
PubChem 430245
Chemical data
Formula C 16H17NO3  
Mol. mass 271.311 g/mol
Synonyms Normorphine
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule I (US)
Routes  ?

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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