- Normorphine
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Normorphine 
Systematic (IUPAC) name 3,6α-dihydroxy- 4,5α-epoxy- 7,8-didehydromorphinan Clinical data Pregnancy cat. ? Legal status Schedule I (US) Identifiers CAS number 466-97-7 
ATC code None PubChem CID 430245 IUPHAR ligand 1630 UNII XUI1Y24IMI 
Synonyms Normorphine Chemical data Formula C16H17NO3 Mol. mass 271.311 g/mol 
(what is this?) (verify)Normorphine is an opiate analogue that is derived from the N-demethylated derivative of morphine first described in the 1950s[1] when a large group of N-substituted morphine analogues were characterized for activity.
Normorphine has relatively little opioid activity in its own right,[2][3] 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.[4] It is also produced as a major metabolite of morphine,[5] with its formation from morphine catalysed by the liver enzymes CYP3A4 and CYP2C8.[6]
References
- ^ Journal of the American Chemistry Society 75,4963 (1953)
- ^ 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
- ^ 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
- ^ Daniel Lednicer. Central Analgetics. (1982), p146. ISBN 0-471-08314-3
- ^ 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
- ^ 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
Categories:- Opiates
- Morphinans
- Phenols
- Alcohols
- Opioid metabolites
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