Normorphine
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Normorphine
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|---|---|
| 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 |
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Normorphine is an opiate analogue, the N-demethylated derivative of morphine, that was 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
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