Chemistry:Normorphine
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| Other names | Normorphine |
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| Formula | C16H17NO3 |
| Molar mass | 271.316 g·mol−1 |
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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. The compound 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] with its formation from morphine catalyzed by the liver enzymes CYP3A4 and CYP2C8.[5]
Normorphine is a controlled substance listed under the Single Convention On Narcotic Drugs 1961 and the laws in various states implementing it; for example, in the United States it is a Schedule I Narcotic controlled substance, with an ACSCN of 9313 and an annual aggregate manufacturing quota of 18 grams in 2014, unchanged from the prior year. The salts in use are the free base hexahydrate (free base conversion ratio 0.715), and hydrochloride (0.833).[6]
References
- ↑ "N-Substituted epoxymorphinans". Journal of the American Chemical Society 75 (20): 4963–7. October 1953. doi:10.1021/ja01116a024.
- ↑ "Human pharmacology and addiction liability of normorphine". The Journal of Pharmacology and Experimental Therapeutics 122 (3): 359–69. March 1958. PMID 13539761.
- ↑ "Analgesic potency of normorphine in patients with postoperative pain". The Journal of Pharmacology and Experimental Therapeutics 124 (3): 260–3. November 1958. PMID 13588540.
- ↑ "Urinary excretion of morphine and its metabolites in morphine-dependent subjects". The Journal of Pharmacology and Experimental Therapeutics 192 (1): 201–10. January 1975. PMID 235634.
- ↑ "Identification of CYP3A4 and CYP2C8 as the major cytochrome P450 s responsible for morphine N-demethylation in human liver microsomes". Xenobiotica; the Fate of Foreign Compounds in Biological Systems 33 (8): 841–54. August 2003. doi:10.1080/0049825031000121608. PMID 12936704.
- ↑ "Quotas - 2014". DEA Diversion Control Division. http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm.
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