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Heterocodeine
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| Systematic (IUPAC) name | |
| (5α,6α)-6-methoxy- 17-methyl- 7,8-didehydro- 4,5-epoxymorphinan- 3-ol | |
| Identifiers | |
| CAS number | 639-47-4 |
| ATC code | none |
| PubChem | 5462505 |
| Chemical data | |
| Formula | C18H21NO3 |
| Mol. mass | 299.364 g/mol |
| Synonyms | Heterocodeine, Morphine 6-methyl ether |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status |
?(US) |
| Routes | ?
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Heterocodeine (6-methylmorphine) is an opiate derivative, the 6-methyl ether of morphine, and a structural isomer of codeine. Heterocodeine was first synthesised in 1932,[1] and can be made from morphine by selective methylation.[2]
Heterocodeine is 6 times more potent than morphine[3] due to having a substitution at the 6-hydroxy position, in a similar manner to 6-acetylmorphine.[4] The drug methyldihydromorphine (dihydroheterocodeine) is a derivative of heterocodeine.
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References
- ^ http://www.pharmacy.umaryland.edu/faculty/acoop/decfolder/DEC2000.pdf
- ^ Barber RB, Rapoport H. Synthesis of thebaine and oripavine from codeine and morphine. Journal of Medicinal Chemistry. 1975 Nov;18(11):1074-7.
- ^ Chemistry of Opioid Analgesics - Neurology Pharmacotherapeutics, Wilson and Gisvold, pgs. 629-656.
- ^ Biological evaluation of compounds for their physical dependence potential & abuse liability. XXIV. Drug evaluation committee of the college on problems of drug dependence (2000) A. Coop (Biological Coordinator, DEC, CPDD), & A. E. Jacobson
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