Heterocodeine
| 200px | |
| Systematic (IUPAC) name | |
|---|---|
|
(5α,6α)-6-methoxy- 17-methyl- 7,8-didehydro- 4,5-epoxymorphinan- 3-ol | |
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| Legal status |
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| Identifiers | |
| CAS Number | 639-47-4 |
| ATC code | none |
| PubChem | CID 5462505 |
| Synonyms | Heterocodeine, Morphine 6-methyl ether |
| Chemical data | |
| Formula | C18H21NO3 |
| Molar mass | 299.364 g/mol[[Script error: No such module "String".]] |
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] Codeine is the natural mono-methyl ester, so methylated where it must be metabolized to activate, and thus acting as a prodrug. Functionality contrasting this 6-position (semi-)synthetic mono-methyl ester, heterocodeine, which is a direct agonist: named "hetero-" for being the isomeric reverse oriented partner to codeine.
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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- ↑ 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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