Heterocodeine
| 200px | |
| Systematic (IUPAC) name | |
|---|---|
|
(5α,6α)-6-methoxy- 17-methyl- 7,8-didehydro- 4,5-epoxymorphinan- 3-ol | |
| Legal status | |
| Legal status |
|
| 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.
References
Cite error: Invalid <references> tag;
parameter "group" is allowed only.
<references />, or <references group="..." />
| 40px | This analgesic-related article is a stub. You can help ssf by expanding it. |
- Jump up ↑ http://www.pharmacy.umaryland.edu/faculty/acoop/decfolder/DEC2000.pdf
- Jump up ↑ Barber RB, Rapoport H. Synthesis of thebaine and oripavine from codeine and morphine. Journal of Medicinal Chemistry. 1975 Nov;18(11):1074-7.
- Jump up ↑ Chemistry of Opioid Analgesics - Neurology Pharmacotherapeutics, Wilson and Gisvold, pgs. 629-656.
- Jump up ↑ 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
- Pages with script errors
- Pages with broken file links
- Drugs with non-standard legal status
- Infobox drug tracked parameters
- Articles without EBI source
- Chemical pages without ChemSpiderID
- Chemical pages without DrugBank identifier
- Articles without KEGG source
- Articles without InChI source
- Articles without UNII source
- Drugs not assigned an ATC code
- Articles containing unverified chemical infoboxes
- Opioids
- Morphinans
- Phenols
- Ethers
- Analgesic stubs
- 2Fix
