Heterocodeine

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IUPAC_name = (5α,6α)-3-hydroxy-6-methoxy-7,8-didehydro-4,5-epoxy-17-methylmorphinan


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CAS_number = 639-47-4
synonyms = Heterocodeine, Morphine 6-methyl ether
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PubChem = 5462505
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C = 18 | H = 21 | N = 1 | O = 3
molecular_weight = 299.364 g/mol
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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, and can be made from morphine by selective methylation. [Barber RB, Rapoport H. Synthesis of thebaine and oripavine from codeine and morphine. "Journal of Medicinal Chemistry". 1975 Nov;18(11):1074-7.]

Heterocodeine is 6 times more potent than morphine [http://www.acsmedchem.org/module/opioid.html] due to having a substitution at the 6-hydroxy position, in a similar manner to 6-acetylmorphine. [http://www.pharmacy.umaryland.edu/faculty/acoop/decfolder/DEC2000.pdf]

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