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Heterocodeine



Heterocodeine
Systematic (IUPAC) name
(5α,6α)-3-hydroxy-6-methoxy-7,8-didehydro-4,5-epoxy-17-methylmorphinan
Identifiers
CAS number 639-47-4
ATC code  ?
PubChem 5462505
Chemical data
Formula C18H21NO3 
Mol. mass 299.364 g/mol
Synonyms Heterocodeine, Morphine 6-methyl ester
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
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Therapeutic considerations
Pregnancy cat.

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Legal status
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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.[1]

Additional recommended knowledge

Heterocodeine is 6 times more potent than morphine[1] due to the masking of the 6-hydroxy group giving greater lipophilicity, in a similar manner to 6-acetylmorphine.[2]


References

  1. ^ Barber RB, Rapoport H. Synthesis of thebaine and oripavine from codeine and morphine. Journal of Medicinal Chemistry. 1975 Nov;18(11):1074-7.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Heterocodeine". A list of authors is available in Wikipedia.
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