Heterocodeine: Difference between revisions

Heterocodeine
Clinical data
Other names	Heterocodeine, Morphine 6-methyl ether
ATC code	none;
Legal status
Legal status	US: CII (US);
Identifiers
	IUPAC name (5α,6α)-6-methoxy- 17-methyl- 7,8-didehydro- 4,5-epoxymorphinan- 3-ol;
CAS Number	639-47-4 ;
PubChem CID	5462505;
ChemSpider	4575432 ;
ChEMBL	ChEMBL358043 ;
CompTox Dashboard (EPA)	DTXSID40905126 ;
ECHA InfoCard	100.010.325
Chemical and physical data
Formula	C18H21NO3
Molar mass	299.364 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(C)[C@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(O)ccc3C4)C;
	InChI InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-6-14(21-2)17(18)22-16-13(20)5-3-10(15(16)18)9-12(11)19/h3-6,11-12,14,17,20H,7-9H2,1-2H3/t11-,12+,14-,17-,18-/m0/s1 ; Key:FNAHUZTWOVOCTL-XSSYPUMDSA-N ;
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Revision as of 19:52, 19 October 2012

Heterocodeine (6-methoxymorphine) is an opiate derivative, the 6-methyl ether of morphine, and a structural isomer of codeine. Heterocodeine was first synthesised in 1932 and was first patented in 1935.^[1] It can be made from morphine by selective methylation.^[2] Codeine is the natural mono-methyl ether, so methylated where it must be metabolized to activate, and thus acting as a prodrug. Functionality contrasting this 6-position (semi-)synthetic mono-methyl ether, 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. As noted about the morphine metabolite morphine-6-glucuronide, 6-position branches (esters or ethers) of morphine bind to the otherwise unagonized human mu receptor subtype mu-3 (or μ3), this includes, beside the 6-acetylmorphine metabolite of heroin, heterocodeine.^[5]

References

^ US Patent 2058521
^ 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
^ Brown GP, Yang K, King MA; et al. (1997). "3-Methoxynaltrexone, a selective heroin/morphine-6beta-glucuronide antagonist". FEBS Lett. 412 (1): 35–8. doi:10.1016/S0014-5793(97)00710-2. PMID 9257684. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

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[1] US Patent 2058521

[2] Barber RB, Rapoport H. Synthesis of thebaine and oripavine from codeine and morphine. Journal of Medicinal Chemistry. 1975 Nov;18(11):1074-7.

[3] Chemistry of Opioid Analgesics - Neurology Pharmacotherapeutics, Wilson and Gisvold, pgs. 629-656.

[4] 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

[5] Brown GP, Yang K, King MA; et al. (1997). "3-Methoxynaltrexone, a selective heroin/morphine-6beta-glucuronide antagonist". FEBS Lett. 412 (1): 35–8. doi:10.1016/S0014-5793(97)00710-2. PMID 9257684. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

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 == References ==
 {{reflist}}
+{{Opioids}}
+[[Category:Opioids]]
 [[Category:Morphinans]]