Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Heterocodeine: Difference between pages

{{Short description|Chemical compound}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 461087666

| IUPAC_name = (5α,6α)-6-Methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-3-ol

| alt = Skeletal formula

| width = 210

| image2 = Heterocodeine molecule ball.png

| alt2 = Ball-and-stick model

| legal_US = Schedule II

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| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 639-47-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = SBO5K94K8L

| ChEMBL_Ref = {{ebicite|correct|EBI}}

'''Heterocodeine''' (6-methoxymorphine) is an [[opiate]] derivative, the 6-[[methyl]] [[ether]] of [[morphine]], and a [[chemical structure|structural]] [[isomer]] of [[codeine]]; it is called "hetero-" because it is the reverse isomer of codeine. Heterocodeine was first synthesised in 1932 and first patented in 1935.<ref>{{cite patent | country = US | number = 2058521 }}</ref> It can be made from morphine by selective methylation.<ref name="pmid1177252">{{cite journal | vauthors = Barber RB, Rapoport H | title = Synthesis of thebaine and oripavine from codeine and morphine | journal = Journal of Medicinal Chemistry | volume = 18 | issue = 11 | pages = 1074–7 | date = November 1975 | pmid = 1177252 | doi = 10.1021/jm00245a006 }}</ref> Codeine is the natural mono-methyl ether, but must be metabolized for activity (that is, it is a prodrug). In contrast the semi-synthetic mono-methyl ether, heterocodeine is a direct agonist. The 6,7,8,14 tetradehydro 3,6 methyl di-ether of morphine is [[thebaine]].

Heterocodeine is 6 times more potent than morphine<ref>{{cite web | title = Chemistry of Opioid Analgesics | work = PHA 5155- Neurology Pharmacotherapeutics Medicinal Chemistry Tutorials | vauthors = Woster PM | url = http://www.acsmedchem.org/module/opioid.html | archive-url = https://web.archive.org/web/20070716115228/http://www.acsmedchem.org/module/opioid.html | archive-date=2007-07-16 }}</ref> due to having a substitution at the 6-hydroxy position, in a similar manner to [[6-Monoacetylmorphine|6-acetylmorphine]].<ref>{{cite web | url = http://www.pharmacy.umaryland.edu/faculty/acoop/decfolder/DEC2000.pdf | title = Biological evaluation of compounds for their physical dependence potential & abuse liability. XXIV. | work = Drug evaluation committee of the college on problems of drug dependence | date = 2000 | vauthors = Coop A, Jacobson AE }}</ref> The drug [[methyldihydromorphine]] (dihydroheterocodeine) is a derivative of heterocodeine. Like 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); as well as the 6-acetylmorphine metabolite of heroin this includes heterocodeine.<ref>{{cite journal | vauthors = Brown GP, Yang K, King MA, Rossi GC, Leventhal L, Chang A, Pasternak GW | title = 3-Methoxynaltrexone, a selective heroin/morphine-6beta-glucuronide antagonist | journal = FEBS Letters | volume = 412 | issue = 1 | pages = 35–8 | date = July 1997 | pmid = 9257684 | doi = 10.1016/S0014-5793(97)00710-2 | s2cid = 45475657 | doi-access = free }}</ref>

The relative strength of heterocodeine to codeine has been published as 50, 72, 81, 88, 93, 96, and 108 ×.

It is not mentioned specifically in the Controlled Substances Act 1970 but is a Schedule II controlled substance as an analogue of [[morphinan]] or [[morphine]] under the morphine structure rules of the Analogues Act; in other countries it is usually controlled as a strong opioid.

'''Homocodeine''' is a synonym for [[pholcodine]]. '''Bicodeine''' is a dimer of codeine which is essentially the codeine analogue of [[pseudomorphine]] and is also known as pseudocodeine. It is an occasional component of opium and is also a decomposition product of codeine under certain circumstances.<ref>{{cite web | title = Status Decision of Controlled and Non-Controlled Substances: Codeine dimer | work = Health Canada | date = 15 June 2005 | url = https://isomerdesign.com/Cdsa/HC/StatusDecisions/A-2013-00235%20-%20PDFs/C-Codeine%20dimer%202005-06-16.pdf}}</ref>

== References ==

{{Reflist|2}}

{{Opioidergics}}

[[Category:4,5-Epoxymorphinans]]

[[Category:Ethers]]

[[Category:Mu-opioid receptor agonists]]

[[Category:Phenols]]

[[Category:Semisynthetic opioids]]