Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Heterocodeine: Difference between pages
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Saving copy of the {{drugbox}} taken from revid 461020360 of page Heterocodeine for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number'). |
Entranced98 (talk | contribs) Importing Wikidata short description: "Chemical compound" |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Heterocodeine|oldid=461020360}} 461020360] of page [[Heterocodeine]] with values updated to verified values.}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| image = Heterocodeine.svg |
| image = Heterocodeine.svg |
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| alt = Skeletal formula |
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| width = |
| width = 210 |
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| image2 = Heterocodeine molecule ball.png |
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| alt2 = Ball-and-stick model |
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<!--Clinical data--> |
<!--Clinical data--> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = |
| legal_US = Schedule II |
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| legal_status = |
| legal_status = |
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| routes_of_administration = |
| routes_of_administration = |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| CAS_number_Ref = {{cascite| |
| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = |
| CAS_number = 639-47-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = SBO5K94K8L |
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| ATC_prefix = none |
| ATC_prefix = none |
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| ATC_suffix = |
| ATC_suffix = |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 358043 |
| ChEMBL = 358043 |
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| PubChem = 5462505 |
| PubChem = 5462505 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=18 | H=21 | N=1 | O=3 |
| C=18 | H=21 | N=1 | O=3 |
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| molecular_weight = 299.364 g/mol |
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| 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 |
| 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 |
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| InChI = 1/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 |
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| InChIKey = FNAHUZTWOVOCTL-XSSYPUMDBX |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
| StdInChI = 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 |
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| synonyms = Heterocodeine, Morphine 6-methyl ether |
| synonyms = Heterocodeine, Morphine 6-methyl ether |
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'''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]]. |
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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> |
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The relative strength of heterocodeine to codeine has been published as 50, 72, 81, 88, 93, 96, and 108 ×. |
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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. |
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'''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> |
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== References == |
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{{Reflist|2}} |
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{{Opioidergics}} |
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[[Category:4,5-Epoxymorphinans]] |
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[[Category:Ethers]] |
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[[Category:Mu-opioid receptor agonists]] |
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[[Category:Phenols]] |
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[[Category:Semisynthetic opioids]] |