Heterocodeine (original) (raw)
Heterocodeine (6-methoxymorphine) is an opiate derivative, the 6-methyl ether of morphine, and a 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. It can be made from morphine by selective methylation. 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.
| Property | Value |
|---|---|
| dbo:abstract | Heterocodeine (6-methoxymorphine) is an opiate derivative, the 6-methyl ether of morphine, and a 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. It can be made from morphine by selective methylation. 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 due to having a substitution at the 6-hydroxy position, in a similar manner to 6-acetylmorphine. 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. 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. (en) |
| dbo:casNumber | 639-47-4 |
| dbo:chEMBL | 358043 |
| dbo:fdaUniiCode | SBO5K94K8L |
| dbo:pubchem | 5462505 |
| dbo:thumbnail | wiki-commons:Special:FilePath/Heterocodeine.svg?width=300 |
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| dbo:wikiPageRevisionID | 1090160978 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Pseudomorphine dbc:4,5-Epoxymorphinans dbc:Ethers dbc:Mu-opioid_receptor_agonists dbc:Phenols dbc:Semisynthetic_opioids dbr:Chemical_structure dbr:Opiate dbr:Codeine dbr:Morphinan dbr:Morphine dbr:Morphine-6-glucuronide dbr:Thebaine dbr:6-Monoacetylmorphine dbr:Isomer dbr:Pholcodine dbr:Methyl dbr:Methyldihydromorphine dbr:Ether |
| dbp:alt | Ball-and-stick model (en) Skeletal formula (en) |
| dbp:atcPrefix | none (en) |
| dbp:c | 18 (xsd:integer) |
| dbp:casNumber | 639 (xsd:integer) |
| dbp:chembl | 358043 (xsd:integer) |
| dbp:chemspiderid | 4575432 (xsd:integer) |
| dbp:h | 21 (xsd:integer) |
| dbp:image | Heterocodeine molecule ball.png (en) |
| dbp:iupacName | -6 (xsd:integer) |
| dbp:legalUs | Schedule II (en) |
| dbp:n | 1 (xsd:integer) |
| dbp:o | 3 (xsd:integer) |
| dbp:pubchem | 5462505 (xsd:integer) |
| dbp:smiles | O[C@H]2\C=C/[C@H]5[C@@H]4NC (en) |
| dbp:stdinchi | 1 (xsd:integer) |
| dbp:stdinchikey | FNAHUZTWOVOCTL-XSSYPUMDSA-N (en) |
| dbp:synonyms | Heterocodeine, Morphine 6-methyl ether (en) |
| dbp:unii | SBO5K94K8L (en) |
| dbp:verifiedfields | changed (en) |
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| dbp:watchedfields | changed (en) |
| dbp:width | 210 (xsd:integer) |
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| dct:subject | dbc:4,5-Epoxymorphinans dbc:Ethers dbc:Mu-opioid_receptor_agonists dbc:Phenols dbc:Semisynthetic_opioids |
| gold:hypernym | dbr:Isomer |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 yago:Abstraction100002137 yago:Chemical114806838 yago:Compound114818238 yago:Element114840755 yago:Material114580897 yago:Matter100020827 yago:OrganicCompound114727670 yago:Part113809207 yago:Phenol114989545 yago:PhysicalEntity100001930 yago:Quintessence114847103 yago:Relation100031921 dbo:ChemicalCompound dbo:Drug yago:Substance100019613 yago:WikicatEthers yago:WikicatPhenols umbel-rc:DrugProduct |
| rdfs:comment | Heterocodeine (6-methoxymorphine) is an opiate derivative, the 6-methyl ether of morphine, and a 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. It can be made from morphine by selective methylation. 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. (en) |
| rdfs:label | Heterocodeine (en) |
| owl:sameAs | freebase:Heterocodeine yago-res:Heterocodeine wikidata:Heterocodeine dbpedia-sh:Heterocodeine dbpedia-sr:Heterocodeine https://global.dbpedia.org/id/4mYuq |
| prov:wasDerivedFrom | wikipedia-en:Heterocodeine?oldid=1090160978&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/Heterocodeine.svg wiki-commons:Special:FilePath/Heterocodeine_molecule_ball.png |
| foaf:isPrimaryTopicOf | wikipedia-en:Heterocodeine |
| is dbo:wikiPageWikiLink of | dbr:List_of_opioids dbr:Codeine dbr:Morphine dbr:Isocodeine dbr:Dihydroisocodeine dbr:C18H21NO3 dbr:Methyldihydromorphine dbr:Opioid |
| is foaf:primaryTopic of | wikipedia-en:Heterocodeine |
