Heterocodeine

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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	C₁₈H₂₁N O₃
Mol. mass	299.364 g/mol
Synonyms	Heterocodeine, Morphine 6-methyl ether
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

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]

Heterocodeine is 6 times more potent than morphine[1] due to having a substitution at the 6-hydroxy position, in a similar manner to 6-acetylmorphine.[2]

This pharmacology-related article is a stub. You can help Wikipedia by expanding it.

References

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

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Opioids (N02A)

Opium
derivatives

Whole Opium
Preparations

Diascordium • Dover's powder • Granulated Opium • Laudanum • Mithridate • Opium • Paregoric • Poppy Straw Concentrate • Poppy tea • Powdered Opium • Raw Opium • Smoking Opium • Theriac

Natural Opiates

Opium Alkaloids see also: Components of Opium	16-Hydroxythebaine • Allocryptopine • Berberine • Bulbocapnine • Canadine • Codamine • Codeine • Coptisine • Coreximine • Corytuberine • Cotarnine • Cryptopine • Cycloartenol • Cycloartenone • Cyclolaudenol • Dehydroreticuline • Dihydrosanguinarine • Eupaverine • Glaucine • Hydrocotarnine • Isoboldine • Isocorypalmine • Laudanidine • Laudanine • Laudanosine • Magnoflorine • Morphine • Narceine • Narceinone • Narcotoline • Neopine • Norlaudanosoline • Norsanguinarine • Noscapine • Oripavine • Oxysanguinarine • Palaudine • Papaverine • Papaveraldine • Papaverrubine B (O-Methyl-Porphyroxine) • Papaverrubine C (Epiporphyroxine) • Papaverrubine D (Porphyroxine) • Perparin • Pseudomorphine • Reticuline • Salutaridine (Sinoacutine) • Sanguinarine • Scoulerine • Somniferine • Stepholidine • Thebaine

Alkaloid Salts Mixtures	Omnopon • Pantopon • Papaveretum • Tetrapon

Semisynthetics

Morphine Family	14-hydroxydihydromorphine (Hydromorphinol) • 2,4-Dinitrophenylmorphine • 6-Methyldihydromorphine • 6-Methylenedihydrodesoxymorphine • Apomorphine • Desomorphine • Diacetyldihydromorphine • Dihydrodesoxymorphine • Dihydroheroin • Dihydromorphine • Dipropanoylmorphine • Ethyldihydromorphine • Heroin (Diamorphine) • Heroin-7,8-Oxide • Methyldesorphine • Methyldihydromorphine • Nicomorphine • N-Phenethylnormorphine

Codeine-Dionine Family	Acetylcodeine • Benzylmorphine • Codeine • Desocodeine • Dihydroheterocodeine • Ethylmorphine (Dionine) • Heterocodeine • Isocodeine • Morpholinylethylmorphine (Pholcodine) • Myrophine • Nalodeine • Transisocodeine

Morphinones	14-Ethoxymetopon • 14-Methoxymetopon • 14-O-Methyloxymorphone • 14-Phenylpropoxymetopon • 14-Hydroxydihydromorphinone (Oxymorphone) • 7-Spiroindanyloxymorphone • 8,14-Dihydroxydihydromorphinone • Acetylmorphone • Ethyldihydromorphinone • Hydromorphinol • Hydromorphinone • Hydromorphone • Hydroxycodeine • Methyldihydromorphinone • Metopon • Morphinol • Morphinone • N-Phenethyl-14-ethoxymetopon • Oxymorphone • Pentamorphone • Semorphone

Codeinones	1-carboxy-14-hydroxydihydrocodeinone • 1-carbethoxy-14-hydroxydihydrocodeinone • 14-Hydroxydihydrocodeinone (Oxycodone) • Acetyldihydrocodeinone • Codeinone • Codorphone • Codoxime • Dihydrocodeinone enol acetate • Dihydrohydroxycodeinone • Hydrocodone • Oxycodone • Thebacon

Dihydrocodeine Series	14-hydroxydihydrocodeine • Acetyldihydrocodeine • Dihydrocodeine • Dihydrodesoxycodeine/Desocodeine • Dihydroisocodeine • Nicocodeine • Nicodicodeine

Nitrogen Morphine Derivatives	Codeine-N-Oxide • Heroin-N-Oxide • Hydromorphone-N-Oxide • Morphine-N-Oxide

Others	α-chlorocodide • Azidomorphine • Chloromorphide • Hydromorphazone • Morphazone • Oxymorphazone • Pholcodine

Active Opiate
Metabolites

Codeine-N-Oxide (Genocodeine) • Hydromorphone-N-Oxide • Heroin-7,8-Oxide • Morphine-3-glucuronide • Morphine-6-glucuronide • Monoacetylmorphine • Morphine-N-Oxide (Genomorphine) • Naltrexol • Norcodeine • Normorphine

Morphinans

Morphinan Series	4-chlorophenylpyridomorphinan • Cyclorphan • Dextro-3-hydroxy-N-allylmorphinan • Dextromethorphan • Dextrorphan • Dimemorfan • Levargorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • N-Methylmorphinan • Oxilorphan • Phenomorphan • Racemethorphan • Racemorphan • Stephodeline • Xorphanol

Others	1-Nitroaknadinine • 14-episinomenine • 5,6-Dihydronorsalutaridine • 6-Ketonalbuphine • Aknadinine • Butorphanol • Cephakicine • Cephasamine • Cyprodime • Drotebanol • Fenfangjine G • Nalbuphine • Sinococuline • Sinomenine (Cocculine) • Tannagine

Benzomorphans

5,9-DEHB • Allylnormetazocine • Anazocine • Bremazocine • Cogazocine • Cyclazocine • Dezocine • Eptazocine • Etazocine • Ethylketocyclazocine • Fluorophen • Ketazocine • Metazocine • Pentazocine • Phenazocine • Quadazocine • Thiazocine • Tonazocine • Volazocine • Zenazocine

4-Phenylpiperidines

Pethidines (Meperidines)	Allylnorpethidine • Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Hydroxymethoxypethidine • Morpheridine • Oxpheneridine (Carbamethidine) • Meperidine-N-Oxide • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine

Prodines	Allylprodine • α-meprodine • α-prodine • β-meprodine • β-prodine • Isopromedol • Meprodine • MPPP • PEPAP • Prodine • Prosidol • Trimeperidine (Promedol)

Ketobemidones	Acetoxyketobemidone • Droxypropine • Ketobemidone • Methylketobemidone • Propylketobemidone

Others	Alvimopan • Loperamide • Picenadol

Open Chain
Opioids

Amidones	Dextromethadone • Dextroisomethadone • Dipipanone • Hexalgon (Norpipanone) • Isomethadone • Levoisomethadone • Levomethadone • Methadone • Methadone intermediate • Normethadone • Norpipanone • Phenadoxone (Heptazone) • Pipidone

Methadols	Acetylmethadol • α-methadol • α-acetylmethadol • β-methadol • β-acetylmethadol • Dimepheptanol (Racemethadol) • Levo-α-acetylmethadol • Noracymethadol

Moramides	Dextromoramide • Levomoramide • Moramide intermediate • Racemoramide

Thiambutenes	Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene • Piperidylthiambutene • Pyrrolidinylthiambutene • Thiambutene • Tipepidine

Phenalkoxams	Dextropropoxyphene • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Propoxyphene

Ampromides	Diampromide • Phenampromide • Propiram

Others	IC-26 • Isoaminile • Lefetamine • R-4066

Anilidopiperidines

3-Allylfentanyl • 3-Methylfentanyl • 3-Methylthiofentanyl • Alfentanil • α-methylacetylfentanyl • α-methylfentanyl • α-methylthiofentanyl • Benzylfentanyl • β-hydroxyfentanyl • β-hydroxythiofentanyl • β-methylfentanyl • Brifentanil • Carfentanil • Fentanyl • Lofentanil • Mirfentanil • Ocfentanil • Ohmefentanyl • Parafluorofentanyl • Phenaridine • Remifentanil • Sufentanil • Thenylfentanyl • Thiofentanyl • Trefentanil

Oripavine
derivatives

7-PET • Acetorphine • Alletorphine • BU-48 • Buprenorphine • Butorphine • Cyprenorphine • Dihydroetorphine • Diprenorphine (M5050) • Etorphine • N-cyclopropylmethyl-noretorphine • Nepenthone • Norbuprenorphine • Thevinone • Thienorphine

Phenazepines

Ethoheptazine • Meptazinol • Metheptazine • Metethoheptazine • Proheptazine

Pirinitramides

Bezitramide • Piritramide

Benzimidazoles

Clonitazene • Etonitazene • Nitazine

Indoles

7-Acetoxymitragynine • 7-Hydroxymitragynine • Akuammidine • Akuammine • Eseroline • Hodgkinsine • Ibogaine • Mitragynine • Pericine • ψ-Akuammigine

Diphenylmethylpiperazines

BW373U86 • DPI-221 • DPI-287 • DPI-3290 • SNC-80

Opioid Peptides

Casomorphin • DADLE • DALDA • DAMGO • Dermenkephalin • Dermorphin • Deltorphin • DPDPE • Dynorphin • Endomorphin • Endorphin • Enkephalin • Gliadorphin • Morphiceptin • Nociceptin • Octreotide • Opiorphin • Rubiscolin • TRIMU 5

Others

4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol • Azaprocin • Bisnortilidine • C-8813 • Ciramadol • Cyclohexyloxy-α-phenethylamine • Enadoline • Faxeladol • Herkinorin • JTC-801 • Methopholine • NNC 63-0532 • Nortilidine • O-Desmethyltramadol • Prodilidine • Salvinorin A • SC-17599 • RWJ-394,674 • TAN-67 • Tapentadol • Tifluadom • Tilidine • Tramadol • Viminol • W-18 • Zipeprol

Opioid Antagonists

5'-Guanidinonaltrindole • β-Funaltrexamine • 6β-Naltrexol • Alvimopan • Amiphenazole • Binaltorphimine • Clocinnamox • Cyclazocine • Cyprodime • Diprenorphine (M5050) • Fedotozine • Levallorphan • Methocinnamox • Methylnaltrexone • Nalfurafine • Nalmefene • Nalmexone • Naloxazone • Naloxonazine • Naloxone • Naloxone benzoylhydrazone • Nalorphine • Naltrexone • Naltriben • Naltrindole • Norbinaltorphimine • Oxilorphan • S-allyl-3-hydroxy-17-thioniamorphinan (SAHTM)

Wikipedia content modification information:

This page was last modified on 4 September 2008, at 19:13.

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