14-Methoxymetopon

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14-Methoxymetopon
Systematic (IUPAC) name
3-hydroxy-14-methoxy-5,17-dimethyl-7,8-dihydro-4,5α-epoxy-morphinan-6-one
Identifiers
CAS number	131575-03-6
ATC code	?
PubChem	5486940
Chemical data
Formula	C₁₉H₂₃N O₄
Mol. mass	329.39 g/mol
SMILES	eMolecules & PubChem
Synonyms	14-Methoxymetopon
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

14-Methoxymetopon is an opiate analogue that is an derivative of metopon which has been substituted with a methoxy group at the 14-position. It is a highly potent analgesic drug that is around 500x stronger than morphine when administered systemically; however, when given spinally, it is up to 1 million times the potency of morphine.^[1] It binds strongly to the μ-opioid receptor and activates it to a greater extent than most similar opioid drugs.^[2] This produces an unusual pharmacological profile, and although 14-methoxymetopon acts as a potent μ-opioid full agonist in regards to some effects such as analgesia, a ceiling effect is seen on other effects such as constipation and respiratory depression.^[3]

References

^ King MA, Su W, Nielan CL, Chang AH, Schütz J, Schmidhammer H, Pasternak GW. 14-Methoxymetopon, a very potent mu-opioid receptor-selective analgesic with an unusual pharmacological profile. European Journal of Pharmacology. 2003 Jan 17;459(2-3):203-9. PMID 12524147
^ Mahurter L, Garceau C, Marino J, Schmidhammer H, Tóth G, Pasternak GW. Separation of binding affinity and intrinsic activity of the potent mu-opioid 14-methoxymetopon. Journal of Pharmacology and Experimental Therapeutics. 2006 Oct;319(1):247-53. PMID 16801454
^ Freye E, Schmidhammer H, Latasch L. 14-methoxymetopon, a potent opioid, induces no respiratory depression, less sedation, and less bradycardia than sufentanil in the dog. Anesthesia and Analgesia. 2000 Jun;90(6):1359-64. PMID 10825321

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v • d • e

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

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 • 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 • 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 • Naltrindole • Norbinaltorphimine • Oxilorphan • S-allyl-3-hydroxy-17-thioniamorphinan (SAHTM)

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This page was last modified on 23 April 2008, at 06:34.

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