Azidomorphine

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Azidomorphine
Systematic (IUPAC) name
6-β-azido-4,5-α-epoxy-17-methyl-morphinan-3-ol
Identifiers
CAS number	22952-87-0
ATC code	?
PubChem	5488848
Chemical data
Formula	C₁₇H₂₀N₄O₂
Mol. mass	312.366 g/mol
SMILES	eMolecules & PubChem
Synonyms	Azidomorphine
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Azidomorphine is an opiate analogue that is a derivative of morphine, where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an azide group.^[1]

Azidomorphine binds with high affinity to the mu opioid receptor,^[2] and is around 40x more potent than morphine in vivo. It has similar effects to other opioid agonists including analgesia, sedation and respiratory depression. However its addiction liability has been found to be slightly lower than that of morphine in animal studies.^[3]^[4]

References

^ Knoll J, Furst S, Kelemen K. The pharmacology of azidomorphine and azidocodeine. Journal of Pharmacy and Pharmacology. 1973;25(12):929-939. PMID 4150295
^ Horváth K, Wollemann M. Azidomorphine is an agonist of high-affinity opioid receptor binding sites. Neurochemical Research. 1986 Nov;11(11):1565-9. PMID 2825053
^ Knoll J. Azidomorphines: a new family of potent analgesics with low dependence capacity. Progress in Neuropsychopharmacology. 1979;3(1-3):95-108. PMID 45567
^ Hill RC, Roemer D, Buescher H. Investigations of the analgesic and morphine-like properties of azidomorphine. Journal of Pharmacology and Experimental Therapeutics. 1977 Jun;201(3):580-6. PMID 405472

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	Bulbocapnine • Codeine • Cotarnine • Eupaverine • Glaucine • Hydrocotarnine • Laudanosine • Laudanine • Morphine • Narceine • Narcotine • Narcotoline • Neopine • Noscapine • Papaverine • Papaveraldine • Perparin • Porphyroxine • Pseudomorphine • Oripavine • 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

Codeine-Dionine Family	6-acetylcodeine • Acetylcodeine • Azidomorphine • Benzylmorphine • Codeine • Desocodeine • Dihydroheterocodeine • Ethylmorphine (Dionine) • Heterocodeine • Isocodeine • Morpholinylethylmorphine • Myrophine • Nalodeine

Morphinones	14-Ethoxymetopon • 14-Methoxymetopon • 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 • 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 • Dihydroisocodeine • Nicocodeine • Nicodicodeine

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

Other µ-opioid Agonists	Chloromorphide • α-chlorocodide • Pholcodine

Antagonists	Clocinnamox • Methylnaltrexone • Nalfurafine • Nalmefene • Nalorphine • Naloxone • Naltrexone • Naltrindole

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	Cyclorphan • Dextro-3-hydroxy-N-allylmorphinan • Dextromethorphan • Dextrorphan • Dimemorfan • Levargorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Racemethorphan • Racemorphan • Xorphanol

Others	6-Ketonalbuphine • Aknadinine • Butorphanol • Cyprodime • Drotebanol • Nalbuphine • Salutaridine (Sinoacutine) • Sinococuline • Sinomenine (Cocculine)

Benzomorphans

5,9-DEHB • 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	Diallylthiambutene • Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene • Methylisopropylthiambutene • Methylpropylthiambutene • Morpholinylthiambutene • 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 • Cyprenorphine • Dihydroetorphine • Diprenorphine • 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 • 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 • 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 • Salvinorin A • SC-17599 • RWJ-394,674 • Tapentadol • Tifluadom • Tilidine • Tramadol • Viminol • W-18 • Zipeprol

Narcotic Antagonists

5'-Guanidinonaltrindole • β-Funaltrexamine • Amiphenazole • Binaltorphimine • Cyclazocine • Cyclohexyloxy-α-phenethylallylamine • Diprenorphine • Fedotozine • M5050 • Levallorphan • Methylnaltrexone • Nalmefene • Naloxazone • Naloxonazine • Naloxone • Naloxone benzoylhydrazone • Nalorphine • Naltrexone • Naltrindole • Norbinaltorphimine • Oxilorphan

Active Precursors,
Intermediates & Byproducts

3-Monoacetylmorphine • 6-acetylcodeine • 6-Monoacetylmorphine • Acetylcodeine • Dihydromorphine • Dipehnoxylic Acid • Dromoran (racaemic) • Monacetylmorphine • Morphine • Moramide intermediate • MPP+ • MPPP • MPTP • Oripavine • Parafluorofentanyl • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Poppy Straw Concentrate • Racemoramide (Moramide) • Thebaine

Wikipedia content modification information:

This page was last modified on 9 April 2008, at 10:17.

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