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	?

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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analogue that is a derivative of morphine, where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an azide group.^[1]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

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Opioids (N02A)

Opiate
derivatives

Whole Opium Preparations	Dover's Powder • Granulated Opium • Laudanum • Mithridate • Opium • Paregoric • Poppy Straw Concentrate • Poppy tea • Powdered Opium • Raw Opium • Smoking Opium
Natural Opiates	Codeine • Morphine • Narceine • Noscapine • Omnopon • Oripavine • Pantopon • Papaveretum • Pseudomorphine • Tetrapon • Thebaine
Semisynthetics	2,4-Dinitrophenylmorphine • 14-Hydroxyazidomorphine • 14-Ethoxymetopon • 14-Methoxymetopon • 14-Phenylpropoxymetopon • 6-Ketonalbuphine • 6-Methyldihydromorphine • 6-Methylenedihydrodesoxymorphine • 6-Methylene-14-hydroxydihydrodesoxymorphine • 8,14-Dihydroxydihydromorphinone • Acetylcodeine • Acetyldihydrocodeine • Acetylmorphone • Azidocodeine • Azidomorphine • Benzylmorphine • Chloromorphide • Clocinnamox • Codeine • Codeinone • Codorphone • Codoxime • Desocodeine • Desomorphine • Diacetyldihydromorphine • Dihydrocodeine • Dihydrocodeinone enol acetate • Dihydrohydroxycodeinone • Dihydrodesoxymorphine • Dihydroheroin • Dihydroheterocodeine • Dihydroisocodeine • Dihydromorphine • Dibutanoylmorphine • Dipropanoylmorphine • Ethyldihydromorphinone • Ethyldihydromorphine • Ethylmorphine • Heroin (Diamorphine) • Heroin-7,8-Oxide • Heterocodeine • Hydrocodone • Hydromorphinol • Hydromorphone • Isocodeine • Methyldesorphine • Methyldihydromorphine • Methylnaltrexone • Metopon • Morphinone • Myrophine • N-Phenethyl-14-ethoxymetopon • Nalbuphine • Nalfurafine • Nalmefene • Nalodeine • Nalorphine • Naloxone • Naltrexone • Naltrindole • Nicocodeine • Nicodicodeine • Nicomorphine • Oxycodone • Oxymorphone • Pholcodine • Semorphone • Thebacon
Opiate metabolites	Codeine-N-Oxide • Morphine-3-glucuronide • Morphine-6-glucuronide • Monoacetylmorphine • Morphine-N-Oxide • Naltrexol • Norcodeine • Normorphine

Morphinans

Aknadinine • Butorphanol • Cyclorphan • Cyprodime • Dextro-3-hydroxy-N-allylmorphinan • Dextromethorphan • Dextrorphan • Dimemorfan • Drotebanol • Levargorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Racemethorphan • Racemorphan • 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 • Dipipanone • Hexalgon • Isomethadone • 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	Thiambutene • Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene • Tipepidine
Phenalkoxams	Dextropropoxyphene • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Propoxyphene
Ampromides	Diampromide • Phenampromide • Propiram
Others	IC-26 • Lefetamine • R-4066