Dipropanoylmorphine

You don't need to be Editor-In-Chief to add or edit content to WikiDoc. You can begin to add to or edit text on this WikiDoc page by clicking on the edit button at the top of this page. Next enter or edit the information that you would like to appear here. Once you are done editing, scroll down and click the Save page button at the bottom of the page.

Image:Dipropanoylmorphine.png
Dipropanoylmorphine
Systematic (IUPAC) name
(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-dipropionate
Identifiers
CAS number	10589-79-4
ATC code	?
PubChem	165894
Chemical data
Formula	C23H27NO5
Mol. mass	397.464 g/mol
Synonyms	Dipropanoylmorphine
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Schedule I(US)
Routes	?

Dipropanoylmorphine is an opiate derivative, the 3,6-dipropanoyl ester of morphine. It was developed in the 1970s as an analgesic. ^[1] It is rarely used in some countries for the relief of severe pain such as that caused by terminal cancer, as an alternative to diamorphine (heroin) and morphine.

Dipropanoylmorphine is slightly slower acting than diamorphine, but longer lasting, and is slightly more potent due to its relatively higher lipophilicity. ^[1] Side effects are similar to those of other opioids and include itching, nausea and respiratory depression.

Dipropanoylmorphine is prepared by reacting morphine with propanoic anhydride, in an analogous manner to how heroin is produced by reacting morphine with acetic anhydride.

While acetic anhydride is a restricted chemical around the world due to its potential uses in making heroin, it is used in vast amounts by the chemical industry for the manufacture of drugs such as aspirin. Propanoic anhydride however is much less widely used. Although it is used in the manufacture of a range of pharmaceuticals, none of these are produced in nearly as large quantities, and sales of propanoic anhydride in quantities larger than one gram must be reported in many countries because of its potential use in making fentanyl type synthetic opiates.

References

v • d • e 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
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
Phenazepines	Ethoheptazine • Meptazinol • Metheptazine • Metethoheptazine • Proheptazine
Pirinitramides	Bezitramide • Piritramide
Benzimidazoles	Clonitazene • Etonitazene
Indoles	7-Acetoxymitragynine • 7-Hydroxymitragynine • Akuammidine • Akuammine • Eseroline • 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 • TRIMU 5
Others	4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol • C-8813 • Ciramadol • Enadoline • Faxeladol • Herkinorin • JTC-801 • Methopholine • NNC 63-0532 • Noscapine/Narcotine • O-Desmethyltramadol • Salvinorin A • RWJ-394,674 • Tapentadol • Tifluadom • Tilidine • Tramadol • Viminol • W-18 • Zipeprol
Narcotic Antagonists	5'-Guanidinonaltrindole • β-Funaltrexamine • Binaltorphimine • Cyclazocine • Cyclohexyl-alpha-phenethylallylamine • Diprenorphine • M5050 • Levallorphan • Nalmefene • Naloxazone • Naloxonazine • Naloxone • Nalorphine • Naltrexone • Naltrindole • Norbinaltorphimine • Oxilorphan