Dipipanone

From Wikipedia, the free encyclopedia


Dipipanone
Systematic (IUPAC) name
4,4-Diphenyl-6-(1-piperidinyl)-3-heptanone
Identifiers
CAS number	467-83-4
ATC code	?
PubChem	?
Chemical data
Formula	C₂₄H₃₁N O
Mol. mass	349.52
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Dipipanone hydrochloride is an opioid painkiller. In combination with cyclizine hydrochloride, it is marketed as Diconal, indicated for relief of moderate to severe pain.

Chemically, dipipanone belongs to the class of opiates called the 3-diphenyl heptanones. It closely resembles methadone, the only structural difference being the N,N-dimethyl moiety of methadone being replaced with a piperidine ring. Its usage is now officially discouraged because of the abuse risk. The combination with cyclizine lends a very strong rush if the drug is injected. During the late 1970s to early 1980s in the UK, a whole spate of deaths were blamed on this preparation. As supplies became unavailable, opiate users would mix crushed methadone tablets with crushed Valoid (a cyclizine containing antihistamine) tablets in an attempt to replecate the affect of dipipanone.

See P. A. J. Janssen, Synthetic Analgesics. Part 1. Diphenylpropylamines, Pergamon Press, NY. for details on the synthesis of methadone and its cogeners before 1960. The general procedure for synthesis is illustrated by nucleophillic attack of diphenylacetonitrile on 2-chloro--1-dimethylaminoethane. The resulting aminonitrile is then converted to the ethyl ketone with ethyl magnesium bromide by way of the kitimine which is hydrolized by cold aqueous acid (Casey & Parfitt, Opioid Analgesics, Plenum Press, NY, london).

[edit] External links

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

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 • 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 • Nalbuphine • 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 (Norpipanone) • 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 • Pyrrolidinylthiambutene • Tipepidine

Phenalkoxams	Dextropropoxyphene • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Propoxyphene

Ampromides	Diampromide • Phenampromide • Propiram

Others	IC-26 • Lefetamine • R-4066