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Dipipanone
Systematic (IUPAC) name
4,4-Diphenyl-6-(1-piperidinyl)-heptan-3-one
Identifiers
CAS number 467-83-4
ATC code none
PubChem 13331
Chemical data
Formula C 24H31NO 
Mol. mass 349.52
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes Oral, Intravenous

Dipipanone is an opioid analgesic. Its hydrochloride form, in combination with cyclizine hydrochloride, is marketed as Diconal, indicated for relief of moderate to severe pain.

Chemically, dipipanone belongs to the class of opioids called the 4,4-diphenylheptane-3-ones. It closely resembles methadone, the only structural difference being the N,N-dimethyl moiety of methadone being replaced with a piperidine ring. Its use is discouraged because of the abuse risk. The combination with cyclizine leads to a very strong rush if the drug is injected. During the late 1970s to early 1980s in the UK, many deaths were blamed on misuse of 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 replicate the effect of dipipanone.

The general procedure for synthesis is illustrated by nucleophilic attack of diphenylacetonitrile on 2-chloro-1-dimethylamino-ethane. The resulting aminonitrile is then converted to the ethyl ketone with ethyl magnesium bromide by way of the ketimine which is hydrolyzed by cold aqueous acid.[1][2]

References

  1. ^ P. A. J. Janssen, Synthetic Analgesics. Part 1. Diphenylpropylamines, Pergamon Press, NY
  2. ^ Casey & Parfitt, Opioid Analgesics, Plenum Press, NY, London
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