Dipipanone
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|---|---|
| Systematic (IUPAC) name | |
| 4,4-Diphenyl-6-(1-piperidinyl)-heptan-3-one | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Schedule I (USA) CD Schedule 2 Class A (UK) |
| Routes | Oral, Intravenous |
| Identifiers | |
| CAS number | 467-83-4  |
| ATC code | None |
| PubChem | CID 13331 |
| DrugBank | DB01491 |
| ChemSpider | 12766  |
| UNII | verifiedrevid = 460793100 X188638Y2V verifiedrevid = 460793100 |
| Chemical data | |
| Formula | C24H31NO |
| Mol. mass | 349.52 |
| SMILES | eMolecules & PubChem |
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Dipipanone[1] is a strong opioid analgesic drug, used for very severe pain in cases where other analgesics are unsuitable, for instance where morphine is indicated but cannot be used due to the patient being allergic to morphine.
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[edit] Dosage forms
The main preparation of the drug commercially available is mixed with cyclizine (Diconal, Wellconal) which has the advantage of reducing nausea, vomiting and histamine release associated with strong opioid therapy.[2]
Dipipanone was also available as a oral mixture 10mg/5ml without the cyclizine during the 1970's - 1980's in the UK. This form was rare and used normally only in drug trials and in specialist diconal addiction clinics like the one in cheltenham spa back then.
[edit] Usage
Dipipanone is now unavailable in most countries of the world either by laws prohibiting its medicinal use as in the United States or by falling out of production as more modern analgesics took its market share. The UK, Northern Ireland and South Africa are known to continue to use the substance but it is infrequently prescribed.
[edit] Chemistry
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. Other related compounds with equivalent activity where the piperidine ring has been replaced by other groups, include the morpholine derivative phenadoxone, as well as the corresponding pyrrolidine derivative.[3] The general procedure for synthesis is illustrated by nucleophilic attack of diphenylacetonitrile on 2-chloro-1-piperidyl-propane. 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.[4][5]
[edit] Medical use and recreational abuse
Prescription of dipipanone is discouraged apart from in exceptional circumstances, because of the perceived risk of abuse - the BNF marks the substance as "less suitable for prescribing" along with other older compounds such as pethidine and pentazocine with unusual abuse patterns. The combination with cyclizine leads to a very strong "rush" if the drug is injected, however the tablets contain insoluble binders which led to many limb amputations and some fatalities (as with temazepam). 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 or Physeptone ampoules with crushed Valoid (a cyclizine containing antihistamine) tablets, in an attempt to replicate the effect of Diconal.
[edit] References
- ^ GB patent 654975, Peter Ofner, Eric Walton, "Improvements relating to the Synthesis of Diphenyl Ketones", published 1948-02-09, issued 1951-07-04
- ^ Fang, Glover, Jarman, Gorrod: Inhibition of monoamine oxidase B by dipipanone and cyclizine. Pharmaceutical Sciences (1995), 1(6), 295-296.
- ^ Lenz GR, Evans SM, Walters DE, Hopfinger AJ. Opiates (1986). pp406-407. Academic Press. ISBN 978-0124438309
- ^ P. A. J. Janssen, Synthetic Analgesics. Part 1. Diphenylpropylamines, 1960, Pergamon Press, NY
- ^ Casy AF, Pargitt RY. Opioid analgesics, chemistry and receptors. 1986, Plenum Press, New York. ISBN 0306421305
