M. White, J. Archer
2013
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Abstract
The syntheses of pipradrol and pipradrol derivatives and their pharmacological properties are reviewed together with details of cases of acute toxicity. Pipradrol was developed in the 1950s as an antidepressant, but the adverse effects associated with its use and its abuse potential led to its withdrawal and international control. Desoxypipradrol was first synthesised from 2-bromopyridine and diphenylacetonitrile and was originally developed as an awakening drug to reduce recovery time from anesthesia. The pyrrolidine derivatives of pipradrol, such as diphenylprolinol and 2-(diphenylmethyl)pyrrolidine, are conveniently synthesised from (S)-proline to produce the pharmacologically active stereoisomers and have been used in research as chiral catalysts. Pipradrol and pipradrol derivatives are norepinephrine and dopamine reuptake inhibitors. The relative toxicities, based on oral LD50 data in mice, are: desoxypipradrol (50)>2-(diphenylmethyl)pyrrolidine (76)>pipradrol (120)>diphenylprolinol (300). Experimentation with these drugs for recreational purposes has led to many cases of acute toxicity and desoxypipradrol has been linked to three fatalities. The social and in particular acute clinical harms of pipradrol derivatives led to their control under the Misuse of Drugs Act 1971 in the UK in 2012.