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Desoxypipradrol
Systematic (IUPAC) name
2-benzhydrylpiperidine
Identifiers
CAS number 519-74-4, 5807-81-8 (HCl)
ATC code none
PubChem 160506
ChemSpider 141045
Chemical data
Formula C18H21N 
Mol. mass 251.366 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability >90%
Metabolism Hepatic
Half life 16-20 hours
Therapeutic considerations
Pregnancy cat.  ?
Legal status legal
Routes oral, nasal and sublingual

Desoxypipradrol, also known as 2-diphenylmethylpiperidine (2-DPMP), is a long-lasting psychostimulant. It acts as a norepinephrine-dopamine reuptake inhibitor (NDRI).[1]

Desoxypipradrol is closely related on a structural level to the compounds methylphenidate and pipradrol, all three of which share a similar pharmacological action.[1] Of these three piperidines, desoxypipradrol has the longest elimination half-life, as it is a highly lipophilic molecule lacking polar functional groups that are typically targeted by metabolic enzymes. Methylphenidate, on the other hand, is a short-acting compound, as it possesses a methyl-ester moiety that is easily cleaved, forming a highly polar acid group, while pipradrol is intermediate in duration, possessing a hydroxyl group which can be conjugated (e.g. with glucuronide) to increase its hydrophilicity and facilitate excretion, but no easily metabolized groups.

Desoxypipradrol was developed by the pharmaceutical company CIBA (now called Novartis) in the 1950s,[2] and researched for applications such as the treatment of narcolepsy and ADHD; however, it was dropped from development after the related drug methylphenidate was developed by the same company. Methylphenidate was felt to be the superior drug for treating ADHD due to its shorter duration of action and more predictable pharmacokinetics, and while desoxypipradrol was researched for other applications (such as facilitation of rapid recovery from anaesthesia[3]), its development was not continued. The hydroxylated derivative pipradrol was, however, introduced as a clinical drug indicated for depression, narcolepsy and cognitive enhancement in organic dementia.

In more recent times, there has been some interest in the use of desoxypipradrol as a legal recreational drug. Its activity profile as a dopamine reuptake-inhibiting stimulant means that it could potentially be used as an alternative to illegal drugs such as cocaine and methylphenidate; however, the slow onset of effects and very long duration of action (as long as 24 hours, especially if more than one dose is taken) makes it unlikely to be successful for this application, as prominent side effects such as insomnia and anorexia are likely to outweigh any positive effects.

Desoxypipradrol might also prove quite useful for its original application of treating attention-deficit hyperactivity disorder (ADHD) and depression, considering that the short half-life of common medications such as methylphenidate and dextroamphetamine has led to the development of long-acting, delayed-release formulations of these drugs. Some individuals with ADHD prefer long-acting stimulant formulations, which allow for once-daily dosing.

Desoxypipradrol is not specifically listed as a controlled drug in any country at the present time, but its structural similarity to pipradrol makes it possible that it would be considered a controlled substance analogue in several countries such as Australia and New Zealand.

See also

References

  1. ^ a b Ferris RM & Tang FL. Comparison of the effects of the isomers of amphetamine, methylphenidate and deoxypipradrol on the uptake of l-[3H]norepinephrine and [3H]dopamine by synaptic vesicles from rat whole brain, striatum and hypothalamus. J Pharmacol Exp Ther. 1979. 210(3):422-8.
  2. ^ Tripod J, Sury E, Hoffmann K. Zentralerregende Wirkung eines neven Piperidinderivates. (German) Experientia 1954; 10:261-262.
  3. ^ Bellucci G. (2-Diphenylmethyl-piperidine hydrochloride and the methyl ester of 2-chloro-2-phenyl-2-(2-piperidyl)-acetic acid), drugs with waking effect in anesthesia. (Italian). Minerva Anestesiologica. 1955 Jun;21(6):125-8.







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