Desoxypipradrol
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| Clinical data | |
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| Routes of administration | oral, nasal and sublingual |
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| Pharmacokinetic data | |
| Bioavailability | >90% |
| Metabolism | Hepatic |
| Elimination half-life | 16-20 hours |
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| ECHA InfoCard | 100.007.525  |
| Chemical and physical data | |
| Formula | C18H21N |
| Molar mass | 251.366 g/mol g·mol−1 |
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Desoxypipradrol, also known as 2-diphenylmethylpiperidine (2-DPMP) 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.
Desoxypipradrol might 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. As of the 4th November 2010, the UK Home Office announced a ban on the importation of 2-DPMP, following a recommendation from the ACMD. [4].
See also
References
- ^ 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.
- ^ Tripod J, Sury E, Hoffmann K. Zentralerregende Wirkung eines neuen Piperidinderivates. (German) Experientia 1954; 10:261-262.
- ^ 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.
- ^ http://www.homeoffice.gov.uk/media-centre/news/drug-import-ban
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