Desoxypipradrol
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Desoxypipradrol
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| Systematic (IUPAC) name | |
| 2-benzhydrylpiperidine | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C18H21N |
| Mol. mass | 251.366 g/mol |
| Pharmacokinetic data | |
| Bioavailability | >90% |
| Metabolism | Hepatic |
| Half life | 16-20 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | Oral |
Desoxypipradrol, (also referred to as Deoxypipradrol, 2-(diphenylmethyl)piperidine or 2-DPMP), is a long-acting stimulant drug that is chemically and mechanistically related to methylphenidate and pipradrol. All three compounds function as catecholamine reuptake inhibitors, exerting inhibitory effects on the neuronal dopamine (DAT) and noradrenaline (NET) transporter proteins.[1] Of these three piperidine stimulants, 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 metabolised groups.
Desoxypipradrol was developed by the pharmaceutical company Ciba-Geigy (now called Novartis) in the 1950s, 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 to facilitate rapid recovery from anaesthesia [2] 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. Despite these potential side effects, a few anecdotal reports of recreational use have surfaced on bulletin boards focusing on drug use.
Desoxypipradrol might also prove quite useful for its original application of treating attention-deficit hyperactivity disorder, considering that the short half-life of common treatments such as methylphenidate and dextroamphetamine has led to the development of long-acting, delayed release formulations of these drugs. Certain individuals with ADHD prefer long-acting stimulant compounds, as they often require only one daily dose, making it more difficult to forget to take the medication. However, if desoxypipradrol attracts significant media attention as a drug of abuse, it may quickly become illegal and fade back into obscurity.[citation needed]
Desoxypipradrol is not specifically listed as an illegal drug in any country at the present time, but its structural similarity to the illegal drug pipradrol makes it possible that it would be considered a controlled substance analogue in several countries such as Australia and New Zealand.
Desoxypipradrol has shown some promise in privately funded studies at reducing or eliminating instances of sleep paralysis.
[edit] References
- ^ 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.
- ^ 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.
