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| Clinical data | |
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| Routes of administration | By mouth, nasal and sublingual |
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| Pharmacokinetic data | |
| Bioavailability | >90% |
| Metabolism | Liver |
| Eliminationhalf-life | 16–20 hours |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.007.525 |
| Chemical and physical data | |
| Formula | C18H21N |
| Molar mass | 251.373 g·mol−1 |
| 3D model (JSmol) | |
| Chirality | Racemic mixture |
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Desoxypipradrol, also known as2-diphenylmethylpiperidine (2-DPMP), is a drug developed by Ciba in the 1950s[1] which acts as anorepinephrine-dopamine reuptake inhibitor (NDRI).[2]
Desoxypipradrol is closely related on astructural level to the compoundsmethylphenidate andpipradrol, all three of which share a similarpharmacologicalaction.[2] Of these threepiperidines, desoxypipradrol has the longest eliminationhalf-life, as it is a highlylipophilicmolecule lackingpolarfunctional groups that are typically targeted bymetabolicenzymes, giving it an extremely long duration of action when compared to most psychostimulants. Methylphenidate, on the other hand, is a short-acting compound, as it possesses amethyl-estermoiety that is easily cleaved, forming a highly polaracid group, while pipradrol (desoxypipradrol's intermediate) has shorter duration due to ahydroxyl group which can beconjugated (e.g. withglucuronide) to increase itshydrophilicity and facilitateexcretion, but pipradrol itself has no easily metabolizable groups.
Desoxypipradrol was developed by the pharmaceutical company CIBA (now calledNovartis) in the 1950s,[3] and researched for applications such as the treatment ofnarcolepsy andADHD; 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 predictablepharmacokinetics, and while desoxypipradrol was researched for other applications (such as facilitation of rapid recovery fromanaesthesia[4]), its development was not continued. The hydroxylated derivativepipradrol was, however, introduced as a clinical drug indicated fordepression,narcolepsy and cognitive enhancement in organicdementia.
Desoxypipradrol may be quantitated inblood,plasma orurine by liquid chromatography-mass spectrometry to confirm a diagnosis of poisoning in hospitalized patients or to provide evidence in a medicolegal death investigation. Blood or plasma desoxypipradrol concentrations are expected to be in a range of 10–50 μg/L in persons using the drug recreationally, >100 μg/L in intoxicated patients and >600 μg/L in victims of acute overdosage.[5]
Desoxypipradrol's structural similarity topipradrol makes it possible that it would be considered acontrolled substance analogue in several countries such asAustralia andNew Zealand.
As of October 2015 2-DPMP is a controlled substance in China.[6]
As of 4 November 2010, theUKHome Office announced a ban on the importation of 2-DPMP, following a recommendation from theACMD.[7]
Prior to the import ban, desoxypipradrol was sold as a 'legal high' in several products, most notably "Ivory wave". Its use lead to severalEmergency Department visits which prompted theUK government to commission a review from theACMD. One man had ingested nearly 1 gram of the drug which may have been fatal without sedation with an anaesthetic dose of a benzodiazepine administered in accident and emergency.[citation needed]
The Advisory Council on the Misuse of Drugs stated in their report[8] that:
2-DPMP was due to become a class B drug[9] on 28 March 2012,[10] but the bill was scrapped as two steroids deemed not to be abusable were included in the bill but were later recommended to remain uncontrolled.[11] There was a new discussion about its fate on April 23, 2012, where it was decided that the bill would be rewritten and 2-DPMP would still be banned. It was also decided that the bill would be a blanket ban of related chemicals.[12]
Desoxypipradrol was eventually made a class B drug and placed in Schedule I on 13 June 2012.[13] There were no recorded deaths from the drug between the banning of its import and the banning of its possession. "Esters and ethers of pipradrol" were controlled with the same amendment as class C drugs.[13]
