Desoxypipradrol, also known as 2-diphenylmethylpiperidine ( 2-DPMP), is a drug developed by Ciba in the 1950s[US Patent 2820038 - 2-Diphenyl-Methyl-Piperidine] which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI).
Chemistry
Desoxypipradrol is closely related on a structural level to the compounds
methylphenidate and
pipradrol, all three of which share a similar
pharmacological action.
Of these three
, desoxypipradrol has the longest elimination
half-life, as it is a highly
lipophilic molecule lacking polar
that are typically targeted by
metabolic , 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 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.
History
Desoxypipradrol was developed by the pharmaceutical company CIBA (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 facilitation of rapid recovery from
anaesthesia), 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.
Detection in biological specimens
Desoxypipradrol may be quantitated in
blood,
Blood plasma or
urine 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.
Legal status
Desoxypipradrol's 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.
China
As of October 2015 2-DPMP is a controlled substance in China.
United Kingdom
As of 4 November 2010, the UK
Home Office announced a ban on the importation of 2-DPMP, following a recommendation from the
ACMD.
[ Import ban on psychoactive drug UK Home Office]
Prior to the import ban, desoxypipradrol was sold as a 'legal high' in several products, most notably "Ivory wave". Its use lead to several Emergency Department visits which prompted the UK government to commission a review from the ACMD. 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.
The Advisory Council on the Misuse of Drugs stated in their report
- " there are serious harms associated with 2-DPMP... typically prolonged agitation (lasting up to 5 days after drug use which is sometimes severe, requiring physical restraint), paranoia, hallucinations and myoclonus (muscle spasms/twitches)."
2-DPMP was due to become a class B drug
Desoxypipradrol was eventually made a class B drug and placed in Schedule I on 13 June 2012.
See also
