Desoxypipradrol

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

Desoxypipradrol, also known as 2-diphenylmethylpiperidine (2-DPMP), acts as a norepinephrine-dopamine reuptake inhibitor (NDRI)[1] developed by Ciba in the 1950s[2]

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,[3] 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[4]), 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.[5]

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 and this would have been fatal[citation needed] 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 [6] that:

"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)."

See also

References

  1. ^ a b Ferris, RM; Tang, FL (1979). "Comparison of the effects of the isomers of amphetamine, methylphenidate and deoxypipradrol on the uptake of l-3Hnorepinephrine and 3Hdopamine by synaptic vesicles from rat whole brain, striatum and hypothalamus". The Journal of pharmacology and experimental therapeutics 210 (3): 422–8. PMID 39160. 
  2. ^ US Patent 2820038 - 2-Diphenyl-Methyl-Piperidine
  3. ^ Tripod J, Sury E, Hoffmann K. (1954). "Zentralerregende Wirkung eines neuen Piperidinderivates. (German)". Experientia 10 (6): 261–262. doi:10.1007/BF02157398. PMID 13183068. 
  4. ^ Bellucci, G (1955). "(2-Diphenylmethyl-piperidine hydrochloride and the methyl ester of 2-chloro-2-phenyl-2-(2-piperidyl)-acetic acid), drugs with waking effect in anesthesia.". Minerva anestesiologica 21 (6): 125–8. PMID 13244387. 
  5. ^ Import ban on psychoactive drug, UK Home Office
  6. ^ [1], ACMD Report on Ivory Wave

Wikimedia Foundation. 2010.

Игры ⚽ Нужен реферат?

Look at other dictionaries:

  • Desoxypipradrol — Strukturformel (R) Form (links) und (S) Form (rechts) …   Deutsch Wikipedia

  • desoxypipradrol — noun 2 diphenylmethylpiperidine, a psychoactive drug and research chemical of the piperidine class …   Wiktionary

  • Diphenylprolinol — Systematic (IUPAC) name diphenyl(pyrrolidin 2 yl)methanol Clinical data Pregnancy cat.  ? …   Wikipedia

  • Aminorex — Systematic (IUPAC) name (RS) 5 phenyl 4,5 dihydro 1,3 oxazol 2 amine Clinical data Pregnancy cat.  …   Wikipedia

  • Diphenylpyraline — Systematic (IUPAC) name 4 benzhydryloxy 1 methyl piperidine Clinical data AHFS/Drugs.com …   Wikipedia

  • Pipradrol — Systematic (IUPAC) name α,α Diphenyl 2 piperidinemethanol Clinical data Pregnancy cat.  ? …   Wikipedia

  • RTI-31 — Systematic (IUPAC) name methyl (1R,2S,3S,5S) 3 (4 chlorophenyl) 8 methyl 8 azabicyclo[3.2.1]octane 2 carboxylate Clinical data Pregnancy cat …   Wikipedia

  • Difemetorex — Systematic (IUPAC) name 2 [2 (diphenylmethyl)piperidin 1 yl]ethanol Clinical data Pregnancy cat.  ? …   Wikipedia

  • Amphetamine — For other uses, see Amphetamine (disambiguation). Amphetamine Systematic (IUPAC) name …   Wikipedia

  • Modafinil — Systematic (IUPAC) name (±) 2 (benzhydrylsulfinyl)acetamide …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”