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20-September-2008 09:55:55 - Desoxypipradrol Desoxypipradrol Systematic IUPAC name 2-benzhydrylpiperidine Identifiers CAS number 519-74-4 ATC code ? PubChem 160506 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-diphenylmethylpiperidine 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.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. References ^ Ferris RM Tang FL. 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. J Pharmacol Exp Ther. 1979. 2103:422-8. ^ 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;216:125-8. v d e Stimulants Alkylamines Cyclopentamine Geranamine Isometheptene Octodrine Propylhexedrine Tuamine Alphapyrrolidinylalkiophenones α-PPP MDPPP MDPV MPBP MPHP MPPP MOPPP Pyrovalerone Cholinergics ABT-089 ABT-418 Anabasine Arecoline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine Rivanicline Tebanicline Varenicline Convulsants Bicuculline DMCM Gabazine Pentetrazol Picrotoxin Strychnine Thujone Eugeroics Adrafinil Armodafinil Carphedon Modafinil Phenethylamines 4-Bromomethcathinone 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-Fluoromethcathinone 4-Methylmethcathinone 4-MTA Aletamine Amfepentorex Amphechloral Amphetamine Dextroamphetamine, Adderall Amphetaminil Benzphetamine Bupropion Cathinone Chlorphentermine Clenbuterol Clobenzorex Clortermine Diethylpropion Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Ephedrine Epinephrine Ethcathinone Ethylamphetamine Fenethylline Fenfluramine Fenproporex Fludorex Furfenorex Levomethamphetamine Lisdexamfetamine MDMA Mefenorex Methamphetamine Methcathinone Methoxyphedrine Methylone Octopamine Ortetamine Parahydroxyamphetamine PCA PIA PMA PMEA PMMA PPAP Phendimetrazine Phenmetrazine Phentermine Phenylephrine Phenylpropanolamine Propylamphetamine Pseudoephedrine Selegiline Synephrine Tiflorex Xylopropamine Phenylaminooxazoles 4-Methyl-aminorex Aminorex Clominorex Fenozolone Fluminorex Pemoline Thozalinone Piperazines 2C-B-BZP BZP GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP Vanoxerine Piperidines 2-Benzylpiperidine Desoxypipradrol Diphemethoxidine Ethylphenidate HDMP-28 --Methyl-1-methyl-4β-2-naphthylpiperidine-3β-carboxylate Methylphenidate Dexmethylphenidate Nocaine Phacetoperane Pipradrol Tropanes 3α-Bis-4-fluorophenylmethoxytropane 3α-4-Chlorophenylphenylmethoxytropane 3-Pseudotropyl-4-fluorobenzoate Altropane IACFT Brasofensine CFT WIN 35,428 β-CIT RTI-55 Cocaethylene Cocaine β-CPPIT Dichloropane RTI-111 Difluoropine FE-β-CPPIT FP-β-CPPIT PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-121 IPCIT RTI-126 RTI-150 RTI-171 RTI-177 RTI-336 Tesofensine Troparil β-CPT, WIN 35,065-2 WF-23 WF-33 WF-60 Xanthines Aminophylline Caffeine Dimethazan Paraxanthine Theobromine Theophylline Others Amineptine Bemegride Benzydamine BPAP Bromantane BTQ Clofenciclan Cypenamine Cyprodenate Diclofensine Dimethocaine Diphenyl prolinol Ethamivan Fencamfamine Feprosidnine Gilutensin GYKI-52895 Hexacyclonate Indanorex Indatraline LR-5182 Mazindol Mesocarb Naphthylisopropylamine Nikethamide Nomifensine Phthalimidopropiophenone Prolintane Sibutramine Yohimbine Zylofuramine See also Sympathomimetic amines Retrieved from http://en..org/wiki/Desoxypipradrol Categories: Stimulants | PiperidinesHidden categories: All articles with statements | Articles with statements since February 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch This page was last modified on 4 August 2008, at 06:55
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