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20-September-2008 09:55:55 - Adrafinil Adrafinil Systematic IUPAC name 2-benzhydrylsulfinylethanehydroxamic acid Identifiers CAS number 63547-13-7 ATC code N06BX17 PubChem 3033226 Chemical data Formula C15H15NO3S Mol. mass 289.351 g/mol SMILES eMolecules PubChem Pharmacokinetic data Bioavailability ? Metabolism ? Half life ? Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Routes Oral Adrafinil is a mild central nervous system stimulant drug used to relieve excessive sleepiness and inattention in elderly patients. It is also used off-label by individuals wishing to avoid fatigue, such as night workers or others who need to stay awake and alert for long periods of time. Adrafinil is a prodrug; it is primarily metabolized in vivo to modafinil Provigil, resulting in nearly identical pharmacological effects. Unlike modafinil, however, it takes time for the metabolite to accumulate to active levels in the bloodstream. Effects usually are apparent within 45-60 minutes when taken orally on an empty stomach. Adrafinil, also known by the codename CRL 40028, has as its chemical name 2-Diphenylmethyl sulfinyl acetohydroxamic acid. Its molecular formula is C15H15NO3S. The drug's molecular weight is 289.4 Daltons. Adrafinil does not currently have FDA approval and is thus unregulated in the United States, although it is used in France and elsewhere in Europe. The drug is marketed under the brand name Olmifon by the American pharmaceutical company Cephalon, which acquired Group Lafon in 2001. Contents 1 History 2 Legal status 2.1 Usage detection 3 References 4 See also 5 External links History Adrafinil was discovered in the late 1970s by scientists working with the French pharmaceutical company Group Lafon. The drug was first offered as an experimental treatment for narcolepsy in France in 1986. Later on, Lafon scientists developed modafinil as a stand-alone drug because the latter drug was understood to be a more highly selective alpha-1 adrenergic and also featured less in the way of side effects such as stomach pain, skin irritations, feelings of tension, and an increase in liver enzyme levels. Legal status Adrafinil and its close relative modafinil were added to the list of substances prohibited for athletic competition according to World Anti-Doping Agency in 2004.1 In the United States, adrafinil is currently unregulated. It has not been approved for any clinical uses by the U.S. Food and Drug Administration. Unlike modafinil, adrafinil is not classified as a controlled substance and does not fall under DEA jurisdiction; in particular, it is not illegal to possess without a prescription and can be imported privately by citizens.citation needed Usage detection The metabolites of Adrafinil as well as Modafinil contain sulfur, and can easily be detected by a peculiar odour of the urine of the person who has taken it.citation needed References ^ World Anti-Doping Agency - 2007 prohibited list SID 184744 -- PubChem Substance Summary. The PubChem Project. National Center for Biotechnology Information. Retrieved on 7 December, 2005. See also Modafinil Ampakines External links Adrafinil: A Novel Vigilance Promoting Agent by Norton W. Milgram, Heather Callahan, and Christina Siwak of the University of Toronto at Scarborough, CNS Drug Reviews, Vol. 5, No. 3, pp. 193-212 PDF Adrafinil-induced orofacial dyskinesia. by Thobois S, Xie J, Mollion H, Benatru I, Broussolle E. of the Department of Neurology, The Pierre Wertheimer Neurological Hospital, Lyon, France 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 v d e Psychoanaleptics: psychostimulants, agents used for ADHD and nootropics N06B Centrally acting sympathomimetics Amphetamine - Amphetaminil - Atomoxetine - Dextroamphetamine - Dextromethamphetamine - Fencamfamin - Fenozolone - Fenetylline - Methylphenidate - Mesocarb - Pemoline - Pipradrol - Prolintane Xanthine derivatives Caffeine - Propentofylline Glutamate receptor Racetams Aniracetam - Nefiracetam - Oxiracetam - Phenylpiracetam - Piracetam - Pramiracetam Ampakines CX-516 - CX-546 - CX-614 - CX-691 - CX-717 - IDRA-21 - LY-503,430 - PEPA Eugeroics / Benzhydryl compounds Adrafinil - Armodafinil - Modafinil Histamine H3 receptor antagonists ABT-239 - Ciproxifan Other psychostimulants and nootropics Acetylcarnitine - Citicoline - Cyprodenate - Idebenone - Ispronicline - Deanol - Dimebon - Fipexide - Linopirdine - Meclofenoxate - Nizofenone - Pirisudanol - Pyritinol - Sulbutiamine - Taltirelin - Tricyanoaminopropene - Vinpocetine Retrieved from http://en..org/wiki/Adrafinil Categories: Stimulants | Nootropics | Prodrugs | Sulfoxides | Hydroxamic acidsHidden categories: All articles with statements | Articles with statements since May 2008 | Articles with statements since February 2007 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 Français Galego Nederlands This page was last modified on 30 May 2008, at 20:0
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