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20-September-2008 09:55:56 - Paraxanthine Paraxanthine Paraxanthine IUPAC name 1,7-Dimethylxanthine Other names paraxanthine Identifiers CAS number 611-59-6 SMILES C1C2=CNCN1C=ON=CN2C=O Properties Molecular formula C7H8N4O2 Molar mass 180.16 g/mol Melting point 351-352 °C Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Paraxanthine, or 1,7-dimethylxanthine, is a dimethyl derivative of xanthine, structurally related to caffeine. Like caffeine, paraxanthine is a psychoactive central nervous system CNS stimulant. It possesses a potency roughly equal to that of caffeine and is likely involved in the mediation of the effects of caffeine itself. Paraxanthine is not produced by plants and is only observed in nature as a metabolite of caffeine in animals. The compound is produced from caffeine 1,3,7-trimethylxanthine breakdown. After intake, roughly 84% is demethylated at the 3-position to yield paraxanthine. The drug is by far the chief metabolite of caffeine in the body. Certain proposed synthetic pathways of caffeine make use of paraxanthine as a bypass intermediate. However, its absence in plant alkaloid assays implies that these are infrequently, if ever, directly produced by plants. Paraxanthine has a number of physiological effects on animals. In humans, the compound acts as a nonselective, competitive inhibitor of adenosine receptors. As a result, paraxanthine triggers an elevated diastolic blood pressure and an increase in plasma epinephrine levels. Furthermore, the compound is responsible for the lipolytic properties of caffeine, and its presence in the blood causes an increase in serum free fatty acid concentration. Paraxanthine, unlike caffeine, acts as an enzymatic effector of Na+/K+ ATPase. As a result, it is responsible for increased transport of potassium ions into skeletal muscle tissue. Similarly, the compound also stimulates increases in calcium ion concentration in muscle. Paraxanthine is believed to exhibit a lower toxicity than caffeine. While blood levels commensurate with average intake appear to be fairly innocuous, high blood concentrations of paraxanthine have been linked to spontaneous abortion in pregnant mothers.citation needed 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 References September 2007 Retrieved from http://en..org/wiki/Paraxanthine Categories: Xanthines | StimulantsHidden categories: All articles with statements | Articles with statements since May 2008 | Articles lacking sources from September 2007 | All articles lacking sources 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 日本語 This page was last modified on 30 May 2008, at 19:22
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