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20-September-2008 09:55:56 - Synephrine Synephrine Systematic IUPAC name ? Identifiers CAS number 94-07-5 ATC code C01CA08 PubChem 7172 Chemical data Formula C9H13NO2 Mol. mass 167.205 g/mol Pharmacokinetic data Bioavailability ? Metabolism ? Half life ? Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Routes ? Synephrine or oxedrine is a drug aimed at encouraging fat loss. While its effectiveness is widely debated, synephrine has gained significant popularity as an alternative to ephedrine, a related substance which has been made illegal or restricted in many countries due to concerns about potential problems with heart disease risk1 and its use in methamphetamine manufacture. Synephrine is derived primarily from the fruit of Citrus aurantium, a relatively small citrus tree, of which several of its more common names include Bitter Orange, Sour Orange, and Zhi shi. Contents 1 Claims 2 Synephrine is not neosynephrine 3 Associated risks 4 References 5 External links Claims Burns fat Increases energy levels Increases metabolism Promotes weight loss Synephrine is not neosynephrine There has been some confusion surrounding synephrine and phenylephrine neosynephrine, one of its positional isomers. The chemicals are similar in structure; the only difference is the location of the aromatic hydroxyl group. In synephrine, the hydroxyl is at the para position, while in neosynephrine it is at the meta position. Each compound has differing biological properties. Phenylephrine acts primarily on alpha1 adrenergic receptors, so it has mainly vasoconstricting actions. Synephrine's pharmacology has not been thoroughly studied. Some comparisons with octopamine have been performed.2 There is some evidence that it may act at β3.3 Associated risks Many diet products such as Stacker 2 contain synephrine along with caffeine. Some reports have indicated that such diet pills cause numerous harmful effects. The Mayo Clinic published a report that suggested a link between Stacker 2 pills and increased risk of ischemic stroke, increased blood pressure, and cardiac infarcts. Synephrine can also cause arrhythmias 4. It is similar to ephedrine 4 and can therefore show similar symptoms see ephedrine adverse effect. References ^ Jordan S, Murty M, Pilon K October 2004. Products containing bitter orange or synephrine: suspected cardiovascular adverse reactions. CMAJ 171 8: 993-4. PMID 15497209. ^ Brown CM, McGrath JC, Midgley JM, et al February 1988. Activities of octopamine and synephrine stereoisomers on alpha-adrenoceptors. Br. J. Pharmacol. 93 2: 417-29. PMID 2833972. ^ Carpéné C, Galitzky J, Fontana E, Atgié C, Lafontan M, Berlan M April 1999. Selective activation of beta3-adrenoceptors by octopamine: comparative studies in mammalian fat cells. Naunyn Schmiedebergs Arch. Pharmacol. 359 4: 310-21. PMID 10344530. ^ a b Livsmedelsverket Swedish FDA External links Ischemic Stroke Associated With Use of an Ephedra-Free Dietary Supplement Containing Synephrine Mayo Clinic Slim Pickings: Looking Beyond Ephedra New York Times SYNEPHRINE: Is Chih-shih Zhishi Toxic? v d e Adrenergic agonists models/most important in CAPS α α1 METHOXAMINE - Methylnorepinephrine - Oxymetazoline - PHENYLEPHRINE - Metaraminol α2 4-NEMD - CLONIDINE - Guanfacine - Guanabenz - Guanoxabenz - Guanethidine - Xylazine - METHYLDOPA - Apraclonidine - Brimonidine - Detomidine - Dexmedetomidine - Lofexidine - Romifidine - Tizanidine - Xylometazoline Undetermined/ unsorted Amidephrine - Amitraz - Anisodamine - Ergotamine - Indanidine - Medetomidine - Mephentermine - Midodrine - Mivazerol - Naphazoline - Norfenefrine - Octopamine - Phenylpropanolamine - Rilmenidine - Synephrine - Talipexole - Tetrahydrozoline - Xylometazoline β β1 DOBUTAMINE - Dopamine - Denopamine - Xamoterol β2 Short acting β2-agonists: SALBUTAMOL/Levosalbutamol - Fenoterol - TERBUTALINE - Pirbuterol - Procaterol - Bitolterol - Rimiterol - Carbuterol - Tulobuterol - Reproterol - Dopexamine Long acting β2-agonists LABA: Arformoterol - Bambuterol - Clenbuterol - Formoterol - Salmeterol Orciprenaline/metaproterenol - Ritodrine - Hexoprenaline - Indacaterol β3 Amibegron - Solabegron Undetermined/ unsorted Arbutamine - Befunolol - Isoxsuprine - Nylidrin - Oxyfedrine - Prenalterol - Ractopamine - Bromoacetylalprenololmenthane - Broxaterol - Cimaterol - Higenamine - Mabuterol - Methoxyphenamine - Tretoquinol - Zinterol Nonselective β ISOPRENALINE/ISOPROTERENOL α and β Epinephrine α1+2, β1+2 - Norepinephrine α1+2, β1 - Cirazoline - Etilefrine Indirect/ mixed Indirect presynaptic norepinephrine release: Amphetamine - Tyramine Mixed: Ephedrine - Pseudoephedrine Cocaine see also monoamine oxidase inhibitor 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 Cardiac stimulants excluding cardiac glycosides C01C Adrenergic and dopaminergic agents Adrenergic agonists primarily β1 and mixed EPINEPHRINE Etilefrine Isoprenaline Norepinephrine Norfenefrine Phenylephrine Dobutamine Oxedrine Metaraminol Methoxamine Mephentermine Prenalterol Midodrine Arbutamine Dopamine agonists DOPAMINE Fenoldopam Both Dopexamine Ibopamine Octopamine Unknown/ungrouped Dimetofrine Gepefrine Cafedrine Theodrenaline Phosphodiesterase inhibitors PDE3I Amrinone Milrinone Enoximone Bucladesine Other cardiac stimulants Angiotensinamide Xamoterol Levosimendan Retrieved from http://en..org/wiki/Synephrine Categories: Phenethylamines 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 Polski 中文 This page was last modified on 22 July 2008, at 18:34
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