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20-September-2008 09:55:56 - Epiboxidine Epiboxidine IUPAC name 1R,4S,6S-6-3-methyl-5-isoxazolyl- 7-azabicyclo2.2.1heptane Identifiers CAS number 188895-96-7 PubChem 5747670 SMILES CC1=NOC=C1C@H2CC@@H3CCC@H2N3 Properties Molecular formula C10H14N2O Molar mass 178.23 g mol-1 Hazards Main hazards Toxic Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Epiboxidine is a chemical compound which acts as a partial agonist at neural nicotinic acetylcholine receptors, binding to both the α3β4 and the α4β2 subtypes. It was developed as a less toxic analogue of the potent frog-derived alkaloid epibatidine, which is around 200 times stronger than morphine as an analgesic but produces extremely dangerous toxic side effects. Epiboxidine is around ten times less potent than epibatidine as an α4β2 agonist, but has around the same potency as an α3β4 agonist. It has only one-tenth of the analgesic power of epibatidine, but is also much less toxic.1 Uses Despite its decreased potency and toxicity compared to epibatidine, epiboxidine itself is still too toxic to be developed as a drug for use in humans. It is used in scientific research2 and as a parent compound to derive newer analogues which may be safer and have greater potential for clinical development.345 Tablets This pharmacology-related article is a stub. References ^ Badio B, Garraffo HM, Plummer CV, Padgett WL, Daly JW. Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine. European Journal of Pharmacology. 1997 Feb 26;3212:189-94. PMID 9063687 ^ Yan X, Zhao B, Butt CM, Debski EA. Nicotine exposure refines visual map topography through an NMDA receptor-mediated pathway. European Journal of Neuroscience. 2006 Dec;2411:3026-42. PMID 17156364 ^ Fitch RW, Pei XF, Kaneko Y, Gupta T, Shi D, Federova I, Daly JW. Homoepiboxidines: further potent agonists for nicotinic receptors. Bioorganic and Medicinal Chemistry. 2004 Jan 2;121:179-90. PMID 14697783 ^ Cheng J, Izenwasser S, Zhang C, Zhang S, Wade D, Trudell ML. Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo3.2.1octanes. Bioorganic and Medicinal Chemistry Letters. 2004 Apr 5;147:1775-8. PMID 15026069 ^ Armstrong A, Bhonoah Y, Shanahan SE. Aza-Prins-pinacol approach to 7-azabicyclo2.2.1heptanes: syntheses of +/--epibatidine and +/--epiboxidine. Journal of Organic Chemistry. 2007 Oct 12;7221:8019-24. PMID 17867705 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/Epiboxidine Categories: Pharmacology stubs | Analgesics | Nicotinic agonists | Stimulants | Isoxazoles 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 This page was last modified on 27 June 2008, at 01:06
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