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20-September-2008 09:55:56 - LR-5182 LR-5182 Systematic IUPAC name 1-7S,8R-8-3,4-dichlorophenyl-7-bicyclo2.2.2octanyl-N,N-dimethylmethanamine Identifiers CAS number 62373-97-1 ATC code ? PubChem 6328354 Chemical data Formula C17H23Cl2N Mol. mass 312.276 g/mol SMILES eMolecules PubChem Pharmacokinetic data Bioavailability ? Metabolism ? Half life ? Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Legal Routes ? LR-5182 is a stimulant drug which acts as a norepinephrine and dopamine reuptake inhibitor, structurally related to the better known drug fencamfamine.123 It was developed by the pharmaceutical company Eli Lilly in the 1970s, and researched for potential use as an antidepressant, although never marketed. LR-5182 has two stereoisomers, both of which are active, although one isomer only blocks reuptake of dopamine and noradrenaline, while the other blocks reuptake of serotonin as well.4 While LR-5182 itself never proceeded beyond initial animal studies, discovery of monoamine reuptake inhibition activity and stimulant effects in drugs of this type has subsequently led to the development of many other stimulant drugs of related chemical structure, primarily developed as potential antidepressants,5 or as substitute drugs for the treatment of cocaine abuse.67 References ^ Wong DT, Bymaster FP. An inhibitor of dopamine uptake, LR5182, cis-3-3,4-dichlorophenyl-2-N,N-dimethylaminomethyl-bicyclo-2,2,2-octane hydrochloride. Life Sciences. 1978, 2310:1041-1047. ^ Fuller RW, Perry KW, Snoddy HD. In vivo effects of LR5182, cis-3-3,4-dichlorophenyl-2-N,N-dimethylaminomethyl-bicyclo-2,2,2-octane hydrochloride, an inhibitor of uptake into dopamine and norepinephrine neurons. Neuropharmacology. 1979, 185:497-501. ^ Wong DT, Bymaster FP, Reid LR. Competitive inhibition of catecholamine uptake in synaptosomes of rat brain by rigid bicyclo-octanes. Journal of Neurochemistry. 1980 Jun;346:1453-8. PMID 7381469 ^ Wedney S, Howard JL, Large BT, Pullar IA. The inhibition of monoamine uptake into rat brain synaptosomes by selected bicyclo-octanes and an analogous bicyclo-octene. Biochemical Pharmacology. 1978, 2724:2907-2909. ^ Axford L, Boot JR, Hotten TM, Keenan M, Martin FM, Milutinovic S, Moore NA, O'Neill MF, Pullar IA, Tupper DE, Van Belle KR, Vivien V. Bicyclo2.2.1heptanes as novel triple re-uptake inhibitors for the treatment of depression. Bioorganic and Medicinal Chemistry Letters. 2003 Oct 6;1319:3277-80. PMID 12951108 ^ Deutsch HM, Collard DM, Zhang L, Burnham KS, Deshpande AK, Holtzman SG, Schweri MM. Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-aminomethyl-3-phenylbicyclo2.2.2- and -2.2.1alkane dopamine uptake inhibitors. Journal of Medicinal Chemistry. 1999 Mar 11;425:882-95. PMID 10072685 ^ Javanmard S, Deutsch HM, Collard DM, Kuhar MJ, Schweri MM. Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-substituted-6-amino-5-phenylbicyclo2.2.2octanes. Journal of Medicinal Chemistry. 1999 Nov 18;4223:4836-43. PMID 10579846 Tablets This pharmacology-related article is a stub. 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/LR-5182 Categories: Pharmacology stubs | Stimulants | Dopamine reuptake inhibitors 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 1 June 2008, at 00:24
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