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(R,S)-Anatabine is an alkaloid that has been found as a minor component in tobacco (Nicotiana). It is an agonist of alpha4beta2 and alpha6/alpha3beta2beta4 subunit-containing nicotinic acetylcholine receptors (nAChRs, EC50s = 6.1 and 3.6 µM, respectively). It is selective for alpha4beta2 and alpha6/alpha3beta2beta4 subunit-containing nAChRs over alpha3beta4 subunit-containing nAChRs and alpha7 nAChRs (EC50s = 70.6 and 158.5 µM, respectively). (R,S)-Anatabine stimulates dopamine, but not norepinephrine, release from isolated rat brain synaptosomes (EC50s = 1.76 and >100 µM, respectively). It increases the time spent at the top of the tank in a novel tank test, indicating anxiolytic-like activity, in zebrafish when used at a concentration of 10 mg/L. (R,S)-Anatabine (0.05 mg/ml in the drinking water) decreases disease severity in a mouse model of moderate, but not low or severe, experimental autoimmune thyroiditis induced by immunization with thyroglobulin, complete Freund's adjuvant (CFA), and M. tuberculosis. It decreases food and nicotine self-administration in monkeys (ED50s = 2.085 and 0.854 mg/kg, respectively). (R,S)-Anatabine has been used as a biomarker of tobacco use.Formal Name: 1,2,3,6-tetrahydro-2,3'-bipyridine 2,3-dihydroxysuccinate. Synonyms: (±)-Anatabine. Molecular Formula: C10H12O2 . C4H6O6. Formula Weight: 310.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 33 mg/ml, DMSO: 20 mg/ml, Ethanol: 1 mg/ml, PBS (pH 7.2): 10 mg/ml. lambdamax: 260 nm. SMILES: OC(C(O)C(O)=O)C(O)=O.C1(C2=CN=CC=C2)CC=CCN1. InChi Code: InChI=1S/C10H12N2.C4H6O6/c1-2-7-12-10(5-1)9-4-3-6-11-8-9,5-1(3(7)8)2(6)4(9)10/h1-4,6,8,10,12H,5,7H2,1-2,5-6H,(H,7,8)(H,9,10). InChi Key: YNIQLVONLDUCKG-UHFFFAOYSA-N.
This website uses cookies, which are necessary for the technical operation of the website and are always set. Other cookies, which increase the usability of this website, serve for direct advertising or simplify interaction with other websites and social networks, will only be used with your consent.
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