(R,S)-Anatabine

(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. CAS Number: 2743-90-0. Synonyms: (±)-Anatabine. Molecular Formula: C10H12N2. Formula Weight: 160.2. Purity: >95%. Formulation: (Request formulation change), A solution in ethanol. Solubility: DMF: 15 mg/ml, DMSO: 15 mg/ml, Ethanol: 50 mg/ml, PBS (pH 7.2): 0.3 mg/ml. lambdamax: 261 nm. SMILES: [C@@H]1(C2=CN=CC=C2)CC=CCN1. InChi Code: InChI=1S/C10H12N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h1-4,6,8,10,12H,5,7H2. InChi Key: SOPPBXUYQGUQHE-UHFFFAOYSA-N.