{"Abbreviation":"","Aliases":["1,2,3,6-Tetrahydro-2,3'-bipyridine","2,3'-Bipyridine, 1,2,3,6-tetrahydro-, (S)-","3-((2S)-1,2,3,6-tetrahydropyridin-2-yl)pyridine","2,3'-Bipyridine, 1,2,3,6-tetrahydro-, (2S)-","(2S)-1,2,3,6-tetrahydro-2,3'-bipyridine","starbld0001739","orb1683163","US8609708, 50 Anatabine","FT31535","Nicotine impurity a","HY-126047","CS-0090319","E87376","Nicotine resinate impurity a","Q487291","Nicotine ditartrate dihydrate impurity a"],"Boiling Point":"145.5 °C","CAS":"581-49-7","ChEBI":"CHEBI:2705","ChEMBL":"CHEMBL3640772","ChemicalClasses":["arylalkylamine"],"Chirality":"absolute","Erowid Experience Reports":null,"Esters":[],"Formating":[],"HMDB ID":"HMDB0004476","HeavyAtomCount":12,"IUPACName":"3-[(2S)-1,2,3,6-tetrahydropyridin-2-yl]pyridine","InChI":"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/t10-/m0/s1","InChIKey":"SOPPBXUYQGUQHE-JTQLQIEISA-N","MolecularFormula":"C\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"160.22 g/mol","Opticalactivity":"UNSPECIFIED","Physical Description":"Liquid","PubChemId":11388,"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Anatabine","Name":"Anatabine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/11388","Name":"Anatabine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL3640772","Name":"Anatabine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2705","Name":"Anatabine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=581-49-7","Name":"Anatabine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0004476","Name":"Anatabine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C10126","Name":"Anatabine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/5PP654XB7D","Name":"Anatabine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID901016110","Name":"Anatabine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 11388, Anatabine. Accessed July 19, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/11388\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/11388\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Anatabine. UNII: 5PP654XB7D. Global Substance Registration System. Accessed July 19, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/5PP654XB7D\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/5PP654XB7D\u003c/a\u003e"],"SMILES":"C1C=CCN[C@@H]1C2=CN=CC=C2","SaltData":[{"AcidCount":1,"AmineCount":1,"Formula":"C(C(=O)O)C(CC(=O)O)(C(=O)O)O","Name":"citrate","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 141.594 74.742\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h142v75H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m27.439 17.345-13.2-7.616\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M14.239 9.729 1.038 17.345M14.239 12.544 3.477 18.753\"/\u003e\u003c/g\u003e\u003cpath d=\"M1.038 17.345v15.231M1.038 32.576l10.047 5.797M17.392 38.373l10.047-5.797M27.439 17.345v15.231\" class=\"bond\"/\u003e\u003cpath fill=\"#000\" stroke=\"none\" d=\"m27.615 32.273-.351.607 13.365 9.912v-2.598l2.25-1.298z\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M40.629 40.194v15.232M43.068 41.603v12.415\"/\u003e\u003c/g\u003e\u003cpath d=\"m40.629 55.426 10.047 5.796\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m56.983 61.222 10.047-5.796M55.765 59.11l8.827-5.092\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m56.983 61.222 5.024-2.898M55.765 59.11l4.413-2.546\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"M67.03 55.426V40.194\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m67.03 40.194-13.2-7.615M64.592 41.603 53.83 35.394\"/\u003e\u003c/g\u003e\u003cpath d=\"m40.629 40.194 13.201-7.615\" class=\"bond\"/\u003e\u003cg fill=\"#3050f8\" stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M16.18 42.642h-.721l-2.619-4.066h-.03l.03.595q.024.357.024.732v2.739h-.566v-4.9h.714l2.608 4.055h.03l-.018-.328-.024-.476q-.006-.262-.006-.482v-2.769h.578zM16.043 48.103h-.62v-2.286h-2.512v2.286h-.613v-4.899h.613v2.071h2.512v-2.071h.62z\"/\u003e\u003c/g\u003e\u003cpath fill=\"#3050f8\" stroke=\"none\" d=\"M55.771 65.491h-.721l-2.619-4.066h-.03l.03.596q.024.357.024.732v2.738h-.566v-4.899h.714l2.608 4.054h.03l-.018-.327-.024-.477q-.006-.262-.006-.482v-2.768h.578z\" class=\"atom\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m11.085 38.373-5.023-2.899M17.392 38.373l5.024-2.899M50.676 61.222l-5.023-2.898\" class=\"hi\"/\u003e\u003c/g\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m113.97 48.801-13.198 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M101.991 55.717V67.74M99.553 55.717V67.74\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"M101.991 67.74v-6.012M99.553 67.74v-6.012\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m100.772 56.421-9.922-5.729M113.97 48.801v-15.24M113.97 33.561l-13.198-7.62M100.772 25.941v-15.24\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M99.553 9.997 110.08 3.92M100.772 12.109l10.527-6.078\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m110.08 3.92-5.264 3.038M111.299 6.031l-5.263 3.039\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"M100.772 10.701 90.85 4.972M113.97 33.561l15.009 2.647\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m127.593 35.963 7.701-9.178M129.46 37.53l7.701-9.177\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m135.294 26.785-3.85 4.589M137.161 28.353l-3.851 4.589\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m128.979 36.208 3.846 10.567M113.97 33.561l3.847-10.568\" class=\"bond\"/\u003e\u003cpath stroke=\"none\" d=\"M103.031 71.658q0 .756-.256 1.328-.256.565-.756.881-.5.315-1.244.315-.756 0-1.262-.315-.506-.316-.756-.887-.244-.572-.244-1.334 0-.75.244-1.309.25-.566.756-.881t1.274-.316q.732 0 1.232.316.5.309.756.875.256.565.256 1.327m-3.863 0q0 .923.387 1.459.393.53 1.22.53.84 0 1.221-.53.387-.536.387-1.459 0-.929-.387-1.452-.381-.524-1.209-.524-.833 0-1.226.524-.393.523-.393 1.452\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M89.833 48.798q0 .756-.256 1.328-.256.565-.756.881-.5.315-1.244.315-.756 0-1.262-.315-.506-.316-.756-.887-.244-.572-.244-1.334 0-.75.244-1.309.25-.566.756-.881t1.274-.316q.732 0 1.232.316.5.309.756.875.256.565.256 1.327m-3.863 0q0 .923.387 1.459.393.53 1.22.53.839 0 1.22-.53.387-.536.387-1.459 0-.929-.387-1.452-.381-.524-1.208-.524-.834 0-1.226.524-.393.523-.393 1.452M84.753 51.251h-.619v-2.286h-2.512v2.286h-.613v-4.9h.613v2.072h2.512v-2.072h.619z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"none\" d=\"M116.23 3.078q0 .756-.256 1.328-.256.565-.756.881-.5.315-1.245.315-.756 0-1.262-.315-.506-.316-.756-.887-.244-.572-.244-1.334 0-.75.244-1.309.25-.566.756-.881t1.274-.316q.733 0 1.233.316.5.309.756.875.256.565.256 1.327m-3.864 0q0 .923.387 1.459.393.53 1.22.53.84 0 1.221-.53.387-.536.387-1.459 0-.929-.387-1.452-.381-.524-1.209-.524-.833 0-1.226.524-.393.523-.393 1.452\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M89.833 3.078q0 .756-.256 1.328-.256.565-.756.881-.5.315-1.244.315-.756 0-1.262-.315-.506-.316-.756-.887-.244-.572-.244-1.334 0-.75.244-1.309.25-.566.756-.881T87.589.56q.732 0 1.232.316.5.309.756.875.256.565.256 1.327m-3.863 0q0 .923.387 1.459.393.53 1.22.53.839 0 1.22-.53.387-.536.387-1.459 0-.929-.387-1.452-.381-.524-1.208-.524-.834 0-1.226.524-.393.523-.393 1.452M84.753 5.531h-.619V3.245h-2.512v2.286h-.613v-4.9h.613v2.072h2.512V.631h.619z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"none\" d=\"M141.034 24.53q0 .756-.256 1.328-.256.565-.756.881-.5.315-1.244.315-.756 0-1.262-.315-.506-.316-.756-.887-.244-.572-.244-1.334 0-.75.244-1.31.25-.565.756-.881.506-.315 1.274-.315.732 0 1.232.315.5.31.756.876.256.565.256 1.327m-3.863 0q0 .923.387 1.459.393.529 1.22.529.839 0 1.22-.529.387-.536.387-1.459 0-.929-.387-1.453-.381-.523-1.208-.523-.834 0-1.226.523-.393.524-.393 1.453\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M136.451 50.525q0 .757-.256 1.328-.256.566-.756.881-.501.316-1.245.316-.756 0-1.262-.316-.506-.315-.756-.887-.244-.571-.244-1.333 0-.751.244-1.31.25-.566.756-.881t1.274-.316q.732 0 1.233.316.5.309.756.875.256.565.256 1.327m-3.864 0q0 .923.387 1.459.393.53 1.22.53.84 0 1.221-.53.387-.536.387-1.459 0-.928-.387-1.452-.381-.524-1.209-.524-.833 0-1.226.524t-.393 1.452M140.757 52.978h-.619v-2.286h-2.513v2.286h-.613v-4.899h.613v2.071h2.513v-2.071h.619z\"/\u003e\u003c/g\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M121.442 19.237q0 .756-.256 1.328-.256.565-.756.881-.5.315-1.244.315-.756 0-1.262-.315-.506-.316-.756-.887-.244-.572-.244-1.334 0-.75.244-1.309.25-.566.756-.881t1.274-.316q.732 0 1.232.316.5.309.756.875.256.565.256 1.327m-3.864 0q0 .923.387 1.459.393.53 1.221.53.839 0 1.22-.53.387-.536.387-1.459 0-.928-.387-1.452-.381-.524-1.208-.524-.834 0-1.227.524t-.393 1.452M125.748 21.69h-.619v-2.286h-2.512v2.286h-.613v-4.899h.613v2.071h2.512v-2.071h.619z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m90.85 50.692 4.961 2.864M90.85 50.692l4.961 2.864M90.85 4.972l4.961 2.865M90.85 4.972l4.961 2.865M132.825 46.775l-1.923-5.283M117.817 22.993l-1.924 5.284\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"Anatabine citrate","UNII":"MZE7Y8PB3F"}],"Salts":["citrate"],"Solubility":"1000 mg/mL","StereoisomerData":[],"Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 68.069 57.36\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h69v58H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m27.439 8.654-13.2-7.616\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M14.239 1.038 1.038 8.654M14.239 3.853 3.477 10.062\"/\u003e\u003c/g\u003e\u003cpath d=\"M1.038 8.654v15.231M1.038 23.885l10.047 5.797M17.392 29.682l10.047-5.797M27.439 8.654v15.231\" class=\"bond\"/\u003e\u003cpath fill=\"#000\" stroke=\"none\" d=\"m27.615 23.582-.351.607 13.365 9.912v-2.598l2.25-1.298z\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M40.629 31.503v15.232M43.068 32.912v12.415\"/\u003e\u003c/g\u003e\u003cpath d=\"m40.629 46.735 10.047 5.796\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m56.983 52.531 10.047-5.796M55.765 50.419l8.827-5.092\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m56.983 52.531 5.024-2.898M55.765 50.419l4.413-2.546\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"M67.03 46.735V31.503\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m67.03 31.503-13.2-7.615M64.592 32.912 53.83 26.703\"/\u003e\u003c/g\u003e\u003cpath d=\"m40.629 31.503 13.201-7.615\" class=\"bond\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M16.18 33.951h-.721l-2.619-4.066h-.03l.03.595q.024.357.024.732v2.739h-.566v-4.9h.714l2.608 4.055h.03l-.018-.328-.024-.476q-.006-.262-.006-.482v-2.769h.578zM16.043 39.412h-.62v-2.286h-2.512v2.286h-.613v-4.899h.613v2.071h2.512v-2.071h.62z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"none\" d=\"M55.771 56.8h-.721l-2.619-4.066h-.03l.03.596q.024.357.024.732V56.8h-.566v-4.899h.714l2.608 4.054h.03l-.018-.327-.024-.477q-.006-.262-.006-.482v-2.768h.578z\" class=\"atom\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m11.085 29.682-5.023-2.898M17.392 29.682l5.024-2.898M50.676 52.531l-5.023-2.898\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"Anatabine","UNII":"5PP654XB7D","Wikipedia":"Anatabine","XLogP":0.9}