(2R,3R)-2,3-dihydroxybutanedioic acid; 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine

• ChemBase ID: 175109
• Molecular Formular: C14H20N2O6
• Molecular Mass: 312.3184
• Monoisotopic Mass: 312.13213637
• SMILES: c1ccncc1[C@H]1N(CCC1)C.[C@H]([C@@H](O)C(=O)O)(O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)O)O.CN1CCC[C@H]1c1cccnc1
• InChI: InChI=1S/C10H14N2.C4H6O6/c1-12-7-3-5-10(12)9-4-2-6-11-8-9;5-1(3(7)8)2(6)4(9)10/h2,4,6,8,10H,3,5,7H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t10-;1-,2-/m01/s1
• InChIKey: QLDPCHZQQIASHX-LDGFUSNJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid; 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
• IUPAC Traditional name: L(+)-tartaric acid; nicoderm CQ
• Synonyms: 3-[(2S)-1-Methyl-2-pyrrolidinyl]pyridine (2R,3R)-2,3-Dihydroxybutanedioate; (-)-1-Methyl-2-[3-pyridyl]pyrrolidine Tartrate; Nicotine Tartrate; (-)-Nicotine Bitartrate; Nicotine d-Bitartrate; Nicotine Hydrotartrate; (S)-(-)-Nicotine Mono Tartrate; 3-[(2S)-1-Methyl-2-pyrrolidinyl]pyridine (2R,3R)-2,3-Dihydroxybutanedioate Hydrate; Nicotine Tartrate Dihydrate; (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine (2R,3R)-2,3-Dihydroxybutanedioate Dihydrate; (S)-3-(1-methyl-2-pyrrolidinyl)pyridine [R-(R*,R*)]-2,3-Dihydroxybutanedioate Dihydrate; (-)-Nicotine Di-(+)-Hydrogen Tartrate; S-(-)-Nicotine Ditartrate Dihydrate

Database IDs

• CAS Number: 6019-06-3; 6550-19-2
• PubChem SID: 164231019
• PubChem CID: 21119282

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.9628259
• LogD (pH = 7.4): -0.31012845
• Log P: 1.1625347
• Molar Refractivity: 49.655 cm^3
• Polarizability: 19.449343 Å^3
• Polar Surface Area: 16.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSo; Methanol; Water
• Apperance: Off-White Low Melting Solid; White Solid
• Melting Point: 97-100°C

Safety Information

• Storage Condition: -20°C Freezer; Refrigerator, Under Inert Atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - N417500

Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer. It is a potent neurotoxin.

Toronto Research Chemicals - N412455

Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer. It is a potent neurotoxin.

REFERENCES

• Ferretti, G., et al.: J. Med. Chem., 45, 4724 (2002)
• Guillen, M., et al.: J. Agric. Food Chem., 53, 1093 (2002)
• Ramunno, A., et al.: Bioorg. Med. Chem. Lett., 15, 3237 (2002)
• Alburges, M., et al.: Eur. J. Pharmacol., 573, 124 (2002)
• Ferretti, G., et al.: J. Med. Chem., 45, 4724 (2002)
• Guillen, M., et al.: J. Agric. Food Chem., 53, 1093 (2002)
• Ramunno, A., et al.: Bioorg. Med. Chem. Lett., 15, 3237 (2002)
• Alburges, M., et al.: Eur. J. Pharmacol., 573, 124 (2002)