3-ethynyl-5-[(2S)-1-methylpyrrolidin-2-yl]pyridine

• ChemBase ID: 168783
• Molecular Formular: C12H14N2
• Molecular Mass: 186.25296
• Monoisotopic Mass: 186.11569846
• SMILES: c1(cncc(c1)[C@@H]1CCCN1C)C#C
• Canonical SMILES: C#Cc1cncc(c1)[C@@H]1CCCN1C
• InChI: InChI=1S/C12H14N2/c1-3-10-7-11(9-13-8-10)12-5-4-6-14(12)2/h1,7-9,12H,4-6H2,2H3/t12-/m0/s1
• InChIKey: NUPUDYKEEJNZRG-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethynyl-5-[(2S)-1-methylpyrrolidin-2-yl]pyridine
• IUPAC Traditional name: altinicline
• Synonyms: 3-Ethynyl-5-[(2S)-1-methyl-2-pyrrolidinyl]pyridine; (S)-3-Ethynyl-5-(1-methyl-2-pyrrolidinyl)pyridine; Altinicline; SIB 1508; 5-Ethynyl Nicotine

Database IDs

• CAS Number: 179120-92-4
• PubChem SID: 162262915
• PubChem CID: 3036156

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.527755
• LogD (pH = 7.4): 0.22999732
• Log P: 1.31337
• Molar Refractivity: 54.8273 cm^3
• Polarizability: 22.026854 Å^3
• Polar Surface Area: 16.13 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Pale Yellow Oil

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E932200

5-Ethynylnicotine is an intermediate of nicotinic acetylcholine receptor agonist SIB-1508Y. 5-Ethynylnicotine is used for the treatment of neurological disorders.

REFERENCES

• Pillon, B., et al.: Neurology, 39, 762 (1989)
• Schneider, J., et al.: Brain Res., 519, 122 (1989)
• Cosford, N., et al.: J. Med. Chem., 39, 3235 (1989)
• Sacaan, A., et al.: J. Pharmacol. Exp. Ther., 280, 373 (1989)