(R)-Nicotine

HCID 157672

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Basic information

CAS: 25162-00-9
Standard SMILES: CN1CCC[C@@H]1c1cccnc1
InChIKey: SNICXCGAKADSCV-SNVBAGLBSA-N
Molecular formula: C10H14N2
Average molar mass: 162.23 g/mol
Monoisotopic mass: 162.11569845

Overview

(R)-nicotine is a 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has R-configuration. It is a conjugate base of a (R)-nicotinium(1+). It is an enantiomer of a (S)-nicotine.

Names & identifiers

Preferred name: (R)-Nicotine
IUPAC: 3-[(2R)-1-methylpyrrolidin-2-yl]pyridine
English name: (+)-NICOTINE-(+)-DI-P-TOLUOYL TARTRATE
Molecular formula: C10H14N2
Molecular weight: 162.23

Names & synonyms

(+)-NicotineD-Nicotine(R)-nicotine3-[(2R)-1-methylpyrrolidin-2-yl]pyridine2'-beta-H-NicotineNicotine, (+)-Pyridine, 3-[(2R)-1-methyl-2-pyrrolidinyl]-(R)-3-(1-Methyl-2-pyrrolidinyl)pyridineD-(+)-Nicotine(R)-(+)-NicotineDTXSID0046351(R)-3-(1-Methylpyrrolidin-2-yl)pyridine

Show more names

2'βH-NicotinePseudonicotineR-(R)-Nicotine2’-beta-h-nicotine2'bH-Nicotine (8CI)(+)-NICOTINE-(+)-DI-P-TOLUOYL TARTRATE

UNII-42XNU684Z1BRN 466624342XNU684Z1Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (R)-2'.BETA.H-NICOTINEDTXCID8026351CHEBI:391625-23-06-00064 (Beilstein Handbook Reference)

Database identifiers

CAS: 25162-00-9
PubChem CID: 157672
DTXSID: DTXSID0046351
ChEMBL: CHEMBL9732
ChEBI: CHEBI:39162
UNII: 42XNU684Z1
Nikkaji: J358.868H

Properties

Computed structural properties

XLogP: 1.2
Topological polar surface area: 16.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 12
Formal charge: 0
Complexity: 147

Physicochemical properties

Boiling point: 60 · 60-65°C/0.1mmHg
storage temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
solubility: Chloroform (Slightly), Isopropanol (Slightly), Methanol (Slightly)
form: Oil
Density: 1.032 · 1.032±0.06 g/cm3(Predicted)
pka: 8 · 8.00±0.50(Predicted)
color: Colourless to Brown
Stability: Hygroscopic
InChI: InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m1/s1
InChIKey: SNICXCGAKADSCV-SNVBAGLBSA-N
SMILES: C1=NC=CC=C1[C@H]1CCCN1C
FDA UNII: 42 XNU684Z1 · 42XNU684Z1