Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120229
Identification
Name: (S)-nicotine
Description:The conjugate acid of (S)-nicotine arising from selective protonation of the tertiary amino group; major species at pH 7.3.
Structure
Thumb
Synonyms:
  • (S)-nicotine
  • (S)-nicotinium cation
Chemical Formula: C10H15N2
Average Molecular Weight: 163.242
Monoisotopic Molecular Weight: 163.12352
InChI Key: SNICXCGAKADSCV-JTQLQIEISA-O
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/p+1/t10-/m0/s1
CAS number: 54-11-5
IUPAC Name:(2S)-1-methyl-2-(pyridin-3-yl)pyrrolidinium
Traditional IUPAC Name: nicoderm CQ
SMILES:C1(CC[CH]([N+](C)1)C2(C=NC=CC=2))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyrrolidinylpyridines. These are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Pyridines and derivatives
Sub ClassPyrrolidinylpyridines
Direct Parent Pyrrolidinylpyridines
Alternative Parents
Substituents
  • Pyrrolidinylpyridine
  • Alkaloid or derivatives
  • Aralkylamine
  • N-alkylpyrrolidine
  • Heteroaromatic compound
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Liquid
Charge:1
Melting point: -79 °C
Experimental Properties:
PropertyValueReference
Melting Point-79 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP1.17HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility93.3 mg/mLALOGPS
logP0.87ALOGPS
logP1.16ChemAxon
logS-0.24ALOGPS
pKa (Strongest Basic)8.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.66 m3·mol-1ChemAxon
Polarizability18.59 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-001i-9500000000-f2d4835c504301f9410eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-3e7377f36ca2547f4885View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-2900000000-a505fff3a4028a6f0d52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00lr-7900000000-b91a12a16d7688e8679dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-01q9-7900000000-10d401d7ffa1c2cdbd9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-0900000000-440798524836a27b78b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-01q9-0900000000-926940dd7f4851dbd73bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00lr-0900000000-6bccc06d40ab273cf972View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0159-2900000000-f7512c405bb662e040a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-7900000000-f1781566be5aee88f6efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-0900000000-09e9b29571abf3a52e44View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9400000000-47a036aa305825218fa2View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
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  • Henningfield JE, Radzius A, Cooper TM, Clayton RR: Drinking coffee and carbonated beverages blocks absorption of nicotine from nicotine polacrilex gum. JAMA. 1990 Sep 26;264(12):1560-4. [2395197 ]
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  • Fallon JH, Keator DB, Mbogori J, Taylor D, Potkin SG: Gender: a major determinant of brain response to nicotine. Int J Neuropsychopharmacol. 2005 Mar;8(1):17-26. Epub 2004 Dec 6. [15579215 ]
  • Metz-Favre C, Donnay C, de Blay F: [Markers of environmental tobacco smoke (ETS) exposure] Rev Mal Respir. 2005 Feb;22(1 Pt 1):81-92. [15968761 ]
  • Fontaine B: [Smoking and breastfeeding: how can we help mothers stop smoking?] J Gynecol Obstet Biol Reprod (Paris). 2005 Apr;34 Spec No 1:3S209-12. [15980790 ]
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  • Miksys S, Tyndale RF: Nicotine induces brain CYP enzymes: relevance to Parkinson's disease. J Neural Transm Suppl. 2006;(70):177-80. [17017527 ]
  • Katsura M, Ohkuma S: Functional proteins involved in regulation of intracellular Ca(2+) for drug development: chronic nicotine treatment upregulates L-type high voltage-gated calcium channels. J Pharmacol Sci. 2005 Mar;97(3):344-7. Epub 2005 Mar 12. [15764844 ]
  • Ziegler UE, Kauczok J, Dietz UA, Reith HB, Schmidt K: Clinical correlation between the consumption of nicotine and cotinine concentrations in urine and serum by competitive enzyme-linked immunosorbent assay. Pharmacology. 2004 Dec;72(4):254-9. [15539886 ]
  • Tanaka H, Tanabe N, Shoji M, Suzuki N, Katono T, Sato S, Motohashi M, Maeno M: Nicotine and lipopolysaccharide stimulate the formation of osteoclast-like cells by increasing macrophage colony-stimulating factor and prostaglandin E2 production by osteoblasts. Life Sci. 2006 Mar 6;78(15):1733-40. Epub 2005 Nov 2. [16266722 ]
  • Gutala R, Wang J, Hwang YY, Haq R, Li MD: Nicotine modulates expression of amyloid precursor protein and amyloid precursor-like protein 2 in mouse brain and in SH-SY5Y neuroblastoma cells. Brain Res. 2006 Jun 6;1093(1):12-9. Epub 2006 May 16. [16707114 ]
  • Tanabe J, Tregellas JR, Martin LF, Freedman R: Effects of nicotine on hippocampal and cingulate activity during smooth pursuit eye movement in schizophrenia. Biol Psychiatry. 2006 Apr 15;59(8):754-61. Epub 2005 Nov 2. [16259965 ]
  • de Leon J, Dadvand M, Canuso C, White AO, Stanilla JK, Simpson GM: Schizophrenia and smoking: an epidemiological survey in a state hospital. Am J Psychiatry. 1995 Mar;152(3):453-5. [7864277 ]
  • de Leon J, Tracy J, McCann E, McGrory A, Diaz FJ: Schizophrenia and tobacco smoking: a replication study in another US psychiatric hospital. Schizophr Res. 2002 Jul 1;56(1-2):55-65. [12084420 ]
  • Aguilar MC, Gurpegui M, Diaz FJ, de Leon J: Nicotine dependence and symptoms in schizophrenia: naturalistic study of complex interactions. Br J Psychiatry. 2005 Mar;186:215-21. [15738502 ]
  • Nolley EP, Kelley BM: Adolescent reward system perseveration due to nicotine: studies with methylphenidate. Neurotoxicol Teratol. 2007 Jan-Feb;29(1):47-56. Epub 2006 Oct 4. [17129706 ]
Synthesis Reference: Breuer E; Melumad D A one-step synthesis of nicotine from cyclopropyl 3-pyridyl ketone. Tetrahedron letters (1969), 41 3595-6.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
HMDBHMDB01934
CHEMSPIDER5294163
CHEBI59806
PUBCHEM6919000
LIGAND-CPDC00745
NCI5065