Record Information
Version1.0
Creation date2010-04-08 22:06:02 UTC
Update date2018-05-29 00:39:13 UTC
Primary IDFDB003968
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNicotine
DescriptionAlkaloid from Nicotiana tabacum and other Nicotiana subspecies, Asclepias syriaca, Lycopodium subspecies, and other subspecies (Solanaceae, Asclepiadaceae, Crassulaceae). Rare spread of occurrence between angiosperms and cryptogametes (CCD) Nicotine is an alkaloid found in the nightshade family of plants (Solanaceae).
CAS Number54-11-5
Structure
Thumb
Synonyms
SynonymSource
(-)-NicotineChEBI
(-)-3-(1-Methyl-2-pyrrolidyl)pyridineChEBI
(-)-3-(N-Methylpyrrolidino)pyridineChEBI
(R)-3-(1-Methyl-2-pyrrolidinyl)pyridineChEBI
(S)-(-)-NicotineChEBI
(S)-3-(1-Methylpyrrolidin-2-yl)pyridineChEBI
(S)-3-(N-Methylpyrrolidin-2-yl)pyridineChEBI
1-Methyl-2-(3-pyridyl)pyrrolidineChEBI
3-(1-Methyl-2-pyrollidinyl)pyridineChEBI
3-(1-Methylpyrrolidin-2-yl)pyridineChEBI
3-(2-(N-Methylpyrrolidinyl))pyridineChEBI
3-(N-Methylpyrollidino)pyridineChEBI
L(-)-NicotineChEBI
L-3-(1-Methyl-2-pyrrolidyl)pyridineChEBI
L-NicotineChEBI
HabitrolKegg
(S)-NicotineKegg
(+)-NicotineHMDB
(R,S)-NicotineHMDB
1-Methyl-2-(3-pyridal)-pyrrolideneHMDB
1-Methyl-2-(3-pyridal)-pyrrolidineHMDB
1-Methyl-2-(3-pyridiyl)pyrrolidineHMDB
2'-beta-H-NicotineHMDB
3-(1-Methyl-2-pyrrolidinyl)-pyridineHMDB
3-(1-Methyl-2-pyrrolidinyl)pyridineHMDB
3-(N-Methylpyrrolidino)pyridineHMDB
3-N-MethylpyrrolidineHMDB
a -N-MethylpyrrolidineHMDB
a-N-MethylpyrrolidineHMDB
alpha-N-MethylpyrrolidineHMDB
beta-Pyridyl-alpha-N-methylpyrrolidineHMDB
D-NicotineHMDB
delta-NicotineHMDB
DestruxolHMDB
DL-TetrahydronicotyrineHMDB
Fumeto bacHMDB
Methyl-2-pyrrolidinyl)pyridineHMDB
NicodermHMDB
Nicotine polacrilexHMDB
R)-(+)-NicotineHMDB
Tartrate, nicotineHMDB
Nicotine bitartrateHMDB
Nicotine tartrateHMDB
Bitartrate, nicotineHMDB
NicotineChEBI
(S)-3-(1-Methyl-2-pyrrolidinyl)pyridinebiospider
L -1-Methyl-2-[3-pyridyl]pyrrolidinebiospider
L-nicotinebiospider
Pyridine, 3-((2S)-1-methyl-2-pyrrolidinyl)-biospider
Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (S)- (9CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility93.3 g/LALOGPS
logP0.87ALOGPS
logP1.16ChemAxon
logS-0.24ALOGPS
pKa (Strongest Basic)8.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.66 m³·mol⁻¹ChemAxon
Polarizability18.59 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H14N2
IUPAC name3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
InChI IdentifierInChI=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-/m0/s1
InChI KeySNICXCGAKADSCV-JTQLQIEISA-N
Isomeric SMILESCN1CCC[C@H]1C1=CN=CC=C1
Average Molecular Weight162.2316
Monoisotopic Molecular Weight162.115698458
Classification
Description belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyrrolidinylpyridines
Direct ParentPyrrolidinylpyridines
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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 74.04%; H 8.70%; N 17.27%CCD
Melting Point-79 oC
Boiling PointBp 730.5 246.1 °CCD
Experimental Water Solubility1000 mg/mLSEIDELL,A (1941)
Experimental logP1.17HANSCH,C ET AL. (1995)
Experimental pKa3.1
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a] D -166CCD
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-9500000000-f2d4835c504301f9410eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01q9-7900000000-1e2c38b5e4e7aae10d37View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9800000000-fe889308f7088d47c31dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-9500000000-f2d4835c504301f9410eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-4900000000-6d65165a4417a6129eebView 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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-16cdb5f23105be4a892bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-720fe01876c739a30be0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0900000000-85a813588b57acf531feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0900000000-93a3dae1577f4f2dda53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-1900000000-cb6f8cec40dd9ed35d00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00lr-1900000000-1443b1cf22d2de281898View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-440798524836a27b78b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01q9-0900000000-926940dd7f4851dbd73bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00lr-0900000000-6bccc06d40ab273cf972View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-bf73c660c9fef052a3e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-317ad58e8bc4c3092420View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-9400000000-ea4895202e26a55d8a9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ed813017157d07798ea2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1900000000-02ba66ba693d048f19abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-442e757e1da476d883afView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9400000000-47a036aa305825218fa2View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID80863
ChEMBL IDCHEMBL3
KEGG Compound IDC00745
Pubchem Compound ID89594
Pubchem Substance IDNot Available
ChEBI ID17688
Phenol-Explorer IDNot Available
DrugBank IDDB00184
HMDB IDHMDB01934
CRC / DFC (Dictionary of Food Compounds) IDBCM12-J:BCM12-J
EAFUS IDNot Available
Dr. Duke IDNICOTINE
BIGG IDNot Available
KNApSAcK IDC00002057
HET IDNCT
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNicotine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
addictiveDUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anorectic50780 An agent which regulates the physiologic mechanisms that control the appetite and food intake.DUKE
autonomic nervous system paralytic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
autonomic nervous system stimulant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti estrogenic35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti feedantDUKE
anti fumitoryDUKE
cardiovascular38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cholinergic38323 Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons.DUKE
copaminigenic48560 A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.DUKE
ectoparasiticide38956 DUKE
epinephrininergicDUKE
herbicide24527 A substance used to destroy plant pests.DUKE
hyperglycemic76916 A drug which increases the blood glucose level.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
nematistatDUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
serotoninergic48278 DUKE
tranquilizerDUKE
anxiolytic35474 Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.CHEBI
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Nicotine PathwaySMP00431 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).