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Record Information
Version4.0
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-10-23 19:06:15 UTC
HMDB IDHMDB0014330
Secondary Accession Numbers
  • HMDB14330
Metabolite Identification
Common NameNicotine
DescriptionNicotine is only found in individuals that have used or taken this drug. It is a highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke. [PubChem]Nicotine is a stimulant drug that acts as an agonist at nicotinic acetylcholine receptors. These are ionotropic receptors composed up of five homomeric or heteromeric subunits. In the brain, nicotine binds to nicotinic acetylcholine receptors on dopaminergic neurons in the cortico-limbic pathways. This causes the channel to open and allow conductance of multiple cations including sodium, calcium, and potassium. This leads to depolarization, which activates voltage-gated calcium channels and allows more calcium to enter the axon terminal. Calcium stimulates vesicle trafficking towards the plasma membrane and the release of dopamine into the synapse. Dopamine binding to its receptors is responsible the euphoric and addictive properties of nicotine.Nicotine also binds to nicotinic acetylcholine receptors on the chromaffin cells in the adrenal medulla. Binding opens the ion channel allowing influx of sodium, causing depolarization of the cell, which activates voltage-gated calcium channels. Calcium triggers the release of epinephrine from intracellular vesicles into the bloodstream, which causes vasoconstriction, increased blood pressure, increased heart rate, and increased blood sugar.
Structure
Thumb
Synonyms
ValueSource
(+-)-NicotineChEBI
(+-)-3-(1-Methyl-2-pyrrolidinyl)pyridineChEBI
(R,S)-NicotineChEBI
(RS)-NicotineChEBI
NicotinChEBI
NikotinChEBI
L-NicotineHMDB
Nicotine alkaloidHMDB
Chemical FormulaC10H14N2
Average Molecular Weight162.2316
Monoisotopic Molecular Weight162.115698458
IUPAC Name3-(1-methylpyrrolidin-2-yl)pyridine
Traditional Namenicotine
CAS Registry Number54-11-5
SMILES
CN1CCCC1C1=CN=CC=C1
InChI Identifier
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
InChI KeySNICXCGAKADSCV-UHFFFAOYSA-N
Chemical 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.
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Parenteral:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Gastrointestinal disorders:

    Cardiac disorders:

    General disorders and administration site conditions:

    Psychiatric disorders:

    Vascular disorders:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-79 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility93.3 g/LNot Available
LogP1.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility93.3 g/LALOGPS
logP0.87ALOGPS
logP1.16ChemAxon
logS-0.24ALOGPS
pKa (Strongest Basic)8.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.66 m³·mol⁻¹ChemAxon
Polarizability18.62 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9800000000-e2da519a4fcd1232adadView in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-03di-1900000000-857425bc16c796bf0300View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-7900000000-a874f46eadd0eba440d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-3900000000-e16953a6ae58e6dbf414View 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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Nicotine Metabolism PathwayPw000604Pw000604 greyscalePw000604 simpleNot Available
Nicotine PathwayPw000430Pw000430 greyscalePw000430 simpleNot Available
Displaying all 2 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00184 details
SalivaDetected and Quantified0.00292 +/- 0.0177 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.402 +/- 0.287 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00184 details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)Both
Colorectal adenoma
details
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-6 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-3 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00184
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID917
KEGG Compound IDC16150
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNicotine
METLIN IDNot Available
PubChem Compound942
PDB IDNot Available
ChEBI ID18723
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available