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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 17:16:37 UTC
Update Date2017-10-23 19:04:11 UTC
HMDB IDHMDB0004350
Secondary Accession Numbers
  • HMDB04350
Metabolite Identification
Common NameAnabasine
DescriptionAnabasine is a nicotinic receptor agonist toxin and Cholinesterase inhibitor which acts upon the nicotinic acetylcholine receptors. Anabasine is an unstable yellow liquid which is succeptable to light, heat and moisture. It's decomposition products include Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases and carbon dioxide. Anabasine is a pyridine alkaloid found in the stem of the (Nicotiana glauca) plant, a close relative of (Nicotiana tabacum) the common tobacco plant. Anabasine is a metabolite of nicotine which can be used as an indicator of a person's exposure to tobbacco smoke. A piperidine botanical insecticide.
Structure
Thumb
Synonyms
ValueSource
(+-)-AnabasineChEBI
(+/-)-anabasineHMDB
(-)-2-(3'-Pyridyl)piperidineHMDB
(-)-AnabasineHMDB
(S)-3-(2-Piperidinyl)pyridineHMDB
2-(3'-Pyridyl) piperidineHMDB
2-(3-Pyridinyl)piperidineHMDB
3-(2-Piperidinyl)pyridineHMDB
AnabasinHMDB
AnabazinHMDB
DL-AnabasineHMDB
L-3-(2'-Piperidyl)pyridineHMDB
NeonicotineHMDB
NeonikotinHMDB
S-(-)-AnabasineHMDB
Chemical FormulaC10H14N2
Average Molecular Weight162.2316
Monoisotopic Molecular Weight162.115698458
IUPAC Name3-(piperidin-2-yl)pyridine
Traditional Nameanabasine
CAS Registry Number13078-04-1
SMILES
C1CCC(NC1)C1=CN=CC=C1
InChI Identifier
InChI=1S/C10H14N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h3-4,6,8,10,12H,1-2,5,7H2
InChI KeyMTXSIJUGVMTTMU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • Aralkylamine
  • Pyridine
  • Piperidine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

  Biological:

    Plant:

Route of exposure:

  Parenteral:

  Enteral:

Role

Industrial application:

Biological role:

Indirect biological role:

Environmental role:

Physiological effect

Health effect:

  Health condition:

    Psychiatric disorders:

    Gastrointestinal disorders:

    Nervous system disorders:

    Cardiac disorders:

    General disorders and administration site conditions:

    Musculoskeletal and connective tissue disorders:

    Metabolism and nutrition disorders:

    Vascular disorders:

  Observation:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 25 °CNot Available
LogP0.97HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility9.9 g/LALOGPS
logP0.9ALOGPS
logP1.22ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)9.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.96 m³·mol⁻¹ChemAxon
Polarizability18.71 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 - GC-MS (Non-derivatized)splash10-053r-7900000000-88d33f807290f3bd7e7cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-053r-7900000000-88d33f807290f3bd7e7cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-1900000000-bf7a9e9e5bdeacb57bbbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0kml-2910000000-8998ca2fea262a4021ceView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1900000000-18b71ad7bc52e379dacbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-5a686c662d6e37ef9d11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-d94f02a74cab1b211399View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-9300000000-2b092796296acf051347View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-d98806e1a4faa4246128View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2900000000-ba5523c7fa5f41235683View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9600000000-8c76b42506e94084b3e2View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0031 (0.0000-0.0123) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.4 (3.6-5.4) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.10 (0.004-0.20) umol/mmol creatinineAdult (>18 years old)BothActive tobacco user details
Associated Disorders and Diseases
Disease References
Smoking
  1. Moyer TP, Charlson JR, Enger RJ, Dale LC, Ebbert JO, Schroeder DR, Hurt RD: Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. Clin Chem. 2002 Sep;48(9):1460-71. [PubMed:12194923 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023366
KNApSAcK IDNot Available
Chemspider ID21106257
KEGG Compound IDC06180
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnabasine
METLIN ID3283
PubChem Compound2181
PDB IDNot Available
ChEBI ID28986
References
Synthesis ReferenceHasse, K.; Berg, P. Formation of anabasine from cadaverine in the presence of plant extracts. Biochemische Zeitschrift (1959), 331 349-55.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Moyer TP, Charlson JR, Enger RJ, Dale LC, Ebbert JO, Schroeder DR, Hurt RD: Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. Clin Chem. 2002 Sep;48(9):1460-71. [PubMed:12194923 ]
  2. Xu X, Iba MM, Weisel CP: Simultaneous and sensitive measurement of anabasine, nicotine, and nicotine metabolites in human urine by liquid chromatography-tandem mass spectrometry. Clin Chem. 2004 Dec;50(12):2323-30. Epub 2004 Oct 7. [PubMed:15472033 ]
  3. Mizrachi N, Levy S, Goren ZQ: Fatal poisoning from Nicotiana glauca leaves: identification of anabasine by gas-chromatography/mass spectrometry. J Forensic Sci. 2000 May;45(3):736-41. [PubMed:10855991 ]