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Record Information
Version1.0
Created at2006-08-13 17:16:37 UTC
Updated at2020-09-11 01:33:22 UTC
NP-MRD IDNP0000006
Secondary Accession NumbersNone
Natural Product Identification
Common NameAnabasine
DescriptionAnabasine, also known as (+-)-anabasine or neonicotine, belongs to the class of organic compounds 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. Anabasine is a very strong basic compound (based on its pKa). Anabasine is a potentially toxic compound. A pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3.
Structure
Thumb
Synonyms
ValueSource
(+-)-AnabasineChEBI
NeonicotineHMDB
(+/-)-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
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
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumJSpectraViewer
Species of Origin
SpeciesAnimalia; Plantae
Chemical Taxonomy
Description Belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
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
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)9ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0004350
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023366
KNApSAcK IDC00002015
Chemspider ID21106257
KEGG Compound IDC06180
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnabasine
METLIN ID3283
PubChem Compound2181
PDB IDNot Available
ChEBI ID28986
References
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 ]