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Record Information
Version1.0
Created at2006-08-13 17:16:37 UTC
Updated at2021-08-19 20:22:27 UTC
NP-MRD IDNP0000006
Secondary Accession NumbersNone
Natural Product Identification
Common NameAnabasine
DescriptionAnabasine is a pyridine and piperidine alkaloid found in the Tree Tobacco (Nicotiana glauca) plant, a close relative of the common tobacco plant (Nicotiana tabacum). It is a structural isomer of, and chemically similar to, nicotine. Its principal (historical) industrial use is as an insecticide. Anabasine 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.
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, MeSH
NeonikotinHMDB
S-(-)-AnabasineHMDB
Chemical FormulaC10H14N2
Average Mass162.2316 Da
Monoisotopic Mass162.11570 Da
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 TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Mb12021-08-14View Spectrum
Species
Species of Origin
Species NameSourceReference
Alangium chinenseKNApSAcK Database
Alangium chinense var.pauciflorum.KNApSAcK Database
Alangium kurziiKNApSAcK Database
Alangium platanifoliumKNApSAcK Database
Alangium salviifoliumKNApSAcK Database
Anabasis aphyllaKNApSAcK Database
Cyphanthera spinescensKNApSAcK Database
Duboisia myoporoidesKNApSAcK Database
Leontice albertiiKNApSAcK Database
Lupinus formosusKNApSAcK Database
Nicotiana acaulisKNApSAcK Database
Nicotiana acuminataKNApSAcK Database
Nicotiana africanaKNApSAcK Database
Nicotiana alataKNApSAcK Database
Nicotiana ameghinoiKNApSAcK Database
Nicotiana amplexicaulisKNApSAcK Database
Nicotiana arentsiiKNApSAcK Database
Nicotiana attenuataKNApSAcK Database
Nicotiana benavidesiiKNApSAcK Database
Nicotiana benthamianaKNApSAcK Database
Nicotiana bigeloviiKNApSAcK Database
Nicotiana bonariensisKNApSAcK Database
Nicotiana cavicolaKNApSAcK Database
Nicotiana clevelandiiKNApSAcK Database
Nicotiana cordifoliaKNApSAcK Database
Nicotiana corymbosaKNApSAcK Database
Nicotiana debneyiKNApSAcK Database
Nicotiana excelsiorKNApSAcK Database
Nicotiana exiguaKNApSAcK Database
Nicotiana forgetianaKNApSAcK Database
Nicotiana fragransKNApSAcK Database
Nicotiana glaucaKNApSAcK Database
Nicotiana glutinosaKNApSAcK Database
Nicotiana goodspeediiKNApSAcK Database
Nicotiana gosseiKNApSAcK Database
Nicotiana hesperisKNApSAcK Database
Nicotiana ingulbaKNApSAcK Database
Nicotiana kawakamiiKNApSAcK Database
Nicotiana knightianaKNApSAcK Database
Nicotiana langsdorffiiKNApSAcK Database
Nicotiana linearisKNApSAcK Database
Nicotiana longibracteataKNApSAcK Database
Nicotiana longifloraKNApSAcK Database
Nicotiana maritimaKNApSAcK Database
Nicotiana megalosiphonKNApSAcK Database
Nicotiana miersiiKNApSAcK Database
Nicotiana nesophilaKNApSAcK Database
Nicotiana noctifloraKNApSAcK Database
Nicotiana nudicaulisKNApSAcK Database
Nicotiana occidentalisKNApSAcK Database
Nicotiana otophoraKNApSAcK Database
Nicotiana paniculataKNApSAcK Database
Nicotiana paucifloraKNApSAcK Database
Nicotiana petunioidesKNApSAcK Database
Nicotiana plumbaginifoliaKNApSAcK Database
Nicotiana raimondiiKNApSAcK Database
Nicotiana repandaKNApSAcK Database
Nicotiana rosulataKNApSAcK Database
Nicotiana rotundifoliaKNApSAcK Database
Nicotiana rusticaKNApSAcK Database
Nicotiana setchelliiKNApSAcK Database
Nicotiana simulansKNApSAcK Database
Nicotiana solanifoliaKNApSAcK Database
Nicotiana spegazziniiKNApSAcK Database
Nicotiana stocktoniiKNApSAcK Database
Nicotiana suaveolensKNApSAcK Database
Nicotiana sylvestrisKNApSAcK Database
Nicotiana tabacum (L.)KNApSAcK Database
Nicotiana thyrosifloraKNApSAcK Database
Nicotiana tobacumKNApSAcK Database
Nicotiana tomentosaKNApSAcK Database
Nicotiana tomentosiformisKNApSAcK Database
Nicotiana trigonophyllaKNApSAcK Database
Nicotiana undulataKNApSAcK Database
Nicotiana velutinaKNApSAcK Database
Nicotiana wigandioidesKNApSAcK Database
Priestleya tomentosaKNApSAcK Database
Spartidium saharaeKNApSAcK Database
Verbascum songoricumKNApSAcK Database
Zinnia elegansKNApSAcK Database
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 Point271.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
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
External Links
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
Good Scents IDrw1135601
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 ]
  4. Rauramo L, Lagerspetz K, Engblom P, Punnonen R: The effect of castration and peroral estrogen therapy on some psychological functions. Front Horm Res. 1975;3:94-104. doi: 10.1159/000398269. [PubMed:1234567 ]
  5. Levin ED, Hao I, Burke DA, Cauley M, Hall BJ, Rezvani AH: Effects of tobacco smoke constituents, anabasine and anatabine, on memory and attention in female rats. J Psychopharmacol. 2014 Oct;28(10):915-22. doi: 10.1177/0269881114543721. Epub 2014 Aug 13. [PubMed:25122040 ]
  6. Keeler RF, Balls LD, Panter K: Teratogenic effects of Nicotiana glauca and concentration of anabasine, the suspect teratogen in plant parts. Cornell Vet. 1981 Jan;71(1):47-53. [PubMed:7226846 ]