Showing Compound Card for Anatabined (CDB005649)

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Record Information
Version1.0
Created at2020-04-27 16:41:51 UTC
Updated at2021-01-04 18:49:02 UTC
CannabisDB IDCDB005649
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAnatabined
DescriptionAnatabine or (S)-1,2,3,6-Tetrahydro-2,3'-bipyridine is an isomer of bipyridine. It belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Anatabine also belongs to the group of compounds known as bipyridines. Bipyridines are organic compounds containing two pyridine rings linked to each other. Anatabine is a minor alkaloid found in the family of plants known as Solanaceae, which includes tobacco and tomato plants. It can also be found in the urine of smokers and smokeless tobacco users (PMID:8245163 ). Anatabine is thought to be biologically active, and part of plants' natural defense system against insects. This nicotine-related alkaloid is an inhibitor of human cytochrome P-450 2A6 (PMID: 14757175 ). On a biochemical level, anatabine appears to be active against certain nicotinic acetylcholine receptors (PMID: 24490707 ). Anatabine was used as a dietary supplement known as Anatabloc and CigRx until mid 2014. Anatabine is also found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-AnatabineKegg
Chemical FormulaC10H12N2
Average Molecular Weight160.22
Monoisotopic Molecular Weight160.1
IUPAC Name(2S)-1,2,3,6-tetrahydro-2,3'-bipyridine
Traditional Nameanatabine
CAS Registry Number581-49-7
SMILES
C1N[C@@H](CC=C1)C1=CN=CC=C1
InChI Identifier
InChI=1S/C10H12N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h1-4,6,8,10,12H,5,7H2/t10-/m0/s1
InChI KeySOPPBXUYQGUQHE-JTQLQIEISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Pyridine
  • Hydropyridine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point145.5 °CNot Available
Water Solubility1000 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.03ALOGPS
logP1.02ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)8.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.92 m³·mol⁻¹ChemAxon
Polarizability17.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAnatabined, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-07cu-1900000000-83089eec362cad1f93f6Spectrum
Predicted GC-MSAnatabined, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAnatabined, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-972f6de458718e02613b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-1900000000-7baac9dff046273f5a282017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-9200000000-f060db2ea029ecd78a782017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-32258a0e4b3989d0533f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-ffc8f788de93316624242017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-7900000000-cac0a5ea86d517e754112017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-9700000000-4ed7ee7465de65e911002021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9400000000-c2cb4e83d6aa78ce7b112021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-0e0e70179caacf58851b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-ec9dd3a4861a20c6f98c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-d43f6eaf3f1dd72eec342021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-5900000000-19a118d5150f724690502021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0004476
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023374
KNApSAcK IDC00002017
Chemspider ID10910
KEGG Compound IDC10126
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnatabine
METLIN ID7061
PubChem Compound11388
PDB IDNot Available
ChEBI ID2705
References
General References
  1. Jacob P 3rd, Yu L, Liang G, Shulgin AT, Benowitz NL: Gas chromatographic-mass spectrometric method for determination of anabasine, anatabine and other tobacco alkaloids in urine of smokers and smokeless tobacco users. J Chromatogr. 1993 Sep 8;619(1):49-61. doi: 10.1016/0378-4347(93)80445-a. [PubMed:8245163 ]
  2. Denton TT, Zhang X, Cashman JR: Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. Biochem Pharmacol. 2004 Feb 15;67(4):751-6. doi: 10.1016/j.bcp.2003.10.022. [PubMed:14757175 ]
  3. Mello NK, Fivel PA, Kohut SJ, Caine SB: Anatabine significantly decreases nicotine self-administration. Exp Clin Psychopharmacol. 2014 Feb;22(1):1-8. doi: 10.1037/a0035409. [PubMed:24490707 ]