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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N2
Molecular Weight 162.2316
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANABASINE

SMILES

C1CC[C@H](NC1)C2=CC=CN=C2

InChI

InChIKey=MTXSIJUGVMTTMU-JTQLQIEISA-N
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/t10-/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H14N2
Molecular Weight 162.2316
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Anabasine, a tobacco alkaloid, was used as a biomarker of active tobacco use. Anabasine is a selective alpha7-nicotinic acetylcholine receptor agonist. Anabasine antagonized MK-801-elicited mouse popping behavior, an animal model of schizophrenia.

Approval Year

PubMed

PubMed

TitleDatePubMed
Nicotine's defensive function in nature.
2004 Aug
Anabasine, a selective nicotinic acetylcholine receptor agonist, antagonizes MK-801-elicited mouse popping behavior, an animal model of schizophrenia.
2004 Aug 31
Simultaneous and sensitive measurement of anabasine, nicotine, and nicotine metabolites in human urine by liquid chromatography-tandem mass spectrometry.
2004 Dec
Quantitative structure-activity relationship study using refractotopological state atom index on some neonicotinoid insecticides.
2004 Dec 1
On-line screening of conformationally constrained nicotines and anabasines for agonist activity at the alpha3beta4- and alpha4beta2-nicotinic acetylcholine receptors using immobilized receptor-based liquid chromatographic stationary phases.
2004 Dec 25
Coaxing a pyridine nucleus to give up its aromaticity: synthesis and pharmacological characterization of novel conformationally restricted analogues of nicotine and anabasine.
2004 Dec 30
Structural diversity and defensive properties of norditerpenoid alkaloids.
2004 Jul
The structural basis for GTS-21 selectivity between human and rat nicotinic alpha7 receptors.
2004 Jul
[Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin].
2004 Jul-Aug
Residential treatment for smokeless tobacco use: a case series.
2004 Jun
Comparative analysis of neonicotinoid binding to insect membranes: II. An unusual high affinity site for [3H]thiamethoxam in Myzus persicae and Aphis craccivora.
2004 Oct
Comparative analysis of neonicotinoid binding to insect membranes: I. A structure-activity study of the mode of [3H]imidacloprid displacement in Myzus persicae and Aphis craccivora.
2004 Oct
[Biomarkers of tobacco smoke].
2005
[What are the markers of tobacco smoking?].
2005 Apr
Stereoselectivity of the demethylation of nicotine piperidine homologues by Nicotiana plumbaginifolia cell suspension cultures.
2005 Aug
Neonicotinoids show selective and diverse actions on their nicotinic receptor targets: electrophysiology, molecular biology, and receptor modeling studies.
2005 Aug
Feeding responses of free-flying honeybees to secondary compounds mimicking floral nectars.
2005 Dec
Identification of aldehyde oxidase as the neonicotinoid nitroreductase.
2005 Feb
Acute and subacute effects of tobacco alkaloids, tobacco-specific nitrosamines and phenethyl isothiocyanate on N'-nitrosonornicotine metabolism in rats.
2005 Nov 15
Rhesus monkey alpha7 nicotinic acetylcholine receptors: comparisons to human alpha7 receptors expressed in Xenopus oocytes.
2005 Nov 7
A general procedure for the enantioselective synthesis of the minor tobacco alkaloids nornicotine, anabasine, and anatabine.
2005 Oct 31
Smoking and reproduction: the oviduct as a target of cigarette smoke.
2005 Sep 28
Cytisine for smoking cessation: a literature review and a meta-analysis.
2006 Aug 14-28
Specific detection of anabasine, nicotine, and nicotine metabolites in urine by liquid chromatography-tandem mass spectrometry.
2006 Dec
Influence of agonists and antagonists on the segmental motion of residues near the agonist binding pocket of the acetylcholine-binding protein.
2006 Dec 22
Substrate specificity of rabbit aldehyde oxidase for nitroguanidine and nitromethylene neonicotinoid insecticides.
2006 Jan
Assignment of absolute configuration of cyclic secondary amines by NMR techniques using Mosher's method: a general procedure exemplified with (-)-isoanabasine.
2006 Jan
Resistance and cross-resistance to neonicotinoid insecticides and spinosad in the Colorado potato beetle, Leptinotarsa decemlineata (Say) (Coleoptera: Chrysomelidae).
2006 Jan
[Analogs of anabasine as reversible and irreversible inhibitors of choline esterases of different animals].
2006 Jan-Feb
Chloropyridinyl neonicotinoid insecticides: diverse molecular substituents contribute to facile metabolism in mice.
2006 Jul
Role in the selectivity of neonicotinoids of insect-specific basic residues in loop D of the nicotinic acetylcholine receptor agonist binding site.
2006 Oct
Anabasine toxicity from a topical folk remedy.
2006 Sep
Characterisation of nicotine and related compounds using electrospray ionisation with ion trap mass spectrometry and with quadrupole time-of-flight mass spectrometry and their detection by liquid chromatography/electrospray ionisation mass spectrometry.
2007
Effect of anabasine on catecholamine secretion from the perfused rat adrenal medulla.
2007 Dec
Nicotine lozenges for the treatment of smokeless tobacco use.
2007 Feb
Reversal of agonist selectivity by mutations of conserved amino acids in the binding site of nicotinic acetylcholine receptors.
2007 Feb 23
Insecticidal and neuroblocking potencies of variants of the imidazolidine moiety of imidacloprid-related neonicotinoids and the relationship to partition coefficient and charge density on the pharmacophore.
2007 Feb 7
Synthesis, insecticidal activity, and QSAR of novel nitromethylene neonicotinoids with tetrahydropyridine fixed cis configuration and exo-ring ether modification.
2007 Mar 21
The effect of the cholinergic anti-inflammatory pathway on experimental colitis.
2007 Nov
Blocking actions of alkylene-tethered bis-neonicotinoids on nicotinic acetylcholine receptors expressed by terminal abdominal ganglion neurons of Periplaneta americana.
2007 Oct 2
Analyses of tobacco alkaloids by cation-selective exhaustive injection sweeping microemulsion electrokinetic chromatography.
2007 Sep 14
The fetal cleft palate: v. elucidation of the mechanism of palatal clefting in the congenital caprine model.
2008 Apr
Enantiomeric analysis of anatabine, nornicotine and anabasine in commercial tobacco by multi-dimensional gas chromatography and mass spectrometry.
2008 Apr 1
Modulation of spontaneous hippocampal synaptic events with 5-hydroxyindole, 4OH-GTS-21, and rAAV-mediated alpha7 nicotinic receptor gene transfer.
2008 Apr 8
Role of nicotinic and estrogen signaling during experimental acute and chronic bladder inflammation.
2008 Jan
Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine.
2008 Jan 9
Sequential preconcentration by coupling of field amplified sample injection with pseudo isotachophoresis-acid stacking for analysis of alkaloids in capillary electrophoresis.
2008 Mar
Synthesis of 2-(pyridin-3-yl)-1-azabicyclo[3.2.2]nonane, 2-(pyridin-3-yl)-1-azabicyclo[2.2.2]octane, and 2-(pyridin-3-yl)-1-azabicyclo[3.2.1]octane, a class of potent nicotinic acetylcholine receptor-ligands.
2008 May 2
Screening of tobacco smoke condensate for nicotinic acetylcholine receptor ligands using cellular membrane affinity chromatography columns and missing peak chromatography.
2008 Sep 29
Separation and measurement of plant alkaloid enantiomers by RP-HPLC analysis of their Fmoc-Alanine analogs.
2008 Sep-Oct
Patents

Patents

Sample Use Guides

Goats: Different, single doses of anabasine, anabaseine, epibatidine, DMPP, or saline control were administered I.V. to pregnant goats on day 40 of gestation and the number of fetal movements per 5 min sample was measured by ultrasound at times 0, 0.5, 1, 2, 4 and 8 h. The differences among does in fetal movements were more consistent at dosing and following recovery for doses of anabasine above 0.125 mg/kg compared to the other compounds and dosages. Anabasine actions were dose-dependent with an IC50 value of ∼0.1 mg/kg, and, at a dose of 0.8 mg/kg, completely inhibited fetal movement for 1.5 h after dosing.
Route of Administration: Intravenous
In Vitro Use Guide
Curator's Comment: When employed at a concentration of 100 uM, anabasine inhibited ACTH-stimulated aldosterone synthesis by 44%. https://www.ncbi.nlm.nih.gov/pubmed/8156919
The effects of anabasine on aromatase in placental microsomes was assessed in tissue obtained from two women. In these two experiments the apparent Ki`s for anabasine inhibition of aromatase were 2 and 3 uM.
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:24:20 UTC 2023
Edited
by admin
on Thu Jul 06 02:24:20 UTC 2023
Record UNII
LMS11II2LO
Record Status Validated (UNII)
Record Version
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Name Type Language
ANABASINE
HSDB   MI   WHO-DD  
Common Name English
NICOTINE RESINATE IMPURITY G [EP IMPURITY]
Common Name English
(S)-ANABASINE
Common Name English
ANABASINE [MI]
Common Name English
(S)-(-)-ANABASINE
Common Name English
NICOTINE IMPURITY G [EP IMPURITY]
Common Name English
PYRIDINE, 3-(2S)-2-PIPERIDINYL-
Systematic Name English
(2S)-2-(PYRIDIN-3-YL)PIPERIDINE
Systematic Name English
3-(2-PIPERIDINYL)PYRIDINE
Systematic Name English
L-3-(2'-PIPERIDYL)PYRIDINE
Common Name English
NICOTINE RELATED COMPOUND G [USP IMPURITY]
Common Name English
NSC-87504
Code English
ANABASIN
Common Name English
NEONICOTINE
Common Name English
PYRIDINE, 3-(2-PIPERIDINYL)-, (S)-
Common Name English
NEONIKOTIN
Common Name English
NICOTINE RELATED COMPOUND G [USP-RS]
Common Name English
(-)-2-(3'-PYRIDYL)PIPERIDINE
Common Name English
Anabasine [WHO-DD]
Common Name English
2-(3-PYRIDYL)PIPERIDINE
Systematic Name English
(-)-ANABASINE
Common Name English
ANABASINE [HSDB]
Common Name English
NICOTINE DITARTRATE DIHYDRATE IMPURITY G [EP IMPURITY]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C737
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
EPA PESTICIDE CODE 6001
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
NCI_THESAURUS C221
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
Code System Code Type Description
MESH
D000691
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-791-3
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
CHEBI
28986
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
FDA UNII
LMS11II2LO
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
PUBCHEM
205586
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
ALANWOOD
anabasine
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
RS_ITEM_NUM
1463382
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
WIKIPEDIA
ANABASINE
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
MERCK INDEX
M1882
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY Merck Index
HSDB
3462
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
NCI_THESAURUS
C124073
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
NSC
87504
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
CHEBI
74
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
CAS
494-52-0
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID9041607
Created by admin on Thu Jul 06 02:24:20 UTC 2023 , Edited by admin on Thu Jul 06 02:24:20 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
ANABASINE 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 PRESENT IN TRACE AMOUNTS IN TOBACCO SMOKE, AND CAN BE USED AS AN INDICATOR OF A PERSON'S EXPOSURE TO TOBACCO SMOKE.
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
ANABASINE (ug/cigarette) Canadian = 67.1 SD(9.4) Imported = 63.3 SD(6.5)
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY