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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=CN=CC=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
Benzylidene analogs of anabaseine display partial agonist and antagonist properties at the mouse 5-hydroxytryptamine(3A) receptor.
2001 Dec
Insecticidal and neural activities of candidate photoaffinity probes for neonicotinoid binding sites.
2001 Jul
Anabasine and anatabine as biomarkers for tobacco use during nicotine replacement therapy.
2002 Dec
Translocation and translaminar bioavailability of two neonicotinoid insecticides after foliar application to cabbage and cotton.
2002 Jan
Quantitative structure-activity relationship study on some azidopyridinyl neonicotinoid insecticides for their selective affinity towards the drosophila nicotinic receptor over mammalian alpha4beta2 receptor using electrotopological state atom index.
2003
Novaluron (Rimon), a novel IGR: potency and cross-resistance.
2003 Dec
Variation in response to neonicotinoid insecticides in peach-potato aphids, Myzus persicae (Hemiptera: Aphididae).
2003 Feb
Bisalkaloid derivatives of dicarboxylic acids on the basis of lupinine, anabasine, and cytisine as reversible cholinesterase inhibitors.
2003 Jan-Feb
[Sensitive nonradioactive screening method for compounds interacting with alpha7-cholinoreceptor].
2003 Jul-Aug
Fast analysis of nicotine related alkaloids in tobacco and cigarette smoke by megabore capillary gas chromatography.
2003 Oct 31
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
Quantitative structure-activity relationship study using refractotopological state atom index on some neonicotinoid insecticides.
2004 Dec 1
Ligation of CD47 during monocyte differentiation into dendritic cells results in reduced capacity for interleukin-12 production.
2004 Jan
Structural diversity and defensive properties of norditerpenoid alkaloids.
2004 Jul
Inhibitory effect of cadmium and tobacco alkaloids on expansion of porcine oocyte-cumulus complexes.
2004 Mar
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
[Biomarkers of tobacco smoke].
2005
Role of neonicotinyl insecticides in Washington apple integrated pest management. Part II. Nontarget effects on integrated mite control.
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
Alkaloids of Haloxylon salicornicum (Moq.) Bunge ex Boiss. (Chenopodiaceae).
2005 Dec
Feeding responses of free-flying honeybees to secondary compounds mimicking floral nectars.
2005 Dec
Analysis of pesticides in fruits by pressurized liquid extraction and liquid chromatography-ion trap-triple stage mass spectrometry.
2005 Dec 9
Acute and subacute effects of tobacco alkaloids, tobacco-specific nitrosamines and phenethyl isothiocyanate on N'-nitrosonornicotine metabolism in rats.
2005 Nov 15
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
Complete assignments 1H and 13C NMR spectral data of four anabaseine derivatives.
2006 Dec
[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
Relative toxicities and neuromuscular nicotinic receptor agonistic potencies of anabasine enantiomers and anabaseine.
2006 Mar-Apr
A nicotinic acetylcholine receptor mutation (Y151S) causes reduced agonist potency to a range of neonicotinoid insecticides.
2006 Nov
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
Nicotine lozenges for the treatment of smokeless tobacco use.
2007 Feb
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
Effects of tobacco and cigarette smoke extracts on serotonergic raphe neurons in the rat.
2007 Jun 11
Technical comment on Adler et al. (2006): experimental design compromises conclusions.
2007 Mar
A hypothesis to account for the selective and diverse actions of neonicotinoid insecticides at their molecular targets, nicotinic acetylcholine receptors: catch and release in hydrogen bond networks.
2007 Mar
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
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
Role of nicotinic and estrogen signaling during experimental acute and chronic bladder inflammation.
2008 Jan
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
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 Mon Mar 31 19:42:27 GMT 2025
Edited
by admin
on Mon Mar 31 19:42:27 GMT 2025
Record UNII
LMS11II2LO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-87504
Preferred Name English
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
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 Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
EPA PESTICIDE CODE 6001
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
NCI_THESAURUS C221
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
Code System Code Type Description
MESH
D000691
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-791-3
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
CHEBI
28986
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
FDA UNII
LMS11II2LO
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
PUBCHEM
205586
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
ALANWOOD
anabasine
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
RS_ITEM_NUM
1463382
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
WIKIPEDIA
ANABASINE
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
MERCK INDEX
m1882
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY Merck Index
HSDB
3462
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
NCI_THESAURUS
C124073
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
NSC
87504
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
CHEBI
74
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
CAS
494-52-0
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
PRIMARY
EPA CompTox
DTXSID9041607
Created by admin on Mon Mar 31 19:42:27 GMT 2025 , Edited by admin on Mon Mar 31 19:42:27 GMT 2025
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