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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
The discovery of thiamethoxam: a second-generation neonicotinoid.
2001 Feb
Absolute configuration of anabasine from Messor and Aphaenogaster ants.
2001 May
Determination of tobacco alkaloids by gas chromatography with nitrogen-phosphorus detection.
2002 Apr
Translocation and translaminar bioavailability of two neonicotinoid insecticides after foliar application to cabbage and cotton.
2002 Jan
Accidental fatal poisoning by Nicotiana glauca: identification of anabasine by high performance liquid chromatography/photodiode array/mass spectrometry.
2002 Jul 17
The fetal cleft palate: III. Ultrastructural and functional analysis of palatal development following in utero repair of the congenital model.
2002 Jun
Enantioselective synthesis of 2-arylpiperidines from chiral lactams. A concise synthesis of (-)-anabasine.
2002 Mar 7
Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles.
2002 Sep
Comparative pharmacology of rat and human alpha7 nAChR conducted with net charge analysis.
2002 Sep
Structure-activity relationships of benzylidene anabaseines in nicotinic acetylcholine receptors of cockroach nerve cords.
2002 Sep
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
Variation in response to neonicotinoid insecticides in peach-potato aphids, Myzus persicae (Hemiptera: Aphididae).
2003 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
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
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
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
Analysis of pesticides in fruits by pressurized liquid extraction and liquid chromatography-ion trap-triple stage mass spectrometry.
2005 Dec 9
Identification of aldehyde oxidase as the neonicotinoid nitroreductase.
2005 Feb
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
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
CE with sequential light-emitting diode-induced fluorescence and electro-chemiluminescence detections for the determination of amino acids and alkaloids.
2007 Apr
The alpha7 nicotinic receptor agonist 4OH-GTS-21 protects axotomized septohippocampal cholinergic neurons in wild type but not amyloid-overexpressing transgenic mice.
2007 Aug 10
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
Synthesis, insecticidal activity, and QSAR of novel nitromethylene neonicotinoids with tetrahydropyridine fixed cis configuration and exo-ring ether modification.
2007 Mar 21
Simultaneous determination of neonicotinoid insecticides in agricultural samples by solid-phase extraction cleanup and liquid chromatography equipped with diode-array detection.
2007 May 16
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
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 Fri Dec 15 19:17:01 GMT 2023
Edited
by admin
on Fri Dec 15 19:17:01 GMT 2023
Record UNII
LMS11II2LO
Record Status Validated (UNII)
Record Version
  • Download
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 Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
EPA PESTICIDE CODE 6001
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
NCI_THESAURUS C221
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
Code System Code Type Description
MESH
D000691
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-791-3
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
CHEBI
28986
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
FDA UNII
LMS11II2LO
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
PUBCHEM
205586
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
ALANWOOD
anabasine
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
RS_ITEM_NUM
1463382
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
WIKIPEDIA
ANABASINE
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
MERCK INDEX
m1882
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY Merck Index
HSDB
3462
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
NCI_THESAURUS
C124073
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
NSC
87504
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
CHEBI
74
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
CAS
494-52-0
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID9041607
Created by admin on Fri Dec 15 19:17:01 GMT 2023 , Edited by admin on Fri Dec 15 19:17:01 GMT 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