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
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
| 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 |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
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| 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 |
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| Structural diversity and defensive properties of norditerpenoid alkaloids. | 2004 Jul |
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| The structural basis for GTS-21 selectivity between human and rat nicotinic alpha7 receptors. | 2004 Jul |
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| [Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin]. | 2004 Jul-Aug |
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| Residential treatment for smokeless tobacco use: a case series. | 2004 Jun |
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| 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 |
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| A general procedure for the enantioselective synthesis of the minor tobacco alkaloids nornicotine, anabasine, and anatabine. | 2005 Oct 31 |
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| 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
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
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Thu Jul 06 02:24:20 UTC 2023
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Thu Jul 06 02:24:20 UTC 2023
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| Record UNII |
LMS11II2LO
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C737
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EPA PESTICIDE CODE |
6001
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NCI_THESAURUS |
C221
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D000691
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207-791-3
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28986
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LMS11II2LO
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205586
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anabasine
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1463382
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ANABASINE
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M1882
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3462
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C124073
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87504
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74
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494-52-0
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DTXSID9041607
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| Related Record | Type | Details | ||
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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.
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ANABASINE (ug/cigarette)
Canadian = 67.1 SD(9.4)
Imported = 63.3 SD(6.5)
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |
