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=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
| 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 |
|---|---|---|
| Screening of tobacco smoke condensate for nicotinic acetylcholine receptor ligands using cellular membrane affinity chromatography columns and missing peak chromatography. | 2008-09-29 |
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| 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. | 2008-05-02 |
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| Separation and measurement of plant alkaloid enantiomers by RP-HPLC analysis of their Fmoc-Alanine analogs. | 2008-04-29 |
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| Modulation of spontaneous hippocampal synaptic events with 5-hydroxyindole, 4OH-GTS-21, and rAAV-mediated alpha7 nicotinic receptor gene transfer. | 2008-04-08 |
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| Enantiomeric analysis of anatabine, nornicotine and anabasine in commercial tobacco by multi-dimensional gas chromatography and mass spectrometry. | 2008-04-01 |
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| The fetal cleft palate: v. elucidation of the mechanism of palatal clefting in the congenital caprine model. | 2008-04 |
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| Sequential preconcentration by coupling of field amplified sample injection with pseudo isotachophoresis-acid stacking for analysis of alkaloids in capillary electrophoresis. | 2008-03 |
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| Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine. | 2008-01-09 |
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| Role of nicotinic and estrogen signaling during experimental acute and chronic bladder inflammation. | 2008-01 |
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| Effect of anabasine on catecholamine secretion from the perfused rat adrenal medulla. | 2007-12 |
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| The effect of the cholinergic anti-inflammatory pathway on experimental colitis. | 2007-11 |
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| Blocking actions of alkylene-tethered bis-neonicotinoids on nicotinic acetylcholine receptors expressed by terminal abdominal ganglion neurons of Periplaneta americana. | 2007-10-02 |
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| Analyses of tobacco alkaloids by cation-selective exhaustive injection sweeping microemulsion electrokinetic chromatography. | 2007-09-14 |
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| The alpha7 nicotinic receptor agonist 4OH-GTS-21 protects axotomized septohippocampal cholinergic neurons in wild type but not amyloid-overexpressing transgenic mice. | 2007-08-10 |
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| Effects of tobacco and cigarette smoke extracts on serotonergic raphe neurons in the rat. | 2007-06-11 |
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| Simultaneous determination of neonicotinoid insecticides in agricultural samples by solid-phase extraction cleanup and liquid chromatography equipped with diode-array detection. | 2007-05-16 |
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| CE with sequential light-emitting diode-induced fluorescence and electro-chemiluminescence detections for the determination of amino acids and alkaloids. | 2007-04 |
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| Synthesis, insecticidal activity, and QSAR of novel nitromethylene neonicotinoids with tetrahydropyridine fixed cis configuration and exo-ring ether modification. | 2007-03-21 |
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| Technical comment on Adler et al. (2006): experimental design compromises conclusions. | 2007-03 |
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| 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. | 2007-03 |
|
| Reversal of agonist selectivity by mutations of conserved amino acids in the binding site of nicotinic acetylcholine receptors. | 2007-02-23 |
|
| 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. | 2007-02-07 |
|
| Nicotine lozenges for the treatment of smokeless tobacco use. | 2007-02 |
|
| 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 |
|
| Influence of agonists and antagonists on the segmental motion of residues near the agonist binding pocket of the acetylcholine-binding protein. | 2006-12-22 |
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| Specific detection of anabasine, nicotine, and nicotine metabolites in urine by liquid chromatography-tandem mass spectrometry. | 2006-12 |
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| Complete assignments 1H and 13C NMR spectral data of four anabaseine derivatives. | 2006-12 |
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| A nicotinic acetylcholine receptor mutation (Y151S) causes reduced agonist potency to a range of neonicotinoid insecticides. | 2006-11 |
|
| Role in the selectivity of neonicotinoids of insect-specific basic residues in loop D of the nicotinic acetylcholine receptor agonist binding site. | 2006-10 |
|
| Anabasine toxicity from a topical folk remedy. | 2006-09 |
|
| Cytisine for smoking cessation: a literature review and a meta-analysis. | 2006-08-16 |
|
| Spectroscopic analysis of benzylidene anabaseine complexes with acetylcholine binding proteins as models for ligand-nicotinic receptor interactions. | 2006-07-25 |
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| Chloropyridinyl neonicotinoid insecticides: diverse molecular substituents contribute to facile metabolism in mice. | 2006-07 |
|
| N-terminal domains in mouse and human 5-hydroxytryptamine3A receptors confer partial agonist and antagonist properties to benzylidene analogs of anabaseine. | 2006-06 |
|
| [Analogs of anabasine as reversible and irreversible inhibitors of choline esterases of different animals]. | 2006-04-04 |
|
| Women's health among the Chumash. | 2006-03 |
|
| Substrate specificity of rabbit aldehyde oxidase for nitroguanidine and nitromethylene neonicotinoid insecticides. | 2006-01 |
|
| Assignment of absolute configuration of cyclic secondary amines by NMR techniques using Mosher's method: a general procedure exemplified with (-)-isoanabasine. | 2006-01 |
|
| Resistance and cross-resistance to neonicotinoid insecticides and spinosad in the Colorado potato beetle, Leptinotarsa decemlineata (Say) (Coleoptera: Chrysomelidae). | 2006-01 |
|
| Analysis of pesticides in fruits by pressurized liquid extraction and liquid chromatography-ion trap-triple stage mass spectrometry. | 2005-12-09 |
|
| Alkaloids of Haloxylon salicornicum (Moq.) Bunge ex Boiss. (Chenopodiaceae). | 2005-12 |
|
| Feeding responses of free-flying honeybees to secondary compounds mimicking floral nectars. | 2005-12 |
|
| Rhesus monkey alpha7 nicotinic acetylcholine receptors: comparisons to human alpha7 receptors expressed in Xenopus oocytes. | 2005-11-07 |
|
| A general procedure for the enantioselective synthesis of the minor tobacco alkaloids nornicotine, anabasine, and anatabine. | 2005-10-31 |
|
| Inhibition of cholinesterases of various origin by anabasine derivatives. | 2005-10-19 |
|
| Cigarette smoking and effects on hormone function in premenopausal women. | 2005-10 |
|
| Smoking and reproduction: the oviduct as a target of cigarette smoke. | 2005-09-28 |
|
| Relative toxicities and neuromuscular nicotinic receptor agonistic potencies of anabasine enantiomers and anabaseine. | 2005-06-16 |
|
| [Biomarkers of tobacco smoke]. | 2005 |
|
| Role of neonicotinyl insecticides in Washington apple integrated pest management. Part II. Nontarget effects on integrated mite control. | 2005 |
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
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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 |
