Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H14N2.2ClH |
| Molecular Weight | 235.153 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.C1CC[C@H](NC1)C2=CN=CC=C2
InChI
InChIKey=YVAXNODSVITPGV-XRIOVQLTSA-N
InChI=1S/C10H14N2.2ClH/c1-2-7-12-10(5-1)9-4-3-6-11-8-9;;/h3-4,6,8,10,12H,1-2,5,7H2;2*1H/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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|
| 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 |
|
| Separation and measurement of plant alkaloid enantiomers by RP-HPLC analysis of their Fmoc-Alanine analogs. | 2008-04-29 |
|
| Modulation of spontaneous hippocampal synaptic events with 5-hydroxyindole, 4OH-GTS-21, and rAAV-mediated alpha7 nicotinic receptor gene transfer. | 2008-04-08 |
|
| Enantiomeric analysis of anatabine, nornicotine and anabasine in commercial tobacco by multi-dimensional gas chromatography and mass spectrometry. | 2008-04-01 |
|
| The fetal cleft palate: v. elucidation of the mechanism of palatal clefting in the congenital caprine model. | 2008-04 |
|
| Sequential preconcentration by coupling of field amplified sample injection with pseudo isotachophoresis-acid stacking for analysis of alkaloids in capillary electrophoresis. | 2008-03 |
|
| Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine. | 2008-01-09 |
|
| Role of nicotinic and estrogen signaling during experimental acute and chronic bladder inflammation. | 2008-01 |
|
| Effect of anabasine on catecholamine secretion from the perfused rat adrenal medulla. | 2007-12 |
|
| The effect of the cholinergic anti-inflammatory pathway on experimental colitis. | 2007-11 |
|
| Blocking actions of alkylene-tethered bis-neonicotinoids on nicotinic acetylcholine receptors expressed by terminal abdominal ganglion neurons of Periplaneta americana. | 2007-10-02 |
|
| Analyses of tobacco alkaloids by cation-selective exhaustive injection sweeping microemulsion electrokinetic chromatography. | 2007-09-14 |
|
| 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 |
|
| Effects of tobacco and cigarette smoke extracts on serotonergic raphe neurons in the rat. | 2007-06-11 |
|
| Simultaneous determination of neonicotinoid insecticides in agricultural samples by solid-phase extraction cleanup and liquid chromatography equipped with diode-array detection. | 2007-05-16 |
|
| CE with sequential light-emitting diode-induced fluorescence and electro-chemiluminescence detections for the determination of amino acids and alkaloids. | 2007-04 |
|
| Synthesis, insecticidal activity, and QSAR of novel nitromethylene neonicotinoids with tetrahydropyridine fixed cis configuration and exo-ring ether modification. | 2007-03-21 |
|
| Technical comment on Adler et al. (2006): experimental design compromises conclusions. | 2007-03 |
|
| 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 |
|
| Specific detection of anabasine, nicotine, and nicotine metabolites in urine by liquid chromatography-tandem mass spectrometry. | 2006-12 |
|
| Complete assignments 1H and 13C NMR spectral data of four anabaseine derivatives. | 2006-12 |
|
| 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 |
|
| 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
Created
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admin
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Edited
Mon Mar 31 19:41:36 GMT 2025
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on
Mon Mar 31 19:41:36 GMT 2025
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| Record UNII |
I47666V43D
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| Record Status |
Validated (UNII)
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| Record Version |
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31945-06-9
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I47666V43D
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DTXSID20185782
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PARENT -> SALT/SOLVATE |
