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.[H][C@]1(CCCCN1)C2=CC=CN=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
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Benzylidene analogs of anabaseine display partial agonist and antagonist properties at the mouse 5-hydroxytryptamine(3A) receptor. | 2001 Dec |
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| Anabasine and anatabine as biomarkers for tobacco use during nicotine replacement therapy. | 2002 Dec |
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| Translocation and translaminar bioavailability of two neonicotinoid insecticides after foliar application to cabbage and cotton. | 2002 Jan |
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| The fetal cleft palate: III. Ultrastructural and functional analysis of palatal development following in utero repair of the congenital model. | 2002 Jun |
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| Enantioselective synthesis of 2-arylpiperidines from chiral lactams. A concise synthesis of (-)-anabasine. | 2002 Mar 7 |
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| Determination of nicotine and other minor alkaloids in international cigarettes by solid-phase microextraction and gas chromatography/mass spectrometry. | 2002 Oct 1 |
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| Structure-activity relationships of benzylidene anabaseines in nicotinic acetylcholine receptors of cockroach nerve cords. | 2002 Sep |
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| [Pharmaceutical botanical studies on some Glycyrrhiza species]. | 2003 Aug |
|
| Novaluron (Rimon), a novel IGR: potency and cross-resistance. | 2003 Dec |
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| Studies on intramolecular Diels-Alder reactions of furo[3,4-c]pyridines in the synthesis of conformationally restricted analogues of nicotine and anabasine. | 2003 May 30 |
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| Dihydropiperazine neonicotinoid compounds. Synthesis and insecticidal activity. | 2003 May 7 |
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| GABAergic systems modulate nicotinic receptor-mediated seizures in mice. | 2003 Sep |
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| 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 |
|
| The structural basis for GTS-21 selectivity between human and rat nicotinic alpha7 receptors. | 2004 Jul |
|
| Residential treatment for smokeless tobacco use: a case series. | 2004 Jun |
|
| 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 |
|
| [What are the markers of tobacco smoking?]. | 2005 Apr |
|
| 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 |
|
| Identification of aldehyde oxidase as the neonicotinoid nitroreductase. | 2005 Feb |
|
| Cigarette smoking and effects on hormone function in premenopausal women. | 2005 Oct |
|
| A general procedure for the enantioselective synthesis of the minor tobacco alkaloids nornicotine, anabasine, and anatabine. | 2005 Oct 31 |
|
| 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 |
|
| 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 |
|
| Women's health among the Chumash. | 2006 Mar |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Technical comment on Adler et al. (2006): experimental design compromises conclusions. | 2007 Mar |
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| Synthesis, insecticidal activity, and QSAR of novel nitromethylene neonicotinoids with tetrahydropyridine fixed cis configuration and exo-ring ether modification. | 2007 Mar 21 |
|
| Blocking actions of alkylene-tethered bis-neonicotinoids on nicotinic acetylcholine receptors expressed by terminal abdominal ganglion neurons of Periplaneta americana. | 2007 Oct 2 |
|
| The fetal cleft palate: v. elucidation of the mechanism of palatal clefting in the congenital caprine model. | 2008 Apr |
|
| 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 |
|
| 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
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.
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45782737
Created by
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31945-06-9
Created by
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I47666V43D
Created by
admin on Fri Dec 15 19:16:18 GMT 2023 , Edited by admin on Fri Dec 15 19:16:18 GMT 2023
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DTXSID20185782
Created by
admin on Fri Dec 15 19:16:18 GMT 2023 , Edited by admin on Fri Dec 15 19:16:18 GMT 2023
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PRIMARY |
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
