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
| 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 |
| 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 |
|---|---|---|
| Fatal poisoning from Nicotiana glauca leaves: identification of anabasine by gas-chromatography/mass spectrometry. | 2000 May |
|
| Benzylidene analogs of anabaseine display partial agonist and antagonist properties at the mouse 5-hydroxytryptamine(3A) receptor. | 2001 Dec |
|
| The discovery of thiamethoxam: a second-generation neonicotinoid. | 2001 Feb |
|
| Comparison of methods for extraction of tobacco alkaloids. | 2001 Mar-Apr |
|
| Determination of tobacco alkaloids in single plant cells by capillary electrophoresis. | 2001 May 11 |
|
| Determination of tobacco alkaloids by gas chromatography with nitrogen-phosphorus detection. | 2002 Apr |
|
| 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 |
|
| Structure-activity relationships of benzylidene anabaseines in nicotinic acetylcholine receptors of cockroach nerve cords. | 2002 Sep |
|
| Variation in response to neonicotinoid insecticides in peach-potato aphids, Myzus persicae (Hemiptera: Aphididae). | 2003 Feb |
|
| Bisalkaloid derivatives of dicarboxylic acids on the basis of lupinine, anabasine, and cytisine as reversible cholinesterase inhibitors. | 2003 Jan-Feb |
|
| Inhibition of barnacle larval settlement and crustacean toxicity of some hoplonemertine pyridyl alkaloids. | 2003 Jul |
|
| [Sensitive nonradioactive screening method for compounds interacting with alpha7-cholinoreceptor]. | 2003 Jul-Aug |
|
| 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 |
|
| 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 |
|
| Ligation of CD47 during monocyte differentiation into dendritic cells results in reduced capacity for interleukin-12 production. | 2004 Jan |
|
| Structural diversity and defensive properties of norditerpenoid alkaloids. | 2004 Jul |
|
| [Biomarkers of tobacco smoke]. | 2005 |
|
| Alkaloids of Haloxylon salicornicum (Moq.) Bunge ex Boiss. (Chenopodiaceae). | 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 |
|
| Specific detection of anabasine, nicotine, and nicotine metabolites in urine by liquid chromatography-tandem mass spectrometry. | 2006 Dec |
|
| Substrate specificity of rabbit aldehyde oxidase for nitroguanidine and nitromethylene neonicotinoid insecticides. | 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 |
|
| N-terminal domains in mouse and human 5-hydroxytryptamine3A receptors confer partial agonist and antagonist properties to benzylidene analogs of anabaseine. | 2006 Jun |
|
| Women's health among the Chumash. | 2006 Mar |
|
| Relative toxicities and neuromuscular nicotinic receptor agonistic potencies of anabasine enantiomers and anabaseine. | 2006 Mar-Apr |
|
| The effect of the cholinergic anti-inflammatory pathway on experimental colitis. | 2007 Nov |
|
| Analyses of tobacco alkaloids by cation-selective exhaustive injection sweeping microemulsion electrokinetic chromatography. | 2007 Sep 14 |
|
| Enantiomeric analysis of anatabine, nornicotine and anabasine in commercial tobacco by multi-dimensional gas chromatography and mass spectrometry. | 2008 Apr 1 |
|
| Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine. | 2008 Jan 9 |
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
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on
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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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DTXSID20185782
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PARENT -> SALT/SOLVATE |
