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 |
|---|---|---|
| Benzylidene analogs of anabaseine display partial agonist and antagonist properties at the mouse 5-hydroxytryptamine(3A) receptor. | 2001 Dec |
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| Insecticidal and neural activities of candidate photoaffinity probes for neonicotinoid binding sites. | 2001 Jul |
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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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| Quantitative structure-activity relationship study on some azidopyridinyl neonicotinoid insecticides for their selective affinity towards the drosophila nicotinic receptor over mammalian alpha4beta2 receptor using electrotopological state atom index. | 2003 |
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| Novaluron (Rimon), a novel IGR: potency and cross-resistance. | 2003 Dec |
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| Variation in response to neonicotinoid insecticides in peach-potato aphids, Myzus persicae (Hemiptera: Aphididae). | 2003 Feb |
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| Bisalkaloid derivatives of dicarboxylic acids on the basis of lupinine, anabasine, and cytisine as reversible cholinesterase inhibitors. | 2003 Jan-Feb |
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| [Sensitive nonradioactive screening method for compounds interacting with alpha7-cholinoreceptor]. | 2003 Jul-Aug |
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| Fast analysis of nicotine related alkaloids in tobacco and cigarette smoke by megabore capillary gas chromatography. | 2003 Oct 31 |
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| Nicotine's defensive function in nature. | 2004 Aug |
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| Anabasine, a selective nicotinic acetylcholine receptor agonist, antagonizes MK-801-elicited mouse popping behavior, an animal model of schizophrenia. | 2004 Aug 31 |
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| Quantitative structure-activity relationship study using refractotopological state atom index on some neonicotinoid insecticides. | 2004 Dec 1 |
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| Ligation of CD47 during monocyte differentiation into dendritic cells results in reduced capacity for interleukin-12 production. | 2004 Jan |
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| Structural diversity and defensive properties of norditerpenoid alkaloids. | 2004 Jul |
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| Inhibitory effect of cadmium and tobacco alkaloids on expansion of porcine oocyte-cumulus complexes. | 2004 Mar |
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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 |
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| [Biomarkers of tobacco smoke]. | 2005 |
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| Role of neonicotinyl insecticides in Washington apple integrated pest management. Part II. Nontarget effects on integrated mite control. | 2005 |
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| [What are the markers of tobacco smoking?]. | 2005 Apr |
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| Stereoselectivity of the demethylation of nicotine piperidine homologues by Nicotiana plumbaginifolia cell suspension cultures. | 2005 Aug |
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| Neonicotinoids show selective and diverse actions on their nicotinic receptor targets: electrophysiology, molecular biology, and receptor modeling studies. | 2005 Aug |
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| Alkaloids of Haloxylon salicornicum (Moq.) Bunge ex Boiss. (Chenopodiaceae). | 2005 Dec |
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| Feeding responses of free-flying honeybees to secondary compounds mimicking floral nectars. | 2005 Dec |
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| Analysis of pesticides in fruits by pressurized liquid extraction and liquid chromatography-ion trap-triple stage mass spectrometry. | 2005 Dec 9 |
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| Acute and subacute effects of tobacco alkaloids, tobacco-specific nitrosamines and phenethyl isothiocyanate on N'-nitrosonornicotine metabolism in rats. | 2005 Nov 15 |
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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 |
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| Cytisine for smoking cessation: a literature review and a meta-analysis. | 2006 Aug 14-28 |
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| Complete assignments 1H and 13C NMR spectral data of four anabaseine derivatives. | 2006 Dec |
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| [Analogs of anabasine as reversible and irreversible inhibitors of choline esterases of different animals]. | 2006 Jan-Feb |
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| Chloropyridinyl neonicotinoid insecticides: diverse molecular substituents contribute to facile metabolism in mice. | 2006 Jul |
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| Relative toxicities and neuromuscular nicotinic receptor agonistic potencies of anabasine enantiomers and anabaseine. | 2006 Mar-Apr |
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| A nicotinic acetylcholine receptor mutation (Y151S) causes reduced agonist potency to a range of neonicotinoid insecticides. | 2006 Nov |
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| 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 |
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| Nicotine lozenges for the treatment of smokeless tobacco use. | 2007 Feb |
|
| 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 |
|
| Effects of tobacco and cigarette smoke extracts on serotonergic raphe neurons in the rat. | 2007 Jun 11 |
|
| Technical comment on Adler et al. (2006): experimental design compromises conclusions. | 2007 Mar |
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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 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 |
|
| 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 |
|
| 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 |
|
| Role of nicotinic and estrogen signaling during experimental acute and chronic bladder inflammation. | 2008 Jan |
|
| 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.
| Substance Class |
Chemical
Created
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Mon Mar 31 19:42:27 GMT 2025
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| Record UNII |
LMS11II2LO
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| Record Status |
Validated (UNII)
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| Classification Tree | Code System | Code | ||
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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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PRIMARY | Merck Index | ||
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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 |
