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2743-90-0,MFCD00078278
Catalog No.:AA00BCBH

2743-90-0 | (R,S)-Anatabine

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5mg
≥95%
in stock  
$53.00   $37.00
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100mg
95%
in stock  
$61.00   $43.00
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250mg
95%
in stock  
$99.00   $69.00
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1g
97%
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$378.00   $264.00
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5g
97%
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$1,308.00   $916.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00BCBH
Chemical Name:
(R,S)-Anatabine
CAS Number:
2743-90-0
Molecular Formula:
C10H12N2
Molecular Weight:
160.2157
MDL Number:
MFCD00078278
SMILES:
C1=CCC(NC1)c1cccnc1
Properties
Computed Properties
 
Complexity:
165  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
1  
Undefined Atom Stereocenter Count:
1  
XLogP3:
0.9  

Downstream Synthesis Route
122-04-3    2743-90-0   
(<i>R</i>)-1-(4-Nitro-benzoyl)-1,2,3,6-tetrahydro-2,3'bipyridyl 

[1]Spaeth;Kesztler[ChemischeBerichte,1937,vol.70,p.704,707]

122-04-3    2743-90-0   
(<i>S</i>)-1-(4-Nitro-benzoyl)-1,2,3,6-tetrahydro-2,3'bipyridyl 

[1]Spaeth;Kesztler[ChemischeBerichte,1937,vol.70,p.704,707]

122-04-3    2743-90-0   
(+/-)-1-(4-Nitro-benzoyl)-1,2,3,6-tetrahydro-2,3'bipyridyl 

[1]Spaeth;Kesztler[ChemischeBerichte,1937,vol.70,p.704,707]

[1]ArchivesofBiochemistry,1959,vol.80,p.258,263

[1]Spaeth;Kesztler[ChemischeBerichte,1937,vol.70,p.704,707]

Literature

Title: Anatabine ameliorates experimental autoimmune thyroiditis.

Journal: Endocrinology 20120901

Title: Identification of wounding and topping responsive small RNAs in tobacco (Nicotiana tabacum).

Journal: BMC plant biology 20120101

Title: An interspecific Nicotiana hybrid as a useful and cost-effective platform for production of animal vaccines.

Journal: PloS one 20120101

Title: A one-year monitoring of nicotine use in sport: frontier between potential performance enhancement and addiction issues.

Journal: Forensic science international 20111210

Title: Anatabine lowers Alzheimer's Aβ production in vitro and in vivo.

Journal: European journal of pharmacology 20111130

Title: Simultaneous quantification of nicotine and metabolites in rat brain by liquid chromatography-tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20111115

Title: RNAi-mediated down-regulation of ornithine decarboxylase (ODC) leads to reduced nicotine and increased anatabine levels in transgenic Nicotiana tabacum L.

Journal: Phytochemistry 20110401

Title: Vacuole-localized berberine bridge enzyme-like proteins are required for a late step of nicotine biosynthesis in tobacco.

Journal: Plant physiology 20110401

Title: Clustered transcription factor genes regulate nicotine biosynthesis in tobacco.

Journal: The Plant cell 20101001

Title: Identification and quantification of nicotine biomarkers in human oral fluid from individuals receiving low-dose transdermal nicotine: a preliminary study.

Journal: Journal of analytical toxicology 20100901

Title: Natural toxins for use in pest management.

Journal: Toxins 20100801

Title: The pyrolysis of (-)-(S)-nicotine: racemization and decomposition.

Journal: Chirality 20100505

Title: A novel validated procedure for the determination of nicotine, eight nicotine metabolites and two minor tobacco alkaloids in human plasma or urine by solid-phase extraction coupled with liquid chromatography-electrospray ionization-tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100315

Title: A contribution to identification of novel regulators of plant response to sulfur deficiency: characteristics of a tobacco gene UP9C, its protein product and the effects of UP9C silencing.

Journal: Molecular plant 20100301

Title: Parent quit attempts after counseling to reduce children's secondhand smoke exposure and promote cessation: main and moderating relationships.

Journal: Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20091201

Title: Silencing of PMT expression caused a surge of anatabine accumulation in tobacco.

Journal: Molecular biology reports 20091101

Title: The addition of five minor tobacco alkaloids increases nicotine-induced hyperactivity, sensitization and intravenous self-administration in rats.

Journal: The international journal of neuropsychopharmacology 20091101

Title: Validation of a GC-FID method for rapid quantification of nicotine in fermented extracts prepared from Nicotiana tabacum fresh leaves and studies of nicotine metabolites.

Journal: Journal of pharmaceutical and biomedical analysis 20090712

Title: The A622 gene in Nicotiana glauca (tree tobacco): evidence for a functional role in pyridine alkaloid synthesis.

Journal: Plant molecular biology 20090201

Title: Determination of nicotine, cotinine, and related alkaloids in human urine and saliva by automated in-tube solid-phase microextraction coupled with liquid chromatography-mass spectrometry.

Journal: Journal of pharmaceutical and biomedical analysis 20090115

Title: Enantioseparation of nicotine alkaloids in cigarettes by CE using sulfated beta-CD as a chiral selector and a capillary coated with amino groups.

Journal: Electrophoresis 20090101

Title: Nicotine content and delivery across tobacco products.

Journal: Handbook of experimental pharmacology 20090101

Title: Why does anatabine, but not nicotine, accumulate in jasmonate-elicited cultured tobacco BY-2 cells?

Journal: Plant & cell physiology 20080801

Title: [Rapid determination of alkaloids in tobacco using gas chromatography-mass spectrometry with full scan-selected ion monitoring mode].

Journal: Se pu = Chinese journal of chromatography 20080501

Title: Enantiomeric analysis of anatabine, nornicotine and anabasine in commercial tobacco by multi-dimensional gas chromatography and mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080401

Title: Antisense-mediated reduction in ADC activity causes minor alterations in the alkaloid profile of cultured hairy roots and regenerated transgenic plants of Nicotiana tabacum.

Journal: Phytochemistry 20071001

Title: Analyses of tobacco alkaloids by cation-selective exhaustive injection sweeping microemulsion electrokinetic chromatography.

Journal: Journal of chromatography. A 20070914

Title: 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.

Journal: Rapid communications in mass spectrometry : RCM 20070101

Title: Acute and subacute effects of tobacco alkaloids, tobacco-specific nitrosamines and phenethyl isothiocyanate on N'-nitrosonornicotine metabolism in rats.

Journal: Toxicology 20051115

Title: A general procedure for the enantioselective synthesis of the minor tobacco alkaloids nornicotine, anabasine, and anatabine.

Journal: The AAPS journal 20050901

Title: Stereoselectivity of the demethylation of nicotine piperidine homologues by Nicotiana plumbaginifolia cell suspension cultures.

Journal: Phytochemistry 20050801

Title: [What are the markers of tobacco smoking?].

Journal: Journal de gynecologie, obstetrique et biologie de la reproduction 20050401

Title: [Biomarkers of tobacco smoke].

Journal: Przeglad lekarski 20050101

Title: A comparison of urinary biomarkers of tobacco and carcinogen exposure in smokers.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20041001

Title: Anatalline and other methyl jasmonate-inducible nicotine alkaloids from Nicotiana tabacum cv. By-2 cell cultures.

Journal: Planta medica 20041001

Title: Nicotine's defensive function in nature.

Journal: PLoS biology 20040801

Title: Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6.

Journal: Biochemical pharmacology 20040215

Title: Effects of reduced cigarette smoking on the uptake of a tobacco-specific lung carcinogen.

Journal: Journal of the National Cancer Institute 20040121

Title: Fast analysis of nicotine related alkaloids in tobacco and cigarette smoke by megabore capillary gas chromatography.

Journal: Journal of chromatography. A 20031031

Title: Antisense-mediated down-regulation of putrescine N-methyltransferase activity in transgenic Nicotiana tabacum L. can lead to elevated levels of anatabine at the expense of nicotine.

Journal: Plant molecular biology 20030901

Title: Anabasine and anatabine as biomarkers for tobacco use during nicotine replacement therapy.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20021201

Title: Determination of nicotine and other minor alkaloids in international cigarettes by solid-phase microextraction and gas chromatography/mass spectrometry.

Journal: Analytical chemistry 20021001

Title: Determination of tobacco alkaloids by gas chromatography with nitrogen-phosphorus detection.

Journal: Analytical and bioanalytical chemistry 20020401

Title: Comparison of methods for extraction of tobacco alkaloids.

Journal: Journal of AOAC International 20010101

Title: Lai FY, et al. Levels of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in raw wastewater as an innovative perspective for investigating population-wide exposure to third-hand smoke. Sci Rep. 2018 Sep 5;8(1):13254.

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