(S)-Anabasine hydrochloride
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MedKoo CAT#: 575805

CAS#: 53912-89-3 (S-isomer HCl)

Description: Anabasine HCl is used as an insecticide and as a clinical biomarker for tobacco smoke exposure. It is also a depolarizing NMJ blocker, nAChr antagonist, aromatase inhibitor, and teratogen found in species of Nicotiana.

Chemical Structure

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(S)-Anabasine hydrochloride
CAS# 53912-89-3 (S-isomer HCl)
Instruction

Theoretical Analysis

MedKoo Cat#: 575805
Name: (S)-Anabasine hydrochloride
CAS#: 53912-89-3 (S-isomer HCl)
Chemical Formula: C10H15ClN2
Exact Mass: 198.09
Molecular Weight: 198.690
Elemental Analysis: C, 60.45; H, 7.61; Cl, 17.84; N, 14.10

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50mg USD 450 2 Weeks
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Related CAS #: 494-52-0 (S-isomer free base)   15251-47-5 (HCl)   53912-89-3 (S-isomer HCl)   13078-04-1 (free base)  

Synonym: Anabasine hydrochloride; Anabasin chloride; Anabasine monohydrochloride; Anabasine HCl; Gamibasin; (S)-Anabasine hydrochloride; (+)-Anabasine hydrochloride

IUPAC/Chemical Name: Pyridine, 3-(2-piperidinyl)-, monohydrochloride, (S)-

InChi Key: VTMZQNZVYCJLGG-PPHPATTJSA-N

InChi Code: InChI=1S/C10H14N2.ClH/c1-2-7-12-10(5-1)9-4-3-6-11-8-9;/h3-4,6,8,10,12H,1-2,5,7H2;1H/t10-;/m0./s1

SMILES Code: Cl.C1CC[C@H](NC1)c2cccnc2

Appearance:

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 198.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Bade R, White JM, Tscharke BJ, Ghetia M, Abdelaziz A, Gerber C. Anabasine- based measurement of cigarette consumption using wastewater analysis. Drug Test Anal. 2020 Sep;12(9):1393-1398. doi: 10.1002/dta.2874. Epub 2020 Jun 26. PMID: 32506745.


2: Bendik PB, Rutt SM, Pine BN, Sosnoff CS, Blount BC, Zhu W, Feng J, Wang L. Anabasine and Anatabine Exposure Attributable to Cigarette Smoking: National Health and Nutrition Examination Survey (NHANES) 2013-2014. Int J Environ Res Public Health. 2022 Aug 8;19(15):9744. doi: 10.3390/ijerph19159744. PMID: 35955098; PMCID: PMC9368097.


3: Muldakhmetov Z, Fazylov S, Nurkenov O, Gazaliev A, Sarsenbekova A, Pustolaikina I, Nurmaganbetov Z, Seilkhanov O, Alsfouk AA, Elkaeed EB, Eissa IH, Metwaly AM. Combined Computational and Experimental Studies of Anabasine Encapsulation by Beta-Cyclodextrin. Plants (Basel). 2022 Aug 31;11(17):2283. doi: 10.3390/plants11172283. PMID: 36079665; PMCID: PMC9460387.


4: Zheng Q, Gerber C, Steadman KJ, Lin CY, Tscharke BJ, O'Brien JW, Hobson P, Toms LM, Mueller JF, Thomas KV, Thai PK. Improving Wastewater-Based Tobacco Use Estimates Using Anabasine. Environ Sci Technol. 2023 May 30;57(21):7958-7965. doi: 10.1021/acs.est.3c01510. Epub 2023 May 16. PMID: 37192131.


5: Hoffman AC, Evans SE. Abuse potential of non-nicotine tobacco smoke components: acetaldehyde, nornicotine, cotinine, and anabasine. Nicotine Tob Res. 2013 Mar;15(3):622-32. doi: 10.1093/ntr/nts192. Epub 2012 Sep 18. PMID: 22990226.


6: Palmer-Young EC, Hogeboom A, Kaye AJ, Donnelly D, Andicoechea J, Connon SJ, Weston I, Skyrm K, Irwin RE, Adler LS. Context-dependent medicinal effects of anabasine and infection-dependent toxicity in bumble bees. PLoS One. 2017 Aug 23;12(8):e0183729. doi: 10.1371/journal.pone.0183729. PMID: 28832668; PMCID: PMC5568382.


7: Gao Y, Yang X, Wang Z, Zhong Z, Hu Y, Wang Y. Supramolecular Nano- Encapsulation of Anabasine Reduced Its Developmental Toxicity in Zebrafish. Front Chem. 2020 Feb 28;8:134. doi: 10.3389/fchem.2020.00134. PMID: 32185162; PMCID: PMC7058803.


8: Grebenstein PE, Erickson P, Grace M, Kotz CM. Anatabine, Nornicotine, and Anabasine Reduce Weight Gain and Body Fat through Decreases in Food Intake and Increases in Physical Activity. J Clin Med. 2022 Jan 18;11(3):481. doi: 10.3390/jcm11030481. PMID: 35159932; PMCID: PMC8837150.


9: Feldhammer M, Ritchie JC. Anabasine Is a Poor Marker for Determining Smoking Status of Transplant Patients. Clin Chem. 2017 Feb;63(2):604-606. doi: 10.1373/clinchem.2016.265546. Epub 2016 Dec 16. PMID: 27986784.


10: Mukusheva GK, Zhasymbekova AR, Zhumagalieva ZZ, Seidakhmetova RB, Nurkenov OA, Akishina EA, Petkevich SK, Dikusar EA, Potkin VI. Synthesis and Biological Activity of N-acyl Anabasine and Cytisine Derivatives with Adamantane, Pyridine and 1,2-Azole Fragments. Molecules. 2022 Oct 31;27(21):7387. doi: 10.3390/molecules27217387. PMID: 36364219; PMCID: PMC9656753.


11: Welch KD, Lee ST, Panter KE, Gardner DR, Knoppel EL, Green BT, Hammond CK, Hammond ZJ, Pfister JA. Studies on the teratogenicity of anabasine in a rat model. Toxicon. 2014 Sep;87:32-7. doi: 10.1016/j.toxicon.2014.05.018. Epub 2014 Jun 4. PMID: 24905648.


12: Zheng Q, Eaglesham G, Tscharke BJ, O'Brien JW, Li J, Thompson J, Shimko KM, Reeks T, Gerber C, Thomas KV, Thai PK. Determination of anabasine, anatabine, and nicotine biomarkers in wastewater by enhanced direct injection LC-MS/MS and evaluation of their in-sewer stability. Sci Total Environ. 2020 Nov 15;743:140551. doi: 10.1016/j.scitotenv.2020.140551. Epub 2020 Jun 26. PMID: 32653706.


13: Thorburn LP, Adler LS, Irwin RE, Palmer-Young EC. Variable effects of nicotine, anabasine, and their interactions on parasitized bumble bees. F1000Res. 2015 Sep 21;4:880. doi: 10.12688/f1000research.6870.2. PMID: 26998225; PMCID: PMC4786900.


14: Jacob P 3rd, Hatsukami D, Severson H, Hall S, Yu L, Benowitz NL. Anabasine and anatabine as biomarkers for tobacco use during nicotine replacement therapy. Cancer Epidemiol Biomarkers Prev. 2002 Dec;11(12):1668-73. PMID: 12496059.


15: Murphy NG, Albin C, Tai W, Benowitz NL. Anabasine toxicity from a topical folk remedy. Clin Pediatr (Phila). 2006 Sep;45(7):669-71. doi: 10.1177/0009922806291022. PMID: 16928847.


16: Lee ST, Wildeboer K, Panter KE, Kem WR, Gardner DR, Molyneux RJ, Chang CW, Soti F, Pfister JA. Relative toxicities and neuromuscular nicotinic receptor agonistic potencies of anabasine enantiomers and anabaseine. Neurotoxicol Teratol. 2006 Mar-Apr;28(2):220-8. doi: 10.1016/j.ntt.2005.12.010. Epub 2006 Feb 20. PMID: 16488116.


17: Xu T, Guo Y, Lu J, Shan J, Lin L, Qian W, Chen W, Wang J, Lv X, Ke M, Kong D, Shen Q, Zhu Y, Liu P, Su J, Lu W, Li Y, Gao P, Liu S. Untargeted serum metabolomics and potential biomarkers for Sjögren's syndrome. Clin Exp Rheumatol. 2021 Nov-Dec;39 Suppl 133(6):23-29. doi: 10.55563/clinexprheumatol/ylte6v. Epub 2021 Jun 29. PMID: 34251320.


18: von Weymarn LB, Thomson NM, Donny EC, Hatsukami DK, Murphy SE. Quantitation of the Minor Tobacco Alkaloids Nornicotine, Anatabine, and Anabasine in Smokers' Urine by High Throughput Liquid Chromatography-Mass Spectrometry. Chem Res Toxicol. 2016 Mar 21;29(3):390-7. doi: 10.1021/acs.chemrestox.5b00521. Epub 2016 Feb 12. PMID: 26825008; PMCID: PMC5155587.


19: Suh-Lailam BB, Haglock-Adler CJ, Carlisle HJ, Ohman T, McMillin GA. Reference interval determination for anabasine: a biomarker of active tobacco use. J Anal Toxicol. 2014 Sep;38(7):416-20. doi: 10.1093/jat/bku059. Epub 2014 Jun 17. PMID: 24939383.


20: Levin ED, Hao I, Burke DA, Cauley M, Hall BJ, Rezvani AH. Effects of tobacco smoke constituents, anabasine and anatabine, on memory and attention in female rats. J Psychopharmacol. 2014 Oct;28(10):915-22. doi: 10.1177/0269881114543721. Epub 2014 Aug 13. PMID: 25122040; PMCID: PMC4305443.

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