MedKoo Cat#: 584650 | Name: (S)-Anabasine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Anabasine is a piperidine botanical insecticide.

Chemical Structure

(S)-Anabasine
(S)-Anabasine
CAS#494-52-0 (S-isomer free base)

Theoretical Analysis

MedKoo Cat#: 584650

Name: (S)-Anabasine

CAS#: 494-52-0 (S-isomer free base)

Chemical Formula: C10H14N2

Exact Mass: 162.1157

Molecular Weight: 162.24

Elemental Analysis: C, 74.03; H, 8.70; N, 17.27

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
250mg USD 850.00 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
(S)-Anabasine;(+)-Anabasine; Anabazin
IUPAC/Chemical Name
3-[(2S)-piperidin-2-yl]pyridine
InChi Key
MTXSIJUGVMTTMU-JTQLQIEISA-N
InChi Code
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
SMILES Code
C1([C@H]2NCCCC2)=CC=CN=C1
Appearance
Liquid
Purity
>95% (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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 162.24 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
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PubMed PMID: 26825008; PubMed Central PMCID: PMC5155587. 4: Zheng F, Du X, Chou TH, Robertson AP, Yu EW, VanVeller B, Martin RJ. (S)-5-ethynyl-anabasine, a novel compound, is a more potent agonist than other nicotine alkaloids on the nematode Asu-ACR-16 receptor. Int J Parasitol Drugs Drug Resist. 2017 Apr;7(1):12-22. doi: 10.1016/j.ijpddr.2016.12.001. Epub 2016 Dec 9. PubMed PMID: 28033523; PubMed Central PMCID: PMC5196235. 5: Desai RI, Doyle MR, Withey SL, Bergman J. Nicotinic effects of tobacco smoke constituents in nonhuman primates. Psychopharmacology (Berl). 2016 May;233(10):1779-89. doi: 10.1007/s00213-016-4238-5. Epub 2016 Feb 19. PubMed PMID: 26892379. 6: 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. PubMed PMID: 25122040; PubMed Central PMCID: PMC4305443. 7: Etter JF, Bugey A. E-cigarette liquids: Constancy of content across batches and accuracy of labeling. Addict Behav. 2017 Oct;73:137-143. doi: 10.1016/j.addbeh.2017.05.012. Epub 2017 May 10. PubMed PMID: 28511098. 8: Tscharke BJ, White JM, Gerber JP. Estimates of tobacco use by wastewater analysis of anabasine and anatabine. Drug Test Anal. 2016 Jul;8(7):702-7. doi: 10.1002/dta.1842. Epub 2015 Jul 22. PubMed PMID: 26198173. 9: Wessler I, Gärtner HA, Michel-Schmidt R, Brochhausen C, Schmitz L, Anspach L, Grünewald B, Kirkpatrick CJ. Honeybees Produce Millimolar Concentrations of Non-Neuronal Acetylcholine for Breeding: Possible Adverse Effects of Neonicotinoids. PLoS One. 2016 Jun 10;11(6):e0156886. doi: 10.1371/journal.pone.0156886. eCollection 2016. PubMed PMID: 27285384; PubMed Central PMCID: PMC4902251. 10: Anthony WE, Palmer-Young EC, Leonard AS, Irwin RE, Adler LS. Testing Dose-Dependent Effects of the Nectar Alkaloid Anabasine on Trypanosome Parasite Loads in Adult Bumble Bees. PLoS One. 2015 Nov 6;10(11):e0142496. doi: 10.1371/journal.pone.0142496. eCollection 2015. PubMed PMID: 26545106; PubMed Central PMCID: PMC4636389. 11: Green BT, Lee ST, Welch KD, Cook D, Kem WR. Activation and Desensitization of Peripheral Muscle and Neuronal Nicotinic Acetylcholine Receptors by Selected, Naturally-Occurring Pyridine Alkaloids. Toxins (Basel). 2016 Jul 4;8(7). pii: E204. doi: 10.3390/toxins8070204. PubMed PMID: 27384586; PubMed Central PMCID: PMC4963837. 12: 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. PubMed PMID: 24905648. 13: Zhang H, Breeze T, Bailey A, Garthwaite D, Harrington R, Potts SG. Arthropod Pest Control for UK Oilseed Rape - Comparing Insecticide Efficacies, Side Effects and Alternatives. PLoS One. 2017 Jan 11;12(1):e0169475. doi: 10.1371/journal.pone.0169475. eCollection 2017. PubMed PMID: 28076392; PubMed Central PMCID: PMC5226783. 14: Abdel-Ghany MF, Hussein LA, El Azab NF, El-Khatib AH, Linscheid MW. Simultaneous determination of eight neonicotinoid insecticide residues and two primary metabolites in cucumbers and soil by liquid chromatography-tandem mass spectrometry coupled with QuEChERS. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Sep 15;1031:15-28. doi: 10.1016/j.jchromb.2016.06.020. Epub 2016 Jun 16. PubMed PMID: 27447929. 15: Welch KD, Panter KE, Lee ST, Gardner DR. The effect of intermittent dosing of Nicotiana glauca on teratogenesis in goats. Toxicon. 2015 Jan;93:119-24. doi: 10.1016/j.toxicon.2014.11.232. Epub 2014 Nov 21. PubMed PMID: 25451537. 16: Caine SB, Collins GT, Thomsen M, Wright C, Lanier RK, Mello NK. Nicotine-like behavioral effects of the minor tobacco alkaloids nornicotine, anabasine, and anatabine in male rodents. Exp Clin Psychopharmacol. 2014 Feb;22(1):9-22. doi: 10.1037/a0035749. PubMed PMID: 24490708. 17: DeBoer KD, Dalton HL, Edward FJ, Ryan SM, Hamill JD. RNAi-mediated down-regulation of ornithine decarboxylase (ODC) impedes wound-stress stimulation of anabasine synthesis in Nicotiana glauca. Phytochemistry. 2013 Feb;86:21-8. doi: 10.1016/j.phytochem.2012.10.016. Epub 2012 Nov 22. PubMed PMID: 23177980. 18: Xue Y, Limay-Rios V, Smith J, Baute T, Forero LG, Schaafsma A. Quantifying Neonicotinoid Insecticide Residues Escaping during Maize Planting with Vacuum Planters. Environ Sci Technol. 2015 Nov 3;49(21):13003-11. doi: 10.1021/acs.est.5b03753. Epub 2015 Oct 13. PubMed PMID: 26437361. 19: Matera C, Quadri M, Sciaccaluga M, Pomè DY, Fasoli F, De Amici M, Fucile S, Gotti C, Dallanoce C, Grazioso G. Modification of the anabaseine pyridine nucleus allows achieving binding and functional selectivity for the α3β4 nicotinic acetylcholine receptor subtype. Eur J Med Chem. 2016 Jan 27;108:392-405. doi: 10.1016/j.ejmech.2015.11.045. Epub 2015 Dec 5. PubMed PMID: 26706350. 20: Funayama S. [Tree tobacco Nicotiana glauca]. Chudoku Kenkyu. 2014 Mar;27(1):24-5. Japanese. PubMed PMID: 24724355.