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MedKoo Cat#: 531004 | Name: Arecoline Hydrobromide
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Description:

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

Arecoline Hydrobromide is a muscarinic and nicotinic acetylcholine receptor agonist. Results indicate that the effect of arecoline on rat hepaticdoes not involve transcriptional activation of the gene, but largely involves the stabilization of CYP2E1 protein against degradation or increased efficiency of CYP2E1 mRNA translation, and additionally involve the post- ranslational modification of CYP2E1 protein. Furthermore, the CYP2E1 response is fairly equal among the different species, the induction of rat hepatic CYP2E1 by arecoline suggests that there is a risk of metabolic interaction among the substrate drugs of CYP2E1 in betel-quid use human.

Chemical Structure

Arecoline Hydrobromide
CAS#300-08-3 (HBr)

Theoretical Analysis

MedKoo Cat#: 531004

Name: Arecoline Hydrobromide

CAS#: 300-08-3 (HBr)

Chemical Formula: C8H14BrNO2

Exact Mass: 0.0000

Molecular Weight: 236.11

Elemental Analysis: C, 40.70; H, 5.98; Br, 33.84; N, 5.93; O, 13.55

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
2g USD 400.00 2 Weeks
5g USD 650.00 2 Weeks
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Related CAS #
300-08-3 (HBr) 63-75-2 (free) 61-94-9 (HCl)
Synonym
Arecoline Hydrobromide, Arecoline HBr, NSC 56321, NSC56321, NSC-56321, Arecoline
IUPAC/Chemical Name
methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrobromide
InChi Key
AXOJRQLKMVSHHZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H13NO2.BrH/c1-9-5-3-4-7(6-9)8(10)11-2;/h4H,3,5-6H2,1-2H3;1H
SMILES Code
O=C(C1=CCCN(C)C1)OC.Br
Appearance
White to light yellow crystalline powder.
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

Preparing Stock Solutions

The following data is based on the product molecular weight 236.11 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
1: Fan J, Lin R, Xia S, Chen D, Elf SE, Liu S, Pan Y, Xu H, Qian Z, Wang M, Shan C, Zhou L, Lei QY, Li Y, Mao H, Lee BH, Sudderth J, DeBerardinis RJ, Zhang G, Owonikoko T, Gaddh M, Arellano ML, Khoury HJ, Khuri FR, Kang S, Doetsch PW, Lonial S, Boggon TJ, Curran WJ, Chen J. Tetrameric Acetyl-CoA Acetyltransferase 1 Is Important for Tumor Growth. Mol Cell. 2016 Dec 1;64(5):859-874. doi: 10.1016/j.molcel.2016.10.014. Epub 2016 Nov 17. PubMed PMID: 27867011; PubMed Central PMCID: PMC5135630. 2: Dakkak A, El Berbri I, Petavy AF, Boué F, Bouslikhane M, Fassi Fihri O, Welburn S, Ducrotoy MJ. Echinococcus granulosus infection in dogs in Sidi Kacem Province (North-West Morocco). Acta Trop. 2017 Jan;165:26-32. doi: 10.1016/j.actatropica.2016.07.007. Epub 2016 Jul 18. PubMed PMID: 27436811. 3: Huang XT, Xiao RM, Wang MF, Wang JJ, Chen Y. [Induction of rat hepatic CYP2E1 expression by arecoline in vivo]. Yao Xue Xue Bao. 2016 Jan;51(1):153-6. Chinese. PubMed PMID: 27405178. 4: Wei X, Zhang J, Niu J, Zhou X, Li J, Li B. Evaluation of arecoline hydrobromide toxicity after a 14-day repeated oral administration in Wistar rats. PLoS One. 2015 Apr 16;10(4):e0120165. doi: 10.1371/journal.pone.0120165. eCollection 2015. PubMed PMID: 25880067; PubMed Central PMCID: PMC4399984. 5: Saha I, Das J, Maiti B, Chatterji U. A protective role of arecoline hydrobromide in experimentally induced male diabetic rats. Biomed Res Int. 2015;2015:136738. doi: 10.1155/2015/136738. Epub 2015 Jan 28. PubMed PMID: 25695047; PubMed Central PMCID: PMC4324734. 6: Li B, Zhou XZ, Li JY, Yang YJ, Niu JR, Wei XJ, Liu XW, Li JS, Zhang JY. Determination and pharmacokinetic studies of arecoline in dog plasma by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Oct 15;969:12-8. doi: 10.1016/j.jchromb.2014.07.043. Epub 2014 Aug 8. PubMed PMID: 25140901. 7: Run-mei X, Jun-jun W, Jing-ya C, Li-juan S, Yong C. Effects of arecoline on hepatic cytochrome P450 activity and oxidative stress. J Toxicol Sci. 2014 Aug;39(4):609-14. PubMed PMID: 25056785. 8: Kravchenko EV, Ol'gomets LM. [Influence of changes in the state of brain neurotransmitter and peptidergic systems on circadian rhythms and behavior of rats]. Zh Vyssh Nerv Deiat Im I P Pavlova. 2012 Jul-Aug;62(4):453-64. Russian. PubMed PMID: 23035562. 9: Wu M, Xing G, Qi X, Feng C, Liu M, Gong L, Luan Y, Ren J. Assessment of the mutagenic potential of arecoline in gpt delta transgenic mice. Mutat Res. 2012 Oct 9;748(1-2):65-9. doi: 10.1016/j.mrgentox.2012.07.001. Epub 2012 Jul 11. PubMed PMID: 22796562. 10: Zhao XY, Liu YQ, Fu YC, Xu B, Gao JL, Zheng XQ, Lin M, Chen MY, Li Y. Frequency- and state-dependent blockade of human ether-a-go-go-related gene K+ channel by arecoline hydrobromide. Chin Med J (Engl). 2012 Mar;125(6):1068-75. PubMed PMID: 22613533. 11: Kraziński BE, Radecki J, Radecka H. Surface plasmon resonance based biosensors for exploring the influence of alkaloids on aggregation of amyloid-β peptide. Sensors (Basel). 2011;11(4):4030-42. doi: 10.3390/s110404030. Epub 2011 Apr 6. PubMed PMID: 22163834; PubMed Central PMCID: PMC3231330. 12: Grabowska I, Radecka H, Burza A, Radecki J, Kaliszan M, Kaliszan R. Association constants of pyridine and piperidine alkaloids to amyloid beta peptide determined by electrochemical impedance spectroscopy. Curr Alzheimer Res. 2010 Mar;7(2):165-72. PubMed PMID: 19715547. 13: Lahmar S, Sarciron ME, Rouiss M, Mensi M. Echinococcus granulosus and other intestinal helminths in semi-stray dogs in Tunisia: infection and re-infection rates. Tunis Med. 2008 Jul;86(7):657-64. PubMed PMID: 19472727. 14: Malviya M, Kumar YC, Asha D, Chandra JN, Subhash MN, Rangappa KS. Muscarinic receptor 1 agonist activity of novel N-arylthioureas substituted 3-morpholino arecoline derivatives in Alzheimer's presenile dementia models. Bioorg Med Chem. 2008 Aug 1;16(15):7095-101. doi: 10.1016/j.bmc.2008.06.053. Epub 2008 Jul 2. PubMed PMID: 18640043. 15: Kumar YC, Malviya M, Chandra JN, Sadashiva CT, Kumar CS, Prasad SB, Prasanna DS, Subhash MN, Rangappa KS. Effect of novel N-aryl sulfonamide substituted 3-morpholino arecoline derivatives as muscarinic receptor 1 agonists in Alzheimer's dementia models. Bioorg Med Chem. 2008 May 1;16(9):5157-63. doi: 10.1016/j.bmc.2008.03.019. Epub 2008 Mar 8. PubMed PMID: 18359231. 16: Buccafusco JJ, Bain JN. A 24-h access I.V. self-administration schedule of morphine reinforcement and the estimation of recidivism: Pharmacological modification by arecoline. Neuroscience. 2007 Nov 9;149(3):487-98. Epub 2007 Jul 21. PubMed PMID: 17916413. 17: Lahmar S, Lahmar S, Boufana B, Bradshaw H, Craig PS. Screening for Echinococcus granulosus in dogs: Comparison between arecoline purgation, coproELISA and coproPCR with necropsy in pre-patent infections. Vet Parasitol. 2007 Mar 31;144(3-4):287-92. Epub 2006 Nov 27. PubMed PMID: 17125928. 18: Banks DJ, Copeman DB, Skerratt LF. Echinococcus granulosus in northern Queensland. 2. Ecological determinants of infection in beef cattle. Aust Vet J. 2006 Sep;84(9):308-11. PubMed PMID: 16958625. 19: Naidich A, McManus DP, Canova SG, Gutierrez AM, Zhang W, Guarnera EA, Rosenzvit MC. Patent and pre-patent detection of Echinococcus granulosus genotypes in the definitive host. Mol Cell Probes. 2006 Feb;20(1):5-10. Epub 2005 Oct 14. PubMed PMID: 16226869. 20: Sánchez-Santed F, Cañadas F, Flores P, López-Grancha M, Cardona D. Long-term functional neurotoxicity of paraoxon and chlorpyrifos: behavioural and pharmacological evidence. Neurotoxicol Teratol. 2004 Mar-Apr;26(2):305-17. PubMed PMID: 15019964.