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MedKoo Cat#: 573229 | Name: Arecoline
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Description:

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

Arecoline is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. Arecoline inhibits myogenic differentiation and acetylcholine receptor cluster formation of C2C12 myoblasts.

Chemical Structure

Arecoline
CAS#63-75-2 (free)

Theoretical Analysis

MedKoo Cat#: 573229

Name: Arecoline

CAS#: 63-75-2 (free)

Chemical Formula: C8H13NO2

Exact Mass: 155.0946

Molecular Weight: 155.20

Elemental Analysis: C, 61.91; H, 8.44; N, 9.03; O, 20.62

Price and Availability

Size Price Availability Quantity
100mg USD 550.00 4 Weeks
250mg USD 950.00 4 Weeks
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Related CAS #
300-08-3 (HBr) 63-75-2 (free) 61-94-9 (HCl)
Synonym
Arecoline
IUPAC/Chemical Name
3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester
InChi Key
HJJPJSXJAXAIPN-UHFFFAOYSA-N
InChi Code
1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
SMILES Code
C1[N@@](CC(=CC1)C(OC)=O)C
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
>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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 155.20 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: Volgin AD, Bashirzade A, Amstislavskaya TG, Yakovlev OA, Demin KA, Ho YJ, Wang D, Shevyrin VA, Yan D, Tang Z, Wang J, Wang M, Alpyshov ET, Serikuly N, Wappler-Guzzetta EA, Lakstygal AM, Kalueff AV. DARK Classics in Chemical Neuroscience: Arecoline. ACS Chem Neurosci. 2019 May 15;10(5):2176-2185. doi: 10.1021/acschemneuro.8b00711. Epub 2019 Feb 21. PMID: 30664352. 2: Liu YJ, Peng W, Hu MB, Xu M, Wu CJ. The pharmacology, toxicology and potential applications of arecoline: a review. Pharm Biol. 2016 Nov;54(11):2753-2760. doi: 10.3109/13880209.2016.1160251. Epub 2016 Apr 5. PMID: 27046150. 3: Oliveira NG, Ramos DL, Dinis-Oliveira RJ. Genetic toxicology and toxicokinetics of arecoline and related areca nut compounds: an updated review. Arch Toxicol. 2021 Feb;95(2):375-393. doi: 10.1007/s00204-020-02926-9. Epub 2020 Oct 24. PMID: 33097969. 4: Babikian PV, Thompson HS. Arecoline miosis. Am J Ophthalmol. 1984 Oct 15;98(4):514-5. doi: 10.1016/0002-9394(84)90143-0. PMID: 6486230. 5: Li YX, Hsiao CH, Chang YF. N-acetyl cysteine prevents arecoline-inhibited C2C12 myoblast differentiation through ERK1/2 phosphorylation. PLoS One. 2022 Jul 28;17(7):e0272231. doi: 10.1371/journal.pone.0272231. PMID: 35901044; PMCID: PMC9333315. 6: Ho TJ, Chi-Kang Tsai B, Kuo CH, Luk HN, Day CH, Jine-Yuan Hsieh D, Chen RJ, Kuo WW, Kumar VB, Yao CH, Huang CY. Arecoline induces cardiotoxicity by upregulating and activating cardiac hypertrophy-related pathways in Sprague- Dawley rats. Chem Biol Interact. 2022 Feb 25;354:109810. doi: 10.1016/j.cbi.2022.109810. Epub 2022 Jan 7. PMID: 34999050. 7: Li X, Gao Y, Chen W, Gu Y, Song J, Zhang J, Ai Y. N6-methyladenosine modification contributes to arecoline-mediated oral submucosal fibrosis. J Oral Pathol Med. 2022 May;51(5):474-482. doi: 10.1111/jop.13292. Epub 2022 Apr 4. PMID: 35377493. 8: Cheng X, Jiang JM, Wang CY, Zou W, Zhang P, Tang XQ. Hydrogen sulfide prevents arecoline-induced neurotoxicity via promoting leptin/leptin receptor signaling pathway. Cell Biol Int. 2022 Sep;46(9):1355-1366. doi: 10.1002/cbin.11850. Epub 2022 Jul 12. PMID: 35819076. 9: IARC Monographs Vol 128 group. Carcinogenicity of acrolein, crotonaldehyde, and arecoline. Lancet Oncol. 2021 Jan;22(1):19-20. doi: 10.1016/S1470-2045(20)30727-0. Epub 2020 Nov 26. PMID: 33248467. 10: Ko AM, Tu HP, Ko YC. Systematic Review of Roles of Arecoline and Arecoline N-Oxide in Oral Cancer and Strategies to Block Carcinogenesis. Cells. 2023 Apr 21;12(8):1208. doi: 10.3390/cells12081208. PMID: 37190117; PMCID: PMC10137008. 11: Lin WY, Tsai BC, Day CH, Chiu PL, Chen RJ, Chen MY, Padma VV, Luk HN, Lee HC, Huang CY. Arecoline induces heart injure via Fas/Fas ligand apoptotic pathway in heart of Sprague-Dawley rat. Environ Toxicol. 2021 Aug;36(8):1567-1575. doi: 10.1002/tox.23153. Epub 2021 Apr 30. PMID: 33929070. 12: Yang HW, Yu CC, Hsieh PL, Liao YW, Chu PM, Yu CH, Fang CY. Arecoline enhances miR-21 to promote buccal mucosal fibroblasts activation. J Formos Med Assoc. 2021 Apr;120(4):1108-1113. doi: 10.1016/j.jfma.2020.10.019. Epub 2020 Nov 13. PMID: 33191095. 13: Tu HF, Chen MY, Lai JC, Chen YL, Wong YW, Yang CC, Chen HY, Hsia SM, Shih YH, Shieh TM. Arecoline-regulated ataxia telangiectasia mutated expression level in oral cancer progression. Head Neck. 2019 Aug;41(8):2525-2537. doi: 10.1002/hed.25718. Epub 2019 Feb 28. PMID: 30821076. 14: Ozenil M, Pacher K, Balber T, Vraka C, Roller A, Holzer W, Spreitzer H, Mitterhauser M, Wadsak W, Hacker M, Pichler V. Enhanced arecoline derivatives as muscarinic acetylcholine receptor M1 ligands for potential application as PET radiotracers. Eur J Med Chem. 2020 Oct 15;204:112623. doi: 10.1016/j.ejmech.2020.112623. Epub 2020 Jul 19. PMID: 32717485. 15: Nithiyanantham S, Arumugam S, Hsu HT, Chung CM, Lee CP, Tsai MH, Yeh KT, Luo SY, Ko YC. Arecoline N-oxide initiates oral carcinogenesis and arecoline N-oxide mercapturic acid attenuates the cancer risk. Life Sci. 2021 Apr 15;271:119156. doi: 10.1016/j.lfs.2021.119156. Epub 2021 Feb 3. PMID: 33548289. 16: Pi M, Yue K, Ma B, Tian X, Liu W, Sun B, Shu X. Susceptibility to arecoline in male C57BL/6 J mice correlates with age factor. Behav Brain Res. 2023 Jul 26;450:114493. doi: 10.1016/j.bbr.2023.114493. Epub 2023 May 11. PMID: 37178776. 17: Li WD, Zang CJ, Yin S, Shen W, Sun QY, Zhao M. Metformin protects against mouse oocyte apoptosis defects induced by arecoline. Cell Prolif. 2020 Jul;53(7):e12809. doi: 10.1111/cpr.12809. Epub 2020 Jun 17. PMID: 32557964; PMCID: PMC7377942. 18: Chen Q, Jiang Z, Zhang J, Cao L, Chen Z. Arecoline hydrobromide enhances jejunum smooth muscle contractility via voltage-dependent potassium channels in W/Wv mice. Physiol Res. 2021 Jul 12;70(3):437-446. doi: 10.33549/physiolres.934557. Epub 2021 May 12. PMID: 33982580; PMCID: PMC8820561. 19: Zhou ZS, Li M, Gao F, Peng JY, Xiao HB, Dai LX, Lin SR, Zhang R, Jin LY. Arecoline suppresses HaCaT cell proliferation through cell cycle regulatory molecules. Oncol Rep. 2013 Jun;29(6):2438-44. doi: 10.3892/or.2013.2360. Epub 2013 Mar 22. PMID: 23525646. 20: Kuo TM, Luo SY, Chiang SL, Lee CP, Liu YF, Chang JG, Tsai MH, Ko YC. Arecoline induces TNF-alpha production and Zonula Occludens-1 redistribution in mouse Sertoli TM4 cells. J Biomed Sci. 2014 Sep 9;21(1):93. doi: 10.1186/s12929-014-0093-z. PMID: 25200553; PMCID: PMC4256803.