Arecoline - Moligand™, ≥98% , Agonist of M 1 receptor;Agonist of M 2 receptor;Agonist of M 3 receptor;Agonist of M 4 receptor;Agonist of M 5 receptor, CAS No.63-75-2, Agonist of M 1 receptor;Agonist of M 2 receptor;Agonist of M 3 receptor;Agonist of M 4 receptor;Agonist of M 5 receptor

CAS: 63-75-2 Cat. No.: A348021 Molecular Weight: 155.19 EC Number: 200-565-5

GRADE & PURITY Moligand™, ≥98%

Synonyms

Lopac0_000049 | Methyl N-methyltetrahydronicotinate | Q423515 | Spectrum_000055 | BSPBio_000324 | L000795 | 63-75-2 (free) | Arecholine | DTXCID502617 | KBioSS_000435 | Methyl 1,2,5, 6-tetrahydro-1-methylnicotinate | Arecaidine methyl ester | Prestwick1_0

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Overview

A cholinergic alkaloid from seeds of the betel nut palm Areca catechu. Anthelmintic (Cestodes); cathartic.

Specifications

Synonyms

Lopac0_000049 | Methyl N-methyltetrahydronicotinate | Q423515 | Spectrum_000055 | BSPBio_000324 | L000795 | 63-75-2 (free) | Arecholine | DTXCID502617 | KBioSS_000435 | Methyl 1, 2, 5, 6-tetrahydro-1-methylnicotinate | Arecaidine methyl ester | Prestwick1_0

Specifications & Purity

Moligand™, ≥98%

Storage

Store at 2-8°C, Protected from light

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of M 1 receptor;Agonist of M 2 receptor;Agonist of M 3 receptor;Agonist of M 4 receptor;Agonist of M 5 receptor

Purity

≥98%

Product Properties

• pKa: pKa: 6.84
• Ki Data: Muscarinic acetylcholine receptor M1: Ki= 3.33 nM (Mus musculus); Muscarinic acetylcholine receptor: Ki= 5.3 nM (rat); Muscarinic acetylcholine receptor M3: Ki= 7.4 nM (rat); Muscarinic acetylcholine receptor M4: Ki= 7.4 nM (rat)

Names and Identifiers

• Pubchem Sid: 488179679
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488179679
• Canonical Smiles: CN1CCC=C(C1)C(=O)OC
• IUPAC Name: methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
• InChIKey: HJJPJSXJAXAIPN-UHFFFAOYSA-N
• INCHI: 1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
• Isomeric SMILES: CN1CCC=C(C1)C(=O)OC
• Alternate CAS: 300-08-3
• Molecular Weight: 155.19
• Reaxy-Rn: 123045
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=123045&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Not available
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Alkaloids and derivatives
• Alternative Parents: Hydropyridines Methyl esters Enoate esters Trialkylamines Amino acids and derivatives Monocarboxylic acids and derivatives Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Alkaloid or derivatives - Hydropyridine - Methyl ester - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Amino acid or derivatives - Carboxylic acid ester - Tertiary amine - Tertiary aliphatic amine - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organoheterocyclic compound - Azacycle - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Amine - Organic oxide - Hydrocarbon derivative - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
• External Descriptors: Pyridine alkaloids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CHRM5 Tclin Muscarinic acetylcholine receptor M5 (0 Activities)

Discover Target: CHRM5

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM3 Tclin Muscarinic acetylcholine receptor M3 (2 Activities)

Discover Target: CHRM3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM4 Tclin Muscarinic acetylcholine receptor M4 (2 Activities)

Discover Target: CHRM4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (6 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (3 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM4 Tclin Muscarinic acetylcholine receptor M4 (6041 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM5 Tclin Muscarinic acetylcholine receptor M5 (4677 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SK-N-SH (1499 Activities)

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ABCB11 Tchem Bile salt export pump (2311 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LMNA Tbio Prelamin-A/C (36751 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRNB2 Tclin Neuronal acetylcholine receptor; alpha4/beta2 (3972 Activities)

Discover Target: CHRNB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM3 Tclin Muscarinic acetylcholine receptors; M2 & M3 (708 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptors; M1 & M2 (498 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Plasmodium falciparum (966862 Activities)

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Cavia porcellus (23802 Activities)

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Oryctolagus cuniculus (11301 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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A9 (98 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FTL Ferritin light chain (43324 Activities)

Discover Target: FTL

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Chrm1 Muscarinic acetylcholine receptor (3770 Activities)

Discover Target: Chrm1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Chrna3 Neuronal acetylcholine receptor (756 Activities)

Discover Target: Chrna3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

nAChRalpha5 Nicotinic acetylcholine receptor alpha 5 subunit (134 Activities)

Discover Target: nAChRalpha5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CACNA1C Voltage-dependent L-type calcium channel subunit alpha-1C (242 Activities)

Discover Target: CACNA1C

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water, chloroform, DMSO, and methanol.
• Refractive Index: n20D1.48 (Predicted)
• Boil Point(°C): 209° C
• Melt Point(°C): 27.46° C (Predicted)
• Molecular Weight: 155.190 g/mol
• XLogP3: 0.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 155.095 Da
• Monoisotopic Mass: 155.095 Da
• Topological Polar Surface Area: 29.500 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 187.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Ying Lu, Jianna Yu, Wen Liu, Guoxing Jing, Wenshan Li, Wenjie Liu.  (2022)  Quantitative determination of major alkaloids in areca nut products by high-performance liquid chromatography coupled with ion mobility spectrometry.  JOURNAL OF SEPARATION SCIENCE,  45  (24): (4469-4477).  [PMID:36250424] [10.1002/jssc.202200361]

2. Yin Lifen, Wang Xiao.  (2024)  Curcumin Alleviates Arecoline-induced Oral Submucous Fibrosis via the FOSL1/MAPK8 Axis.  CELL BIOCHEMISTRY AND BIOPHYSICS,      [PMID:39674970] [10.1007/s12013-024-01633-x]

3. Kaiping Xiang, Bing Wang, Lanying Wang, Yunfei Zhang, Hanzeng Li, Yanping Luo.  (2024)  Oxidative Stress, Oxidative Damage, and Cell Apoptosis: Toxicity Induced by Arecoline in Caenorhabditis elegans and Screening of Mitigating Agents.  Toxins,  16  (8): (352).  [PMID:39195762] [10.3390/toxins16080352]

4. Sun Honglan, Yang Chao, Yin Xiaoyunqing, Chen Shizhao, Huang Yuqi, Kuang Huifang, Luo Wen.  (2025)  VHL ameliorates arecoline-induced oral submucosal fibrosis by promoting HDAC6 ubiquitination and blocking NF-κB pathway.  Scientific Reports,  15  (1): (1-12).  [PMID:40038412] [10.1038/s41598-025-91207-5]

5. Yuejie Wu, Fei Wang, Longxiang Gao, Yunfei Zhang, Lanying Wang, Yanping Luo.  (2025)  Evaluation of the Intergenerational Effects of Arecoline on Aedes aegypti via Acute Exposure and Its Role in Inducing the Leg Deformities Involved in Chitin Synthesis Inhibition.  ENVIRONMENTAL TOXICOLOGY,      [PMID:41427474] [10.1002/tox.70013]

6. Ting-Syuan Lin, Jingting Wan, Jingjin He, Shidong Cui, Yun Huang, Bojian Zhang, Hsi-Yuan Huang, Kexin Zhu, Jihang Chen, Tao Zhang, Shangfu Li, Liao Hu, Yongfei Wang, Hsien-Da Huang, Ping Tang, Yang-Chi-Dung Lin.  (2026)  Arecoline as a Novel Scaffold Targeting the ATAD2 Bromodomain for Cell Cycle Modulation.  Pharmaceutics,  18  (3): (324).  [PMID:] [10.3390/pharmaceutics18030324]