CAS 63-75-2 Arecoline (HCID 2230)

Names & identifiers

Preferred name: Arecoline
IUPAC: methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
English name: arecoline
Molecular formula: C8H13NO2
Molecular weight: 155.19

Names & synonyms

arecoline63-75-2ArecolinArecalineArecholineMethylarecaidenMethylarecaidinArekolinArecoline baseArecaidine methyl estermethyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester

Show more names

NSC 56321ArecaidinMethyl arecaidinMethylarecaidineEphedrine alkaloidarecoline ISO 9001：2015 REACH

ArecholinMethyl N-methyltetrahydronicotinatemethyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylateDTXSID3022617N-Methyltetrahydronicotinic acid, methyl esterMethyl 1,2,5,6-tetrahydro-1-methylnicotinateMethyl N-methyl-1,2,5,6-tetrahydronicotinateNSC-56321

Database identifiers

CAS: 63-75-2
PubChem CID: 2230
DTXSID: DTXSID3022617
ChEMBL: CHEMBL7303
ChEBI: CHEBI:2814
UNII: 4ALN5933BH
EC Number: 200-565-5
Nikkaji: J4.830E

Properties

Computed structural properties

XLogP: 0.3
Topological polar surface area: 29.5 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 11
Formal charge: 0
Complexity: 187

Experimental & physicochemical properties

LogP · 2 items

0.35

0.350

LogS0.81

Solubility · 2 items

1000000

1.00E+06 mg/L @ 25 °C (exp)

Boiling Point · 2 items

209

209.00 °C. @ 760.00 mm Hg

Melting Point< 25 °C

Dissociation Constants · 2 items

7.64

7.16

Physicochemical properties

Melting point: 25 ℃ · <25℃
Boiling point: 209 ℃ · 209℃
Density: 1.0504 g/cm3 · 1.0504 g/cm3 (20 ºC)
refractive index: 1.486 · 1.4860 (589.3 nm 20℃)
storage temp.: Sealed in dry,Room Temperature
solubility: Chloroform (Sparingly), Methanol (Slightly)
form: Oil
pka: 6.84 · 6.84(at 25℃)
color: Oily liquid
InChI: InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
InChIKey: HJJPJSXJAXAIPN-UHFFFAOYSA-N
SMILES: C1N(C)CCC=C1C(OC)=O
LogP: 0.35 · 0.350
FDA UNII: 4 ALN5933BH · 4ALN5933BH
Toxicity: 50 in · LD50 in mice, dogs (mg/kg): 100, 5 s.c. (Burrows)

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Danger

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H340 (50%): May cause genetic defects [Danger Germ cell mutagenicity]；H351 (50%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P264, P264+P265, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 2 reports by companies.；There is 1 notification provided by 1 of 2 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationHazard Traits - Carcinogenicity；Authoritative List - IARC Carcinogens - 2B；Report - regardless of intended function of ingredient in the product

Hazard Classes and CategoriesSkin Irrit. 2 (50%)；Eye Irrit. 2 (50%)；Muta. 1A (50%)；Carc. 2 (50%)

Toxicology

Health EffectsPupillary constriction, bronchial constriction.

Exposure RoutesIngestion

Toxicity Summary · 1 item

Arecoline is the primary active ingredient responsible for the central nervous system effects of the areca nut. Arecoline has been compared to nicotine; however, nicotine acts primarily on the nicotinic acetylcholine receptor. Arecoline is known to be a partial agonist of muscarinic acetylcholine M1, M2, M3 receptors and M4, which is believed to be the primary cause of its parasympathetic effects (such as pupillary constriction, bronchial constriction, etc.). (Wikipedia) Arecoline is cytotoxic to human gingival fibroblasts at a concentration higher than 50 μg/ml by depleting intracellular thiols and inhibiting mitochondrial activity (P<0.05). In addition, the cells displayed a marked arrest at G2/M phase in a dose-dependent manner. (A15351)

Carcinogen Classification · 6 items

Arecoline

Group 2B: Possibly carcinogenic to humans

Volume 128: (2021) Acrolein, Crotonaldehyde, and Arecoline

2021 online

2020

Not listed by IARC.

Toxicity DataLD50: 100 mg/kg, administered subcutaneously in mouse (Wikipedia)

Regulatory information

Regulatory InformationHazard Traits - Carcinogenicity；Authoritative List - IARC Carcinogens - 2B；Report - regardless of intended function of ingredient in the product

Safety data

Toxicity: LD50 in mice, dogs (mg/kg): 100, 5 s.c. (Burrows)

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationDrugs that bind to and activate cholinergic receptors.

Cellular LocationsCytoplasm；Extracellular

Uses & manufacturing

Uses · 1 item

Arecoline is found in nuts. Arecoline is isolated from betel nuts Arecoline is an alkaloid natural product found in the areca nut, the fruit of the areca palm (Areca catechu). Since one of the hallmarks of Alzheimer's disease is a cognitive decline, arecoline was suggested as a treatment to slow down this process and arecoline administered via i.v. Arecoline has also been used medicinally as an antihelmintic (a drug against parasitic worms).

Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan

Applications · 4 items

DescriptionAreca catechu L. (Bin Lang), a palm plant native to Malaysia, is mainly distributed in tropical regions of Asia and the Americas. Arecoline is extracted from dry mature seeds of areca. The mature seeds of areca are 3–5 cm in diameter, with fibrous peel and a seed, namely, areca nut. The endosperm of areca nut is hard, with grayish-brown spots. Areca nut is harvested from August to November every year before the fruit is fully mature. The seeds are peeled, boiled, and cut into thin slices. The dried slices are brown or black, and it is an important medicine in traditional Chinese medicine. Areca nut is the raw materials of catechu. Areca nut was used as anthelmintics with arecoline as the main alkaloid in it.

HistoryArecoline, an alkaloid extracted from Areca catechu L., is first reported by Jahns in 1888. Mujumdar found that there were at least six kinds of alkaloids in areca, including arecoline, arecaidine, guavacoline, and guavacine. The content of arecoline in the fresh fruit of areca was 0.3–0.63% as determined with HPLC .It has been found first that arecoline has the effect of antiparasite and is promoting the motility of the gastrointestinal smooth muscle. It activates the M and N cholinergic receptors, excites the nervous system, promotes the body excitability, and improves the ability of learning and memory .

UsesArecoline has shown regulatory properties of controlling plasminogen activator inhibitor-1 expression in human buccal mucosa fibroblasts.

UsesArecoline is a cholinergic alkaloid from seeds of the betel nut palm Areca catechu. It 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. It has been used as a euphoriant in the Pacific Islands.

Upstream & downstream products

Upstream raw materials

Downstream products

Pyridine, 3-(3-ethyl-1,2,4-oxadiazol-5-yl)-1,2,5,6-tetrahydro-1,2,3,6-tetrahydro-5-(3-methyl-1,2,4-oxadiazol-5-yl)Pyridine

Suppliers100 total

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]

陕西科贝莱药物研发有限公司13119135307 · [email protected]

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]

成都曼思特生物科技有限公司18010516991 · [email protected]

南京普怡生物科技有限公司13814510036 · [email protected]

Additional notes · 1 item

DefinitionChEBI: Arecoline is a tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine. It has a role as a muscarinic agonist and a metabolite. It is a tetrahydropyridine, an enoate ester, a pyridine alkaloid and a methyl ester.