Arecoline 分子结构式
HCID2230

Arecoline

methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate

C8H13NO2155.19 g/molCAS 63-75-2

IDENTITY

结构与身份

标准SMILES
COC(=O)C1=CCCN(C)C1
InChIKey
HJJPJSXJAXAIPN-UHFFFAOYSA-N
分子式
C8H13NO2
平均分子量
155.19 g/mol
单同位素质量
155.09462866

COMPUTED

结构计算性质

已同步
XLogP
0.3
极性表面积
29.5 Ų
氢键供体
0
氢键受体
3
可旋转键
2
重原子
11
形式电荷
0
复杂度
187

PROPERTIES

实验与物化性质

LogP

0.35

0.350

LogS

0.81

Solubility

1000000

1.00E+06 mg/L @ 25 °C (exp)

Boiling Point

209

209.00 °C. @ 760.00 mm Hg

Melting Point

< 25 °C

Dissociation Constants

7.64

7.16

Kovats Retention Index

1195

1236.1

GHS

GHS分类

GHS Classification

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.

HAZARDS

危害信息

Regulatory Information

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

Hazard Classes and Categories

Skin Irrit. 2 (50%);Eye Irrit. 2 (50%);Muta. 1A (50%);Carc. 2 (50%)

TOXICITY

毒理信息

Health Effects

Pupillary constriction, bronchial constriction.

Exposure Routes

Ingestion

Toxicity Summary

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

Arecoline

Group 2B: Possibly carcinogenic to humans

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

2021 online

2020

Not listed by IARC.

Toxicity Data

LD50: 100 mg/kg, administered subcutaneously in mouse (Wikipedia)

REGULATORY

法规信息

Regulatory Information

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

PHARMACOLOGY

药理信息

MeSH Pharmacological Classification

Drugs that bind to and activate cholinergic receptors.

Cellular Locations

Cytoplasm;Extracellular

USES

用途与制造

Uses

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 Classification

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

ALIASES

名称与别名

共 145 条
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 esterArecholinMethyl 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

REACTIONS

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