Arecoline (HCID 2230)

名称と識別子

優先名称: Arecoline
IUPAC: methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
現地名: アレコリン
英語名: arecoline
分子式: C8H13NO2
分子量: 155.19

名称と別名

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

名称をさらに表示

1-メチル-1,2,5,6-テトラヒドロピリジン-3-カルボン酸メチル1,2,5,6-テトラヒドロ-1-メチル-3-ピリジンカルボン酸メチル1-メチル-1,2,5,6-テトラヒドロ-3-ピリジンカルボン酸メチル1,2,5,6-テトラヒドロ-1-メチルニコチン酸メチル1-メチルピペリジン-3-エン-3-カルボン酸メチル1-メチル-1,2,5,6-テトラヒドロニコチン酸メチルアレコリンメチル 1-メチル-1,2,5,6-テトラヒドロピリジン-3-カルボキシラート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

データベース識別子

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

物性

構造計算による物性

XLogP: 0.3
極性表面積: 29.5 Å²
水素結合供与体数: 0
水素結合受容体数: 3
回転可能結合数: 2
重原子数: 11
形式電荷: 0
複雑度: 187

実験および物理化学的性質

LogP · 2 件

0.35

0.350

LogS0.81

Solubility · 2 件

1000000

1.00E+06 mg/L @ 25 °C (exp)

Boiling Point · 2 件

209

209.00 °C. @ 760.00 mm Hg

Melting Point< 25 °C

Dissociation Constants · 2 件

7.64

7.16

物理化学的性質

融点: 25 ℃ · <25℃
沸点: 209 ℃ · 209℃
比重(密度): 1.0504 g/cm3 · 1.0504 g/cm3 (20 ºC)
屈折率: 1.486 · 1.4860 (589.3 nm 20℃)
貯蔵温度: Sealed in dry,Room Temperature
溶解性: クロロホルム（少量）、メタノール（少量）
外見: 油
酸解離定数(Pka): 6.84 · 6.84(at 25℃)
色: 油性液体
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

化学的性質

化学的特性Oily Liquid

安全と法規制

GHS分類

GHS Classification · 6 件

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.

危険有害性情報

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%)

毒性情報

Health EffectsPupillary constriction, bronchial constriction.

Exposure RoutesIngestion

Toxicity Summary · 1 件

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 件

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)

法規制情報

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

安全データ

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

化学と産業

薬理情報

MeSH Pharmacological ClassificationDrugs that bind to and activate cholinergic receptors.

Cellular LocationsCytoplasm；Extracellular

用途と製造

Uses · 1 件

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

応用分野 · 4 件

解説C8H13NO2(155.20)．アレコリンは，ヤシ科ビンロウジュAreca catechuの果実に含まれるピリジンアルカロイドの一つ．アレカイジンのメチルエステル．黄色の油状液体．沸点209 ℃．水，エタノール，メタノール，エーテルに易溶，クロロホルムに可溶．家畜の条虫駆除剤として用いられる．LD50 100 mg/kg(マウス，皮下)．森北出版「化学辞典（第2版）

説明Areca 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.

来歴Arecoline, 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 .

使用Arecoline 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.

上流・下流製品情報

上流原料

下流製品

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

サプライヤー50 社

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]

補足説明 · 1 件

定義ChEBI: 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.