アレコリン
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
識別子と物理属性
| CAS No. | 63-75-2 |
|---|---|
| 分子式 | C8H13NO2 |
| 平均分子量 | 155.19 g/mol |
| 単同位体質量 | 155.09462866 g/mol |
| SMILES | COC(=O)C1=CCCN(C)C1 |
| InChIKey | HJJPJSXJAXAIPN-UHFFFAOYSA-N |
| PubChem CID | 2230 |
| ChEMBL | CHEMBL7303 |
| ChEBI | CHEBI:2814 |
| EC No. | 200-565-5 |
| DTXSID | DTXSID3022617 |
| 現地名 | アレコリン |
化学・物理的性質
| XLogP | 0.3 |
|---|---|
| 極性表面積 | 29.5 |
| 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 |
| LogP（分配係数） | 0.350.350 |
| LogS | 0.81 |
| 溶解度 | 10000001.00E+06 mg/L @ 25 °C (exp)クロロホルム（少量）、メタノール（少量） |
| 沸点 | 209209.00 °C. @ 760.00 mm Hg209℃ |
| 融点 | < 25 °C<25℃ |
| Dissociation Constants | 7.647.16 |
| Kovats Retention Index | 11951236.1 |
| 密度 | 1.0504 g/cm3 (20 ºC) |
| 屈折率 | 1.4860 (589.3 nm 20℃) |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 外観・状態 | 油 |
| pKa（酸解離定数） | 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（分配係数） | 0.350 |
化学的特性
Oily Liquid
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.DangerH315 (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. |
|---|---|
| 規制情報 | Hazard Traits - CarcinogenicityAuthoritative List - IARC Carcinogens - 2BReport - 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%) |
| 健康影響 | Pupillary constriction, bronchial constriction. |
| 暴露経路 | Ingestion |
| 毒性の概要 | Arecoline is the primary active ingredient responsible for the central nervous system effects of the areca nut. Arecoline has been compared to nicotinehowever, 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) |
用途
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.