每周分子 | Molecule of the Week

Original ACS美国化学会 ACS美国化学会 2022-07-01

收录于合集 #每周分子 110个

每周分子：槟榔碱

Molecule of the Week: Arecoline

槟榔碱是在槟榔种子中被发现的一种生物碱酯，又名Areca palm, 学名为Areca catechu。“槟榔果”这个词有点让人困惑，因为南亚和东南亚人经常把槟榔和来自同名藤蔓植物(胡椒槟榔)槟榔叶一起咀嚼。但这两种植物在生物学上没有亲缘关系。

槟榔碱自1891年由德国药剂师E.Jahns从儿茶籽中分离出来后就被人们所知。1926年，德国耶拿大学的Fritz Chemnitius报道了槟榔碱的首次合成。槟榔碱是一种中等强度的碱，pKb值为6.8。它能与水和大多数有机溶剂混溶。与槟榔碱酯相对应的羧酸被称为水解槟榔碱，也存在于槟榔果中。

人们食用槟榔果是因为它们能提供一种类似于尼古丁引起的“快感”。然而，槟榔碱作用的受体与尼古丁不同：毒蕈碱(而非烟碱)乙酰胆碱受体(特别是M₄)可能是影响副交感神经系统的原因。和尼古丁相似，槟榔碱会让人上瘾。咀嚼槟榔也很危险，因为它们含有可能导致口腔和食道癌症的成分。

槟榔碱信息速览

CAS 登记号	63-75-2
SciFinder命名	3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl, methyl ester
分子式	C₈H₁₃NO₂
摩尔质量	155.19 g/mol
外观	无色油状液体
熔点	27 ºC
沸点	209 ºC
水溶性	混溶

槟榔碱危害信息

GHS*分类：急性毒性，口服，分类4
H302-吞食有害

【关于每周分子】

自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社 (CAS) 提供的SciFinder中的CAS REGISTRY获取“每周分子”的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至motw@acs.org推荐您感兴趣的分子吧。

Arecoline is an alkaloid ester found in the seeds of the betel nut palm, which is also called areca palm from its scientific name, Areca catechu. The term “betel nut” is a bit confusing because South and Southeast Asians often chew it along with betel leaf from the vine of the same name (Piper betle). The two plants are not biologically related.

Arecoline has been known since 1891, when German pharmacist E. Jahns isolated it from A. catechu seeds. The first synthesis was reported by Fritz Chemnitius at Jena University (Germany) in 1926. It is a moderately strong base, with a pKb value of 6.8. It is miscible with water and most organic solvents. The carboxylic acid corresponding to the arecoline ester is called arecaidine; it also exists in betel nuts.

People consume betel nuts because they provide a “high” similar to that caused by nicotine. Arecoline, however, acts on different receptors than does nicotine: muscarinic (rather than nicotinic) acetylcholine receptors, especially M₄, which may be the cause of its effects on the parasympathetic nervous system. Similarly to nicotine, arecoline is addictive. Chewing betel nuts is also dangerous because they contain ingredients that can cause cancers of the mouth and the esophagus.

Arecolinefast facts

CAS Reg. No.	63-75-2
SciFinder nomenclature	3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl, methyl ester
Empirical formula	C₈H₁₃NO₂
Molar mass	155.19 g/mol
Appearance	Colorless oily liquid
Melting point	27 ºC
Boiling point	209 ºC
Water solubility	MIscible

Arecoline hazard information

Hazard class: Acute toxicity, oral, category 4
H302 - Harmful if swallowed

About Molecule of the Week

MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using SciFinder. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.

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