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: 去甲肾上腺素

Molecule of the Week: Norepinephrine

去甲肾上腺素是儿茶酚胺家族中的一种激素和起神经递质作用的天然化合物。它的原名是"noradrenaline"，英国仍使用该名称，美国和世界卫生组织使用的名称是"norepinephrine"。去甲肾上腺素中的"Nor"表明它有母分子肾上腺素的结构，用氢原子代替了N-甲基基团。

根据默克指数，去甲肾上腺素“出现在动物和人类中，是一种人类肾上腺和肾上腺交感神经节后神经元分泌的拟交感神经激素。作为肾上腺激素，它的释放引起血管收缩，从而增加血压。尽管其存在危害(见危害信息表)，但这一特点却促使科学家开发出去甲肾上腺素作为静脉注射药物，用于治疗血压极低的患者。

1945年，卡罗林斯卡研究所(Solna, Sweden)的生理学家Ulf van Euler发现了去甲肾上腺素在体内的作用。他因在神经递质方面的工作而获得1970年诺贝尔生理学或医学奖。

今年早些时候，研究人员报告了以前未知的去甲肾上腺素特性。哈佛大学(剑桥，MA)的Ya-Chieh Hsu及其同事们和其他研究机构使用实验老鼠来确定压力引起的头发脱色的生化原因，他们发现罪魁祸首正是去甲肾上腺素。

但是，当作者们从老鼠身上摘下肾上腺来检测他们的发现时，得到了最大的意外结果：啮齿动物仍然变灰了。研究人员发现，处于压力之下的动物也会从交感神经系统中释放去甲肾上腺素。这种化学物质到达毛囊，耗尽了产生色素的干细胞。

去甲肾上腺素信息速览

CAS 登记号	51-41-2
SciFinder命名	1,2-Benzenediol, 4-[(1R)-2-amino-1-hydroxyethyl]-
分子式	C₈H₁₁NO₃
摩尔质量	169.18 g/mol
外观	白色到褐色晶体；无色微晶
熔点	217 ºC
水溶性	0.85 g/L

去甲肾上腺素危害信息

危险等级*：急性毒性，口服，类别2
H300-吞咽致命
危险等级：急性毒性，皮肤，类别2
H310-与皮肤接触致命
危险等级：急性毒性，吸入，类别1
H330-吸入致命

【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。

Norepinephrine is a natural compound in the catecholamine family that acts as a hormone and neurotransmitter. Its original name was noradrenaline, which is still used in the United Kingdom. The United States and the World Health Organization use norepinephrine. “Nor” in norepinephrine indicates that it has the structure of the parent molecule epinephrine with a hydrogen atom in place of the N-methyl group.

According to the Merck Index, norepinephrine “occurs in animals and [humans] and is a sympathomimetic hormone of both adrenal origin and adrenergic orthosympathetic postganglionic origin in [humans].” As an adrenal hormone, its release triggers vasoconstriction, which increases blood pressure. Despite its hazards (see table), this characteristic led scientists to develop norepinephrine as an intravenous drug for treating patients with very low blood pressure.

Physiologist Ulf van Euler at the Karolinska Institute (Solna, Sweden) discovered norepinephrine’s role in the body in 1945. He shared the 1970 Nobel Prize in Physiology or Medicine for his work on neurotransmitters.

Earlier this year, researchers reported a previously unknown property of norepinephrine. Ya-Chieh Hsu and colleagues at Harvard University (Cambridge, MA) and other research institutions used laboratory mice to determine the underlying biochemical cause of stress-induced hair depigmentation. They found that the culprit is norepinephrine, which is released by mammals’ adrenal glands when animals are under stress.

But the authors’ big surprise came when they removed the adrenal glands from mice to test their finding: The rodents still went gray. Undaunted, the researchers discovered that animals under stress also release norepinephrine from the sympathetic nervous system. The chemical reaches hair follicles and depletes them of pigment-producing stem cells.

Norepinephrine fast facts

CAS Reg. No.	51-41-2
SciFinder nomenclature	1,2-Benzenediol, 4-[(1R)-2-amino-1-hydroxyethyl]-
Empirical formula	C₈H₁₁NO₃
Molar mass	169.18 g/mol
Appearance	Off-white to tan crystals; colorless microcrystals
Melting point	217 ºC
Water solubility	0.85 g/L

Norepinephrine hazard information

Hazard class：Acute toxicity, oral, category 2
H300—Fatal if swallowed
Hazard class：Acute toxicity, dermal, category 2
H310—Fatal in contact with skin
Hazard class：Acute toxicity, inhalation, category 1
H330—Fatal if inhaled

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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