(2-羟基苯基)N-甲基氨基甲酸酯 | 10309-97-4

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2-羟基苯基)N-甲基氨基甲酸酯
• 英文名称: pyrocatechol monomethylcarbamate
• 英文别名: pyrocatechol methylcarbamate；N-methyl-carbamic acid 2-hydroxy-phenyl ester；o-hydroxyphenyl methylcarbamate；pyrocatechol mono-N-methylcarbamate；pyrocatecholmono-N-methyl carbamate；N-Methyl-carbamidsaeure-(2-hydroxyphenyl)-ester；(2-hydroxyphenyl) N-methylcarbamate
• CAS: 10309-97-4
• 化学式: C₈H₉NO₃
• mdl: MFCD00128540
• 分子量: 167.164
• InChiKey: CEHPRGMPLPBMLL-UHFFFAOYSA-N

物化性质

• 熔点：
  126-127.5 °C
• 沸点：
  295.73°C (rough estimate)
• 密度：
  1.2917 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

甲酰胺通过肝脏酶促水解；降解产物通过肾脏和肝脏排出。

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

2-羟基苯基甲基氨基甲酸盐是一种胆碱酯酶或乙酰胆碱酯酶（AChE）抑制剂。氨基甲酸盐通过与胆碱酯酶活性位点上的羧化作用形成不稳定的复合物。这种抑制作用是可逆的。胆碱酯酶抑制剂抑制乙酰胆碱酯酶的作用。由于其基本功能，干扰乙酰胆碱酯酶作用的化学物质是强效的神经毒素，即使在低剂量下也会导致过度流涎和流泪。在更高水平的暴露下，头痛、流涎、恶心、呕吐、腹痛和腹泻常常是显著的。乙酰胆碱酯酶分解神经递质乙酰胆碱，该递质在神经和肌肉接点处释放，以便让肌肉或器官放松。乙酰胆碱酯酶抑制的结果是乙酰胆碱积聚并继续发挥作用，使得任何神经冲动持续传递，肌肉收缩不会停止。

2-Hydroxyphenyl methylcarbamate is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

急性暴露于胆碱酯酶抑制剂可能会导致胆碱能危象，表现为严重的恶心/呕吐、流涎、出汗、心动过缓、低血压、崩溃和抽搐。肌肉无力可能性增加，如果呼吸肌肉受累，可能会导致死亡。在运动神经积累的乙酰胆碱会导致神经肌肉接头处烟碱表达的过度刺激。当这种情况发生时，可以看到肌肉无力、疲劳、肌肉痉挛、肌肉颤动和麻痹的症状。当自主神经节积累乙酰胆碱时，这会导致交感系统中烟碱表达的过度刺激。与此相关的症状是高血压和低血糖。由于乙酰胆碱积累，中枢神经系统中烟碱乙酰胆碱受体的过度刺激会导致焦虑、头痛、抽搐、共济失调、呼吸和循环抑制、震颤、全身无力，甚至可能昏迷。当由于副交感神经乙酰胆碱受体处乙酰胆碱过多而导致副交感神经过度刺激时，会出现视力障碍、胸部紧绷、由于支气管收缩引起的喘息、支气管分泌物增加、唾液分泌增加、流泪、出汗、肠蠕动和排尿的症状。长期高（>10年）暴露会导致神经心理学后果，包括感知和视觉运动处理方面的障碍（A15321）。

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

吸入（L793）；口服（L793）；皮肤给药（L793）

Inhalation (L793) ; oral (L793); dermal (L793)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

与有机磷化合物一样，症状和体征基于过度的胆碱能刺激。与有机磷中毒不同，氨基甲酸酯中毒的持续时间往往较短，因为神经组织乙酰胆碱酯酶的抑制作用是可逆的，且氨基甲酸酯的代谢速度更快。肌肉无力、眩晕、出汗和轻微的身体不适是常见的早期症状。头痛、流涎、恶心、呕吐、腹痛和腹泻在较高暴露水平时常常更为明显。瞳孔收缩伴视力模糊、不协调、肌肉抽搐和言语不清也有报道。(L795)

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (2-羟基苯基)N-甲基氨基甲酸酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 1-氨基-3-甲基尿素
  参考文献：
  名称：

  Ohme,R.; Preuschhof,H., Journal fur praktische Chemie (Leipzig 1954), 1971, vol. 313, p. 626 - 635

  摘要：

  DOI：
• 作为产物：
  描述：

  pyrocatechol carbonate 在 盐酸 、 三乙胺 、 甲胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2-羟基苯基)N-甲基氨基甲酸酯
  参考文献：
  名称：

  Preparation of pyrocatechol methylcarbamate

  摘要：

  Pyrocatechol methylcarbamate是通过在三级胺和最好是溶剂的存在下，将Pyrocatechol carbonate与甲基胺反应制备而成。

  公开号：

  US04537986A1

文献信息

• Pyrocatechol ethers
  申请人：BASF Aktiengesellschaft

  公开号：US04140725A1

  公开（公告）日：1979-02-20

  Compounds of the formula: ##STR1## are disclosed which compound are used to prepare carbamates which are stated to have utility as plant protecting agents and insecticides.

  公式为：##STR1## 的化合物被披露，这些化合物被用来制备氨基甲酸酯，据称这些氨基甲酸酯具有作为植物保护剂和杀虫剂的效用。
• INSECTICIDAL CARBAMATES EXHIBITING SPECIES-SELECTIVE INHIBITION OF ACETYLCHOLINESTERASE (AChE)
  申请人：Carlier Paul

  公开号：US20090068242A1

  公开（公告）日：2009-03-12

  The present invention includes insecticidal carbamates that are useful, for example, for the control of insects, such as mosquitoes, which can be used in applications where exposure to and/or contact with humans is likely. The insecticides of the present invention include phenyl N-methyl carbamates and compositions comprising them that exhibit species-selective inhibition of acetylcholinesterase (AChE) and are preferably toxic to mosquitoes but not humans. Of particular interest are compounds of Formula (I) and Formula (II): Compounds of Formula (I) and Formula (II) are especially suitable for insecticide treated nets and indoor residual spraying for mosquito control.

  本发明包括杀虫卡巴胺，例如，用于控制昆虫，如蚊子，可用于在可能接触到人类的应用中。本发明的杀虫剂包括苯基N-甲基卡巴胺和包含它们的组合物，这些组合物表现出对乙酰胆碱酯酶（AChE）的物种选择性抑制，并且最好对蚊子有毒而对人类无毒。特别感兴趣的是Formula（I）和Formula（II）的化合物：Formula（I）和Formula（II）的化合物特别适用于杀虫剂处理的蚊帐和室内残留喷雾用于蚊子控制。
• Preparation of o-(1-methoxy-2-chloro)-ethoxyphenyl N-methylcarbamate
  申请人：BASF Aktiengesellschaft

  公开号：US04788324A1

  公开（公告）日：1988-11-29

  O-(1-Methoxy-2-chloro)ethoxyphenyl N-methylcarbamate is prepared by reacting pyrocatechol carbonate with methylamine and then reacting the resulting pyrocatechol monomethylcarbamate with 1,2-dichloroethyl methyl ether in the presence of a secondary amine.

  O-（1-甲氧基-2-氯）乙氧基苯基N-甲基氨基甲酸酯是通过将邻苯二酚碳酸酯与甲胺反应，然后在次生胺的存在下将产生的邻苯二酚单甲基氨基甲酸酯与1,2-二氯乙基甲醚反应制备而成。
• SEPPELT, WOLFGANG;SPROESSER, LINNARD;KERSTEN, SIEGFRIED;HOFMEISTER, PETER+
  作者：SEPPELT, WOLFGANG、SPROESSER, LINNARD、KERSTEN, SIEGFRIED、HOFMEISTER, PETER+

  DOI：——

  日期：——
• REISSENWEBER, G.;KERSTEN, S.;JACOBS, P.;DITTER, W.
  作者：REISSENWEBER, G.、KERSTEN, S.、JACOBS, P.、DITTER, W.

  DOI：——

  日期：——