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环线威 | 26419-73-8

中文名称
环线威
中文别名
——
英文名称
Tirpate
英文别名
[(2,4-dimethyl-1,3-dithiolan-2-yl)methylideneamino] N-methylcarbamate
环线威化学式
CAS
26419-73-8
化学式
C8H14N2O2S2
mdl
——
分子量
234.3
InChiKey
GHFMMRFMDHDOBP-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 密度:
    1.3345 (rough estimate)
  • 物理描述:
    Carbamic acid, methyl-, o-(((2,4-dimethyl-1, 3-dithiolan-2-yl)methylene)amino)- appears as a solid. Used as a nematocide. Manufacture discontinued. (EPA, 1998)
  • 溶解度:
    0.00 M
  • 分解:
    When heated to decomp it emits ... fumes of nitrogen oxides and sulfur oxides.

计算性质

  • 辛醇/水分配系数(LogP):
    1.8
  • 重原子数:
    14
  • 可旋转键数:
    3
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.75
  • 拓扑面积:
    101
  • 氢给体数:
    1
  • 氢受体数:
    5

ADMET

代谢
在溶液培养中,将(14)C标记的腈菌素施用于幼嫩的烟草植物(Nicotiana tobacum)后,最初的代谢物是亚砜。还发现了亚砜腈。通过气相色谱-质谱(GC-MS)进行了鉴定。未鉴定出结合物。其中一些通过磺酸酶或葡萄糖苷酶释放。由磺酸酶释放的一种物质的Rf值与亚砜的Rf值相似。
/Following admin of (14)C-labeled Tirpate to young tobacco plants (Nicotiana tobacum) in hydroponic culture/ the initial metabolite was the sulfoxide. The sulfoxide nitrile was also found. Identification was by GC-MS. The conjugated materials were not identified. Some were released by sulfatase or glucosidase. One material released by sulfatase exhibited an Rf similar to that of the sulfoxide.
来源:Hazardous Substances Data Bank (HSDB)
代谢
甲酰胺通过肝脏酶促水解;降解产物由肾脏和肝脏排出。
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
2,4-二甲基-1,3-二硫代戊烷-2-甲醛O-(甲基氨基甲酰)肟是一种胆碱酯酶或乙酰胆碱酯酶(AChE)抑制剂。氨基甲酸酯通过与酶的活性位点上的羧酰胺化形成与胆碱酯酶的不稳定复合物。这种抑制是可逆的。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眼泪汪汪。头痛、流涎、恶心、呕吐、腹痛和腹泻在高剂量暴露下常常是突出的症状。乙酰胆碱酯酶分解神经递质乙酰胆碱,后者在神经和肌肉接头处释放,以使肌肉或器官放松。乙酰胆碱酯酶抑制的结果是乙酰胆碱积聚并持续作用,使得任何神经冲动持续传递,肌肉收缩不会停止。
2,4-Dimethyl-1,3-dithiolane-2-carboxaldehyde O-(methylcarbamoyl)oxime 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、衰竭和抽搐。肌肉无力可能性增加,如果呼吸肌肉受累,可能导致死亡。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、肌肉跳动和麻痹的症状。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出现毒蕈碱过度刺激时,可能会出现视力障碍、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的干扰(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)
吸收、分配和排泄
遵循管理员指导,对水培培养的年轻烟草植株(Nicotiana tabacum)进行研究时发现,(14)C标记的Tirpate很容易被吸收并在整个地上部分传输,但并未迅速重新输送到新的幼叶中。
/Following admin to young tobacco plants (Nicotiana tobacum) in hydroponic culture/ (14)C-labeled Tirpate was readily taken up and translocated throughout the shoot but was not rapidly retranslocated to new young leaves.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险等级:
    6.1(a)
  • 危险类别:
    6.1(a)

同类化合物

雷尼替丁EP杂质J 苯乙酮乙烷-1,2-二基二硫代缩醛 苯丙酮乙烷-1,2-二基二硫代缩醛 硫代磷酸O,O-二乙基S-[2,2-二(乙硫基)丙基]酯 硫代二碳酸叔丁基乙基酯 硫代二碳酸 1-乙基 3-异丙基酯 甲硫基甲酸叔丁酯 甲氧基甲基硫烷基乙烷 甲氧基二硫代甲酸甲酯 甲氧基(甲基硫烷基)甲烷 甲基二[[(二甲基氨基)硫代甲酰]硫代]乙酸酯 甲基8-氧代-6,10-二硫杂螺[4.5]癸烷-7-羧酸酯 环线威 环己基甲硫基甲基醚 环己基二乙酸二乙酯 双(硫代甲氧基甲基)硫醚 双(亚甲基二硫代)四硫富瓦烯 六氢-2'3A-二甲基螺[1,3-二硫环戊并[4,5-B]呋喃-2,3'(2'H)-呋喃] 亚甲基二(氰基亚胺硫代碳酸甲酯) 亚甲基二(二异丁基二硫代氨基甲酸酯) 二邻茴香醚 二硫氰基甲烷 二硫代丁酸甲酯 二甲硫基甲烷 二甲氧基-[(2-甲基-1,3-氧硫杂环戊烷-2-基)甲硫基]-巯基膦烷 二异丙基黄原酸酯 二(硫代碳酸 O-丁基酯)硫代酸酐 二(二甲基二硫代氨基甲酸)亚甲基酯 二(乙硫基)甲烷 二(乙硫基)乙酸乙酯 二(乙氧基硫代羰基)硫醚 二(2-氨基乙基硫基)甲烷 乙醛,二(甲硫基)- 乙酸甲硫甲酯 乙氧基甲基异硫脲盐酸盐 乙丙二砜 乙丁二砜 丙烷-2、2-二基双(磺胺二基)二乙胺 丙烷-2,2-二基双(硫)基]二乙酸 三硫丙酮 [(异丙氧基硫基甲酰基硫基)硫基甲酰基硫基]硫代甲酸O-异丙基酯 [(N,N-二甲基二硫代氨基甲酰)甲基]甲基氰基亚氨二硫代碳酸酯 [(2-羧基乙氧基)甲基]二甲基-锍溴化物(1:1) S-甲基O-(2-甲基丙基)二硫代碳酸酯 S-烯丙基 O-戊基二硫代碳酸酯 S-(环戊基甲基)O-甲基二硫代碳酸酯 O-烯丙基S-(2-巯基乙基)硫代碳酸酯 O-烯丙基S-(1-癸基)硫代碳酸酯 O-乙基黄原酸乙酯 O-乙基S-(3-氧代丁烷-2-基)二硫代碳酸酯