结晶紫阳离子 | 14426-25-6

• 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: 结晶紫阳离子
• 英文名称: {4-[Bis-(4-dimethylamino-phenyl)-methylene]-cyclohexa-2,5-dienylidene}-dimethyl-ammonium
• 英文别名: gentian violet；crystal violet；methyl violet；Kristallviolett, Kation；Gentian violet cation；[4-[bis[4-(dimethylamino)phenyl]methylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium
• CAS: 14426-25-6；7438-46-2
• 化学式: C₂₅H₃₀N₃
• 分子量: 372.533
• InChiKey: LGLFFNDHMLKUMI-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  215 °C
• 溶解度：
  4 mg/mL
• 碰撞截面：
  207.3 Ų [M+H]+

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  9.5
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

主要发生在肝脏，主要是去甲基化

Primarily hepatic, mostly demethylation

来源:DrugBank

代谢

主要发生在肝脏，主要是去甲基化

Primarily hepatic, mostly demethylation

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

紫花地丁是一种胆碱酯酶或乙酰胆碱酯酶（AChE）抑制剂。胆碱酯酶抑制剂（或“抗胆碱酯酶”）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大的神经毒素，低剂量时会导致过度流涎和眼泪，随后是肌肉痉挛，最终导致死亡。神经气体和许多用于杀虫剂的物质已被证明通过结合乙酰胆碱酯酶活性位点的丝氨酸，完全抑制该酶。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继续发挥作用，使得任何神经冲动不断传递，肌肉收缩不会停止。最常见的乙酰胆碱酯酶抑制剂之一是基于磷的化合物，它们被设计用来结合到酶的活性位点上。结构要求是一个带有两个亲脂性基团的磷原子，一个离去基团（如卤素或硫氰酸盐）以及一个终端氧。

Gentian Violet is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. 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. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

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

急性接触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，如果呼吸肌受到影响，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尼古丁受体的过度刺激。当这种情况发生时，可以看到肌肉无力、疲劳、肌肉痉挛、肌束震颤和麻痹的症状。当自主神经节积累乙酰胆碱时，这会导致交感系统中尼古丁受体的过度刺激。与此相关的症状包括高血压和低血糖。由于乙酰胆碱积累，中枢神经系统中尼古丁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。当由于乙酰胆碱过量而在毒蕈碱乙酰胆碱受体上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。对于男性和女性，在生育、生长和发育方面，某些生殖效应已被特别与有机磷农药暴露联系起来。关于生殖效应的大部分研究都是在农村地区使用农药和杀虫剂的农民中进行的。在女性中，月经周期紊乱、怀孕时间延长、自然流产、死产以及后代的一些发育效应已被与有机磷农药暴露联系起来。产前暴露与胎儿生长和发育受损有关。神经毒性效应也已被与有机磷农药中毒联系起来，在人类中导致四种神经毒性效应：胆碱能综合征、中间综合征、有机磷诱导的迟发性多发性神经病(OPIDP)和慢性有机磷诱导的神经精神障碍(COPIND)。这些综合征在急性接触和慢性接触有机磷农药后出现。

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. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

低剂量暴露的症状包括过度流涎和眼泪。急性剂量症状包括严重的恶心/呕吐、流涎、出汗、心动过缓、低血压、昏厥和抽搐。肌肉无力可能会逐渐加重，如果呼吸肌肉受影响，可能会导致死亡。还可能出现高血压、低血糖、焦虑、头痛、颤抖和共济失调。

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include 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. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性数据

LD50=420 mg/kg (大鼠，口服)。

LD₅₀=420 mg/kg (rat, oral).

来源:Toxin and Toxin Target Database (T3DB)

反应信息

• 作为反应物：
  描述：

  结晶紫阳离子 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 、 异丙醇 为溶剂， 生成 溶剂紫9
  参考文献：
  名称：

  某些三苯甲烷染料的褪色动力学：二甲基亚砜和2-丙醇的电荷，取代基和水性二元混合物的影响

  摘要：

  获得了包括甲基绿（ME 2+），亮绿色（BG +），品红酸（FA 2−）和溴酚蓝（BPB 2-）在内的许多三苯甲烷（TPM）染料的碱性褪色速率常数。2-丙醇（质子溶剂）和二甲基亚砜（DMSO）（非质子溶剂）在不同温度下的二元水性混合物。观察到BG +和ME 2+的反应速率常数增加，FA 2−和BPB 2−的反应速率常数增加随着2-丙醇水溶液和DMSO二元混合物重量百分比的增加而降低。2-丙醇和DMSO除与TPM染料发生疏水相互作用外，还分别通过氢键和离子-偶极相互作用与所用的TPM分子相互作用。通过SESMORTAC模型获得了这些溶液中褪色反应的基本速率常数。此外，研究了许多TPM染料的电荷和取代基对其碱性褪色速率的影响。

  DOI：

  10.1002/kin.20831
• 作为产物：
  描述：

  结晶紫 在 盐酸 、 碘 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.17h， 生成 结晶紫阳离子
  参考文献：
  名称：

  Sensitive spectrophotometric method for determination of some phenothiazine drugs

  摘要：

  针对某些吩噻嗪衍生物开发了一种简单灵敏的分光光度法。该方法是将吩噻嗪衍生物盐酸异丙嗪、盐酸氯丙嗪、盐酸三氟丙嗪、丙氯哒嗪和三氟拉嗪与碘酸钾反应，然后将生成的碘与亮晶紫 (LCV) 反应，在 598 nm 波长处测定氧化 LCV 的颜色。该方法的线性范围分别为 0.05-4.0、0.02-2.0、0.05-5.0、0.1-8.0 和 0.05-2.0 µg mL-1 。对最佳条件和其他分析参数进行了评估。所提出的方法已成功地应用于纯品及其剂型中吩噻嗪衍生物的分析，且未观察到药物制剂中常见辅料的干扰。

  DOI：

  10.1007/s11164-014-1838-8

文献信息

• HAIR COLORING COMPOSITIONS
  申请人：——

  公开号：US20020032933A1

  公开（公告）日：2002-03-21

  A hair coloring composition comprising: (a) from about 0.0003 moles (per 100 g of composition) to less than about 0.09 moles (per 100 g of composition) of an inorganic peroxygen oxidizing agent; and (b) an oxidative hair coloring agent; wherein the pH of each of (a) and (b) is in the range of from about 1 to about 6 and wherein the combined mixture of (a) and (b) has a pH in the range of from about 1 to about 6. The products can provide excellent hair coloring and in-use efficacy benefits including excellent initial color and good wash fastness in combination with reduced hair damage at low pH.

  一种染发组合物，包括：(a)约0.0003摩尔（每100克组合物）至约0.09摩尔（每100克组合物）的无机过氧化氧化剂；和(b)氧化性染发剂；其中(a)和(b)的pH值在约1至约6的范围内，且(a)和(b)的混合物的pH值在约1至约6的范围内。该产品可以提供出色的染发效果和使用效果，包括出色的初始颜色和良好的耐洗性，同时在低pH值下减少头发损伤。
• Hair colouring and conditioning compositions
  申请人：The Procter & Gamble Company

  公开号：US20030113286A1

  公开（公告）日：2003-06-19

  A hair colouring and conditioning composition comprising: (a) a hair colouring agent; and (b) a hair conditioning agent; wherein the composition provides an Average Combing Index Value of greater than 1.2 as measured by the Combing Technical Test Method. The products can provide excellent hair colouring together with excellent conditioning, reduced hair damage, brittleness and dryness, and is convenient and easy to use.

  一种包括： (a) 染发剂；和 (b) 护发剂； 的染发和护理组合物； 其中该组合物通过梳理技术测试方法测得的平均梳理指数值大于1.2。 该产品可以提供优秀的染发效果以及优秀的护理效果，减少头发损伤、脆弱和干燥，且使用方便。
• Hair conditioning compositions and their use in hair colouring compositions
  申请人：The Procter & Gamble Company

  公开号：US20030219399A1

  公开（公告）日：2003-11-27

  The present invention relates to a hair care composition comprising a aminofunctional polysiloxane having a specified average effective particle size which provides improved durable conditioning particularly when utilised in conjunction with a hair colouring composition.

  本发明涉及一种头发护理组合物，包括具有特定平均有效粒径的氨基官能聚硅氧烷，当与染发组合物一起使用时，能提供改善的持久调理效果。
• Enhancement of rates of reaction using neutral water/organic microemulsions as solvent media
  作者：Michael J. Blandamer、John Burgess、Barbara Clark

  DOI：10.1039/c39830000659

  日期：——

  Relative to the rate constants for reactions in aqueous solutions the rate constants for reactions involving (i) Fe(phen)32+(phen = 1,10-phenanthroline), (ii) Fe(5-NO2phen)32+, (iii) 2,4-dinitrochlorobenzene, and (iv) crystal violet with either hydroxide or cyanide ions are increased markedly when two water/organic microemulsions formed from liquid components are used as reaction media; a similar though

  相对于水溶液中反应的速率常数，涉及（i）Fe（phen）3 2+（phen = 1,10-菲咯啉），（ii）Fe（5-NO 2 phen）3 2+的反应速率常数；（iii）当使用由液体组分形成的两种水/有机微乳液作为反应介质时，具有氢氧根或氰化物离子的2,4-二硝基氯苯和（iv）结晶紫显着增加；在相关的水合速率（水解）中观察到了相似但不太明显的变化。
• COLORING AGENTS AND METHODS OF USE THEREOF
  申请人：Living Proof, Inc.

  公开号：US20160106648A1

  公开（公告）日：2016-04-21

  Dyes, compositions comprising dyes and methods for using the same are provided.

  染料、包含染料的组合物以及使用这些染料的方法。

表征谱图