Lysergic acid alpha-hydroxyethylamide | 3343-15-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: Lysergic acid alpha-hydroxyethylamide
• 英文别名: (6aR,9R)-N-(1-hydroxyethyl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• CAS: 3343-15-5
• 化学式: C₁₈H₂₁N₃O₂
• 分子量: 311.4
• InChiKey: WYTJZJPVCDWOOI-WPJLSRQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  68.4
• 氢给体数：
  3
• 氢受体数：
  3

ADMET

毒理性

• 毒性总结

麦角生物碱倾向于作为一个整体发挥作用，它们在肾上腺素能、多巴胺能和血清素能受体上产生复杂且多变的部分激动或拮抗作用。与这些效果相关的变量受到药剂、剂量、物种、组织、生理和内分泌状态以及实验条件的影响。特别是，麦角生物碱已被证明对5-HT1和5-HT2血清素受体、D1和D2多巴胺受体以及α-肾上腺素受体具有显著的亲和力。这可能导致多种不同的效果，包括血管收缩、惊厥和幻觉。对LSH的动物研究表明，它具有类似于麦角新碱的催产素和肾上腺素阻滞作用。（A2914, A2915, A2916, A2919）

Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Variables relating to these effects are influenced by the agent, dosage, species, tissue, physiological, and endocrinological state, and experimental conditions. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. Animal studies of LSH have shown it to have oxytocic and adrenergic blocking effects similar to ergometrine. (A2914, A2915, A2916, A2919)

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

摄入麦角生物碱已知会导致麦角中毒。麦角中毒有两种形式，坏疽型和抽搐型，这很可能取决于存在的麦角生物碱的不同种类和数量。

Ingestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (A2913)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服、皮肤、吸入和parenteral（被污染的药物）。

Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

痉挛性麦角中毒可以引起痛苦的抽搐和痉挛、腹泻、感觉异常、瘙痒、头痛、恶心和呕吐。通常胃肠道的反应会先于中枢神经系统的影响。除了抽搐，还可能出现幻觉和包括躁狂或精神病的心理影响。坏疽性麦角中毒由于在血液循环较差的远端结构，如手指和脚趾中引起的血管收缩，从而导致干性坏疽。症状包括脱皮、周围脉搏弱、外周感觉丧失、水肿，最终导致受影响的组织死亡和脱落。

Convulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (L1920)

来源:Toxin and Toxin Target Database (T3DB)

文献信息

• Extracts of Cranberry and Methods of Using Thereof
  申请人：Alberte Randall S.

  公开号：US20100028469A1

  公开（公告）日：2010-02-04

  The present disclosure relates in part to extracts of cranberry ( Vaccinium macrocarpon ) comprising an enriched amount of certain compounds having anti-infective activity, e.g. antibacterial and/or antifungal activity, e.g. activity against C. albicans . Another aspect of the disclosure relates to combined cranberry and cinnamon extracts. In certain embodiments, these combined extracts have been optimized to control urinary tract infections caused by E. coli, S. aureus and C. albicans . Certain embodiments of the extract are enriched in bioactive compounds that have been shown to inhibit C. albicans adhesion and/or biofilm formation and its growth in vitro. In another aspect of the disclosure, the extracts are enriched in bioactives derived from cranberry and cinnamon that have been shown to inhibit the attachment and the growth of common urinary tract pathogens like E. coli, S. aureus and C. albicans.
• US5616493A
  申请人：——

  公开号：US5616493A

  公开（公告）日：1997-04-01