4-(2-氯乙基)-1,2-二甲氧基苯 | 24973-25-9

• 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: 4-(2-氯乙基)-1,2-二甲氧基苯
• 英文名称: (+/-)-1-(2,5-dimethoxyphenyl)-2-aminopropane hydrochloride
• 英文别名: 2-(2,5-dimethoxy-phenyl)-1-methyl-ethylamine; hydrochloride；2-(2,5-Dimethoxy-phenyl)-1-methyl-aethylamin; Hydrochlorid；1-(2,5-dimethoxyphenyl)propan-2-amine hydrochloride；1-(2,5-Dimethoxyphenyl)-2-aminopropan-HCl；1-(2.5-Dimethoxy-phenyl)-2-amino-propan；2,5-dimethoxyamphetamine hydrochloride；1-(2,5-Dimethoxyphenyl)propan-2-amine;hydron;chloride
• CAS: 24973-25-9
• 化学式: C₁₁H₁₇NO₂*ClH
• 分子量: 231.722
• InChiKey: OLBMBFHNGDUGST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  44.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-氯乙基)-1,2-二甲氧基苯 在 盐酸 作用下， 以 甲醇 、 氯苯 为溶剂， 反应 6.5h， 生成 1-[2,5-Dimethoxy-4-(methoxymethyl)phenyl]propan-2-ylazanium;chloride
  参考文献：
  名称：

  DOMC1 和 DOMOM，两种新型 5-HT2A 受体配体的合成和 5-HT2A 放射性配体受体结合分析

  摘要：

  两种新活性物质DOMCl（1-（4-氯甲基-2，5-二甲氧基苯基）-2-丙胺；2）和DOMOM（1-（2，5-二甲氧基-4-甲氧基甲基苯基）-2-丙胺的合成; 3）什么发展。出乎意料的是，Blanc 反应允许成功合成在 4 位具有取代甲基的 2, 5-二甲氧基苯丙胺衍生物，因为在反应过程中发生反应物的溶剂化。然后，在 5-HT2A 放射性配体受体结合试验中检查了它们对 5-HT2A 受体的亲和力。对这些物质的研究非常有趣，因为通过基于 mescalin 单位的初步分子模型研究预测，它们是潜在的新致幻剂，应添加到法律禁止的物质清单中。假设 DOMCl 作为致幻剂的效力比 mescalin 强 82 倍，DOMOM 的效力强 94 倍。5-HT2A 放射性配体受体结合研究表明，DOMC1 和 DOMOM 对 5-HT2A 受体的亲和力低于预期，但分别比美斯卡林高 1.6 和 8.7 倍。因此，可以考虑将这些物质列为潜在的滥用药物。

  DOI：

  10.1002/ardp.200390014
• 作为产物：
  描述：

  N-{2-[2,5-Dimethoxy-4-(piperidin-1-ylazo)-phenyl]-1-methyl-ethyl}-2,2,2-trifluoro-acetamide 在 sodium hydroxide 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 34.5h， 生成 4-(2-氯乙基)-1,2-二甲氧基苯
  参考文献：
  名称：

  [125I] -1-（2,5-二甲氧基-4-碘苯基）-2-氨基丙烷：一种碘标记的放射性配体，专门标记了5-HT2 5-羟色胺受体的激动剂高亲和力状态。

  摘要：

  DOI：

  10.1021/jm00396a003

文献信息

• Dopamine analog amide
  申请人：——

  公开号：US20010056116A1

  公开（公告）日：2001-12-27

  The invention involves the formation of a prodrug from a fatty acid carrier and a neuroactive drug. The prodrug is stable in the environment of both the stomach and the bloodstream and may be delivered by ingestion. The prodrug passes readily through the blood brain barrier. Once in the central nervous system, the prodrug is hydrolyzed into the fatty acid carrier and the drug to release the drug. In a preferred embodiment, the carrier is 4, 7, 10, 13, 16, 19 docosahexa-enoic acid and the drug is dopamine. Both are normal components of the central nervous system. The covalent bond between the drug and the carrier preferably is an amide bond, which bond may survive the conditions in the stomach. Thus, the prodrug may be ingested and will not be hydrolyzed completely into the carrier molecule and drug molecule in the stomach.

  该发明涉及使用脂肪酸载体和神经活性药物形成前药。该前药在胃和血液流动环境中稳定，并可通过口服递送。该前药容易穿过血脑屏障。一旦进入中枢神经系统，前药被水解成脂肪酸载体和药物以释放药物。在首选实施方式中，载体是4,7,10,13,16,19二十二碳六烯酸，药物是多巴胺。两者都是中枢神经系统的正常成分。药物和载体之间的共价键通常是酰胺键，这种键可以在胃的条件下存活。因此，前药可以被摄入，并且不会在胃中完全水解成载体分子和药物分子。
• HETEROARYL COMPOUNDS AND USES THEREOF
  申请人：Singh Juswinder

  公开号：US20100016296A1

  公开（公告）日：2010-01-21

  The present invention provides compounds, pharmaceutically acceptable compositions thereof, and methods of using the same.

  本发明提供了化合物，其药学上可接受的组成物和使用它们的方法。
• COMPOSITIONS AND METHODS FOR TREATING OCULAR PATHOLOGIES
  申请人：The Board of Supervisors of Louisiana State University and Agricultural and Mechanical College

  公开号：EP3618850A1

  公开（公告）日：2020-03-11
• Low Dosage Serotonin 5-HT2A Receptor Agonist To Suppress Inflammation
  申请人：Nichols Charles D.

  公开号：US20100016280A1

  公开（公告）日：2010-01-21

  Activation of 5-HT 2A receptors using agonists at surprisingly low concentrations was shown to potently inhibit TNF-α-induced inflammation in multiple cell types. Significantly, proinflammatory markers were also inhibited by the agonist, (R)-DOI, even many hours after treatment with TNF-α. With the exception of a few natural toxins, no current drugs or small molecule therapeutics demonstrate a comparable potency for any physiological effect. TNF-α and TNF-α receptor mediated inflammatory pathways have been strongly implicated in a number of diseases, including atherosclerosis, asthma, rheumatoid arthritis, psoriasis, type II diabetes, depression, schizophrenia, and Alzheimer's disease. Importantly, because (R)-DOI can significantly inhibit the effects of TNF-α many hours after the administration of TNF-α, potential therapies could be aimed not only at preventing inflammation, but also treating inflammatory injury that has already occurred or is ongoing.
• LOW DOSAGE SEROTONIN 5-HT2A RECEPTOR AGONIST TO SUPPRESS INFLAMMATION
  申请人：NICHOLS Charles D.

  公开号：US20180055791A1

  公开（公告）日：2018-03-01

  Activation of 5-HT 2A receptors using agonists at surprisingly low concentrations was shown to potently inhibit TNF-α-induced inflammation in multiple cell types. Significantly, proinflammatory markers were also inhibited by the agonist, (R)-DOI, even many hours after treatment with TNF-α. With the exception of a few natural toxins, no current drugs or small molecule therapeutics demonstrate a comparable potency for any physiological effect. TNF-α and TNF-α receptor mediated inflammatory pathways have been strongly implicated in a number of diseases, including atherosclerosis, asthma, rheumatoid arthritis, psoriasis, type II diabetes, depression, schizophrenia, and Alzheimer's disease. Importantly, because (R)-DOI can significantly inhibit the effects of TNF-α many hours after the administration of TNF-α, potential therapies could be aimed not only at preventing inflammation, but also treating inflammatory injury that has already occurred or is ongoing.