Alpha-甲基-5-羟色胺马来酸盐 | 304-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: Alpha-甲基-5-羟色胺马来酸盐
• 中文别名: Α-甲基-5-羟色胺马来酸盐
• 英文名称: 3-(2-Amino-propyl)-1H-indol-5-ol
• 英文别名: α-methyl-5-hydroxytryptamine；α-methyl-serotonin；α-methyl 5-HT；3-(2-aminopropyl)-1H-indol-5-ol
• CAS: 304-52-9
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: LYPCGXKCQDYTFV-UHFFFAOYSA-N

物化性质

• 沸点：
  411.7±30.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)
• 溶解度：
  H2O:8 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 安全说明：
  S22,S24/25

反应信息

• 作为反应物：
  描述：

  Alpha-甲基-5-羟色胺马来酸盐 、 alkaline earth salt of/the/ methylsulfuric acid 在 sheep pineal supernatant (serotonin-N-acetyl transferase) 、 优降宁 作用下， 以 phosphate buffer 为溶剂， 反应 0.17h， 生成 N-acetyl-DL-α-methylserotonin
  参考文献：
  名称：

  松果体5-羟基色胺-N-乙酰基转移酶的底物和抑制剂的结构活性关系：初步研究。

  摘要：

  色胺，（1-萘基）乙胺和苯乙胺衍生物作为绵羊松果体5-羟色胺-N-乙酰基转移酶（5-HT-NAT）的底物进行了测试，后者是褪黑素合成的关键酶。几乎所有的吲哚衍生物都具有与色胺类似的亲和力（Km = 0.05 mM），而取代的萘和苯基衍生物的效价较低。但是，Km值似乎受取代基的位阻和极性性质影响。萘和苯基衍生物的Vmax值通常比吲哚衍生物的Vmax值高10-20倍，并且未观察到明确的结构活性关系。褪黑激素和几种生物等位衍生物被证明是5-HT-N-乙酰基转移酶的抑制剂。初步数据表明，在5-50 microM的浓度范围内，褪黑激素是一种竞争性抑制剂（IC50 = 10 microM），对松果体自身的合成具有浓度依赖性的抑制作用。然而，生物等位萘衍生物被表征为混合抑制剂。公认的褪黑素能拮抗剂（1-萘基）乙基乙酰氨基也被证明是5-HT-N-乙酰基转移酶的抑制剂（IC50 = 8 microM），是调

  DOI：

  10.1016/0014-2999(96)00228-2
• 作为产物：
  描述：

  1-(5-(benzyloxy)-1H-indol-3-yl)propan-2-amine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 Alpha-甲基-5-羟色胺马来酸盐
  参考文献：
  名称：

  5-HT1 and 5-HT2 binding profiles of the serotonergic agents .alpha.-methylserotonin and 2-methylserotonin

  摘要：

  alpha-Methyl-5-hydroxytryptamine (alpha-Me-5-HT; 2) and 2-methyl-5-hydroxytryptamine (2-Me-5-HT; 3) are considered to be 5-HT2-selective and 5-HT3-selective agents, respectively. These agents were synthesized and examined at serotonin (5-HT) binding sites because there is relatively little documentation as to their selectivity and because they have not been previously examined at the newly discovered 5-HT1D and 5-HT1E sites. As previously reported, 2-Me-5-HT possesses a low affinity (Ki greater than 500 nM) for 5-HT1A, 5-HT1B, 5-HT1C, and 5-HT2 sites; this agent also displays a low affinity for 5-HT1D (Ki = 1220 nM) and 5-HT1E (Ki greater than 10,000 nM) sites. However, alpha-Me-5-HT displays little selectivity for 5-HT1A, 5-HT1B, 5-HT1C, and 5-HT1D sites (Ki = 42, 85, 150, and 150 nM, respectively) and a very low affinity for 5-HT1E (Ki greater than 10,000 nM) sites. Depending upon the radioligand used to label the sites, alpha-Me-5-HT displays either a low affinity (Ki = 880 nM with [3H]ketanserin) or a high affinity (Ki = 3 nM with [3H]DOB) for 5-HT2 sites. These results suggest that alpha-Me-5-HT is not as selective as previously considered and that caution should be used when employing this agent in pharmacological studies because it may act as mixed 5-HT1/5-HT2 agonist.

  DOI：

  10.1021/jm00164a046

文献信息

• BRADYKININ RECEPTOR AGONISTS AND USES THEREOF TO TREAT OCULAR HYPERTENSION AND GLAUCOMA
  申请人：Combrink Keith D.

  公开号：US20120046285A1

  公开（公告）日：2012-02-23

  The invention provides compositions and methods for treating and/or preventing ocular disorders associated with increased intraocular pressure. In particular, the compounds are bradykinin agonists.

  这项发明提供了用于治疗和/或预防与眼内压增高相关的眼部疾病的组合物和方法。具体来说，这些化合物是激肽酶激动剂。
• HETEROCYCLIC COMPOUNDS, PROCESS FOR PREPARATION OF THE SAME AND USE THEREOF
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：US20170158680A1

  公开（公告）日：2017-06-08

  The present invention provides a heterocyclic compound represented by the formula (I), its stereoisomers, or a pharmaceutically acceptable salt thereof, pharmaceutical compositions thereof, and their use in preparing a medicament for the prevention and/or treatment of central nervous system disease.

  本发明提供了一种由公式（I）表示的杂环化合物，其立体异构体，或其药用可接受的盐，其药物组合物，以及它们用于制备预防或治疗中枢神经系统疾病的药物。
• ARYL AND HETEROARYL TETRAHYDROBENZAZEPINE DERIVATIVES AND THEIR USE FOR TREATING GLAUCOMA
  申请人：Mohapatra Suchismita

  公开号：US20070293475A1

  公开（公告）日：2007-12-20

  Aryl tetrahydrobenzazepine derivatives with minimal 5-HT 2B activity relative to 5-HT 2A and 5-HT 2C activity that are useful for treating glaucoma are disclosed.

  本发明涉及一种对5-HT2A和5-HT2C活性相对较小的芳基四氢苯并哌啶衍生物，用于治疗青光眼。
• [EN] PYRROLOQUINOLINE DERIVATIVES AS 5-HT6 ANTAGONISTS, PREPARATION METHOD AND USE THEREOF<br/>[FR] DÉRIVÉS DE PYRROLOQUINOLINE UTILISÉS COMME ANTAGONISTES DE 5-HT6, LEUR PROCÉDÉ DE PRÉPARATION ET LEUR UTILISATION
  申请人：UNIV JAGIELLOŃSKI

  公开号：WO2015012704A1

  公开（公告）日：2015-01-29

  This invention concerns pyrroloquinoline derivatives as antagonists of 5-HT6 receptors, to methods for the preparation of these compounds and to novel intermediates useful for their synthesis. The invention also relates to the uses of such compounds and compositions, particularly their use in administering them to patients to achieve a therapeutic effect in schizophrenia, anxiety, depression, maniac depression, epilepsy, obsessive compulsive disorders, mood disorders, migraine, Alzheimer's disease, age related cognitive decline, mild cognitive impairment, sleep disorders, eating disorders, anorexia, bulimia, panic attacks, attention deficit hyperactivity disorder, attention deficit disorder, Parkinson's disease, Huntington's disease, withdrawal from abuse of cocaine, ethanol, nicotine or benzodiazepines, pain, obesity and type-2 diabetes, functional bowel disorder, Irritable Bowel Syndrome. The compounds have the general formula (XIV), wherein the symbols have the meanings given in the description.

  这项发明涉及吡咯喹啉衍生物作为5-HT6受体拮抗剂，以及制备这些化合物的方法和用于它们合成的新型中间体。该发明还涉及这些化合物和组合物的用途，特别是它们在向患者施用以达到治疗精神分裂症、焦虑、抑郁症、躁狂抑郁症、癫痫、强迫性障碍、情绪障碍、偏头痛、阿尔茨海默病、年龄相关认知衰退、轻度认知功能障碍、睡眠障碍、进食障碍、厌食症、贪食症、惊恐发作、注意力缺陷多动障碍、注意力缺陷障碍、帕金森病、亨廷顿病、戒除可卡因、乙醇、尼古丁或苯二氮卓类药物滥用、疼痛、肥胖和2型糖尿病、功能性肠道紊乱、肠易激综合征等方面的用途。这些化合物具有一般式（XIV），其中符号的含义如描述中所述。
• [EN] ARYLSULFONYL PYRAZOLINE CARBOXAMIDINE DERIVATIVES AS 5-HT6 ANTAGONISTS<br/>[FR] DÉRIVÉS DE CARBOXAMIDINE DE PYRAZOLINE ARYLSULFONYLIQUE FORMANT DES ANTAGONISTES DE 5-HT6
  申请人：SOLVAY PHARM BV

  公开号：WO2009115515A1

  公开（公告）日：2009-09-24

  This invention concerns arylsulfonyl pyrazoline carboxamidine derivatives as antagonists of 5- HT6 receptors, to methods for the preparation of these compounds and to novel intermediates useful for their synthesis. The invention also relates to the uses of such compounds and compositions, particularly their use in administering them to patients to achieve a therapeutic effect in Parkinson's disease, Huntington's chorea, schizophrenia, anxiety, depression, manic depression, psychoses, epilepsy, obsessive compulsive disorders, mood disorders, migraine, Alzheimer's disease, age related cognitive decline, mild cognitive impairment, sleep disorders, eating disorders, anorexia, bulimia, binge eating disorders, panic attacks, akathisia, attention deficit hyperactivity disorder, attention deficit disorder, withdrawal from abuse of cocaine, ethanol, nicotine or benzodiazepines, pain, disorders associated with spinal trauma or head injury, hydrocephalus, functional bowel disorder, Irritable Bowel Syndrome, obesity and type-2 diabetes. The compounds have the general formula (1) wherein the symbols have the meanings given in the description.

  这项发明涉及芳基磺酰基吡唑啉羧酰胺衍生物作为5-HT6受体拮抗剂，以及用于制备这些化合物的方法和用于它们合成的新型中间体。该发明还涉及这些化合物和组合物的用途，特别是它们在向患者施用以达到在帕金森病、亨廷顿舞蹈症、精神分裂症、焦虑、抑郁症、躁郁症、精神病、癫痫、强迫性障碍、情绪障碍、偏头痛、阿尔茨海默病、与年龄相关的认知下降、轻度认知障碍、睡眠障碍、进食障碍、厌食症、暴食症、暴食症、恐慌发作、不安定症、注意力缺陷多动障碍、注意力缺陷障碍、戒除可卡因、乙醇、尼古丁或苯二氮卓类药物滥用、疼痛、与脊柱损伤或头部损伤相关的障碍、脑积水、功能性肠道障碍、肠易激综合征、肥胖和2型糖尿病中的治疗效果方面的应用。这些化合物具有一般公式（1），其中符号的含义如描述中所示。