[1-[2-(4-吗啉基)乙基]-1H-吲哚-3-基]-1-萘基甲酮 | 103610-04-4

• 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: [1-[2-(4-吗啉基)乙基]-1H-吲哚-3-基]-1-萘基甲酮
• 英文名称: [1-[2-(morpholinyl)ethyl]-1H-indol-3-yl]-1-naphthalenyl-methanone
• 英文别名: Win 55225；[1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl]-1-naphthalenylmethanone；1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl-(1-naphthyl)methanone；(1-[2-(4-morpholinyl)ethyl]-3-(1-naphthoyl)-indole)；1-[2-(4-morpholinyl)ethyl]-3-(1-naphthoyl)-indole；1-[2-(4-morpholino)ethyl]-3-(1-naphthoyl)indole；1-(2-(4-Morpholinyl)ethyl)-3-(1-naphthoyl) indole；[1-(2-morpholin-4-ylethyl)indol-3-yl]-naphthalen-1-ylmethanone
• CAS: 103610-04-4
• 化学式: C₂₅H₂₄N₂O₂
• 分子量: 384.478
• InChiKey: SZWYXJHTNGJPKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

毒理性

• 解毒与急救

大多数心理障碍可以通过简单的安慰来处理，可能需要辅助使用劳拉西泮、地西泮或咪达唑仑。窦性心动过速通常不需要治疗，但如果必要，可以使用β-受体阻滞剂进行控制。直立性低血压可以通过低头位和静脉输液来处理。没有特定的解毒剂。/大麻/

Most psychological disturbances may be managed by simple reassurance, possibly with adjunctive use of lorazepam, diazepam, or midazolam. Sinus tachycardia usually does not require treatment but if necessary may be controlled with beta-blockers. Orthostatic hypotension responds to head down position and IV fluids. There is no specific antidote. /Marijuana/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

摄入后进行解毒。院前急救。如果可用，给予活性炭。医院。给予活性炭。如果可以迅速给予活性炭，则不需要进行胃排空。增强消除。由于大麻素分布体积大，这些程序无效。/大麻/

Decontamination after ingestion. Prehospital. Administer activated charcoal if available. Hospital. Administer activated charcoal. Gastric emptying is not necessary if activated charcoal can be given promptly. Enhanced elimination. These procedures are not effective owing to the large volume of distribution of cannabinoids. /Marijuana/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐，让患者向前倾或将其置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗救助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于昏迷、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%的生理盐水（NS）或乳酸林格氏液。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。 /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  [1-[2-(4-吗啉基)乙基]-1H-吲哚-3-基]-1-萘基甲酮 在 硝酸 、 乙酸酐 作用下， 反应 0.5h， 以26%的产率得到1-naphthyl{1-[2-(4-morpholinyl)ethyl]-6-nitro-1H-indol-3-yl}methanone
  参考文献：
  名称：

  (Aminoalkyl)indole Isothiocyanates as Potential Electrophilic Affinity Ligands for the Brain Cannabinoid Receptor

  摘要：

  A series of (aminoalkyl)indole compounds, naphthalene analogs of pravadoline (1), has been shown to exhibit cannabinoid agonist activities such as antinociception in animals, inhibition of adenylate cyclase in brain membranes, and binding to the cannabinoid receptor. These pravadoline analogs were selected for the preparation of potential electrophilic affinity ligands based on the synthesis of isothiocyanate derivatives. One isothiocyanatonaphthalene derivative (8) displaced [H-3]CP-55940 binding to a rat brain P2 membrane preparation with an IC50 of 690 nM, which was 10-fold less potent than the parent molecule (IC50 = 73 nM). Isothiocyanate substitution at various positions on the naphthalene moiety of the desmethyl analog 10 gave compounds that displaced [H-3]CP-55940 with IC50 values between 400 and 1000 nM, compared with 46 nM for the parent compound 10. However, 6-isothiocyanato substitution on the indole ring of the desmethyl analog provided isothiocyanate 12 that displaced [H-3]CP-55940 binding with an IC50 of 160 nM. After pretreatment of brain membranes with this high-affinity isothiocyanato ligand followed by washing out the ligand, the membranes were depleted of 90% of the cannabinoid receptor binding capacity. Loss of receptor binding capacity was half-maximal at 300 nM of the derivative under standard assay conditions. As a control, pretreatment with the parent compound at concentrations that were 20 times the K-d failed to alter subsequent binding activity. This study demonstrates that an isothiocyanato (aminoalkyl)-indole (12) can behave as an affinity ligand which binds irreversibly to the cannabinoid receptor in brain and which precludes subsequent binding of the cannabinoid ligand [H-3]CP-55940.

  DOI：

  10.1021/jm950932r
• 作为产物：
  描述：

  3-碘吲哚 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 [1-[2-(4-吗啉基)乙基]-1H-吲哚-3-基]-1-萘基甲酮
  参考文献：
  名称：

  5-Bromo-norborn-2-en-7-one 衍生物作为钯催化羰基化反应的一氧化碳源†

  摘要：

  由 2,5-二甲基-3,4-二苯基环戊二烯酮二聚体 ( 3 ) 与溴马来酸酐 ( 4b ) 反应获得的降冰片烯酮 ( 5b )为钯催化的羰基化反应提供了极好的碱触发一氧化碳源。在两室反应容器中进行的芳基碘化物的氨基羰基化、酮酰胺合成和 Suzuki-Miyaura 反应产生了良好的羰基化产物产率。

  DOI：

  10.1039/c9ra06594f

文献信息

• Detection of Synthetic Cannabinoids
  申请人：Benchikh Elouard

  公开号：US20120208213A1

  公开（公告）日：2012-08-16

  The invention describes methods and kits for detecting and determining current and future synthetic cannabinoids from the JWH and CP families. Unique antibodies derived from novel immunogens enable said methods and kits.

  这项发明描述了检测和确定JWH和CP家族当前和未来合成大麻素的方法和试剂盒。源自新型免疫原的独特抗体使这些方法和试剂盒得以实现。
• Detection of synthetic cannabinoids
  申请人：Randox Laboratories Ltd.

  公开号：EP2698385A1

  公开（公告）日：2014-02-19

  The invention describes methods and kits for detecting and determining current and future synthetic cannabinoids from the JWH and CP families. Unique antibodies derived from immunogens enable said methods and kits.

  这项发明描述了检测和确定JWH和CP家族当前和未来合成大麻素的方法和试剂盒。从免疫原获得的独特抗体使这些方法和试剂盒成为可能。
• DETECTION OF SYNTHETIC CANNABINOIDS
  申请人：RANDOX LABORATORIES LIMITED

  公开号：US20150118763A1

  公开（公告）日：2015-04-30

  The invention describes methods and kits for detecting and determining current and future synthetic cannabinoids from the JWH and CP families. Unique antibodies derived from novel immunogens enable said methods and kits.

  这项发明描述了用于检测和确定当前和未来JWH和CP家族合成大麻素的方法和试剂盒。从新型免疫原中获得的独特抗体使这些方法和试剂盒得以实现。
• COMPOSITION AND METHODS FOR TREATING GLIOBLASTOMA
  申请人：Stella Nephi

  公开号：US20130197026A1

  公开（公告）日：2013-08-01

  The disclosure provides methods of treating glioblastoma, methods of screening for compounds that treat glioblastoma, and pharmaceutical compositions useful the treatment of glioblastoma.

  该披露提供了治疗胶质母细胞瘤的方法，筛选治疗胶质母细胞瘤的化合物的方法，以及用于治疗胶质母细胞瘤的药物组合物。
• PERIPHERALLY-ACTING CANNABINOID RECEPTOR AGONISTS FOR CHRONIC PAIN
  申请人：The Regents of the University of California

  公开号：US20150239859A1

  公开（公告）日：2015-08-27

  Peripherally acting cannabinoid agonist compounds, pharmaceutical compositions, and methods of using them are presented.

  本文介绍了外周作用的大麻素激动剂化合物、制药组合物以及使用它们的方法。