N-异丙基-5-甲氧基色氨酸 | 109921-55-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 色氨酸类衍生物
• 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: N-异丙基-5-甲氧基色氨酸
• 英文名称: 5-Methoxy-N-isopropyltryptamine
• 英文别名: 5-MeO-IPT；isopropyl-[2-(5-methoxy-indol-3-yl)-ethyl]-amine；Isopropyl-<2-(5-methoxy-indol-3-yl)-ethyl>-amin；N-[2-(5-methoxy-1H-indol-3-yl)ethyl]propan-2-amine
• CAS: 109921-55-3
• 化学式: C₁₄H₂₀N₂O
• mdl: MFCD03763634
• 分子量: 232.326
• InChiKey: QQZJNZJNPDORBO-UHFFFAOYSA-N

物化性质

• 沸点：
  391.5±27.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  2

ADMET

代谢

5-MeO-IPT是人类已知的一种代谢物，它是5-甲氧基-N,N-二异丙基色胺的代谢产物。

5-MeO-IPT is a known human metabolite of 5-Methoxy-N,N-diisopropyltryptamine.

来源:NORMAN Suspect List Exchange

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  N-异丙基-5-甲氧基色氨酸 、 乙醛酸 以 水 为溶剂， 生成 2-isopropyl-6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylic acid
  参考文献：
  名称：

  Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  A structure-activity relationship study was conducted on a series of tetrahydro-beta-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNF alpha production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity. (c) 2007 Elsevier Ltd. All rialuts reserved.

  DOI：

  10.1016/j.bmcl.2007.05.070
• 作为产物：
  描述：

  N-[2-(5-methoxy-1H-indol-3-yl)ethyl]propan-2-imine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 N-异丙基-5-甲氧基色氨酸
  参考文献：
  名称：

  Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  A structure-activity relationship study was conducted on a series of tetrahydro-beta-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNF alpha production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity. (c) 2007 Elsevier Ltd. All rialuts reserved.

  DOI：

  10.1016/j.bmcl.2007.05.070

文献信息

• Oxidative metabolism of 5-methoxy-N,N-diisopropyltryptamine (Foxy) by human liver microsomes and recombinant cytochrome P450 enzymes
  作者：Shizuo Narimatsu、Rei Yonemoto、Keita Saito、Kazuo Takaya、Takuya Kumamoto、Tsutomu Ishikawa、Masato Asanuma、Masahiko Funada、Kimio Kiryu、Shinsaku Naito、Yuzo Yoshida、Shigeo Yamamoto、Nobumitsu Hanioka

  DOI：10.1016/j.bcp.2006.01.015

  日期：2006.4

  vitro quantitative studies of the oxidative metabolism of (5-methoxy-N,N-diisopropyltryptamine, 5-MeO-DIPT, Foxy) were performed using human liver microsomal fractions and recombinant CYP enzymes and synthetic 5-MeO-DIPT metabolites. 5-MeO-DIPT was mainly oxidized to O-demethylated (5-OH-DIPT) and N-deisopropylated (5-MeO-IPT) metabolites in pooled human liver microsomes. In kinetic studies, 5-MeO-DIPT

  使用人肝微粒体组分，重组CYP酶和合成的5-MeO-DIPT代谢物进行了（5-甲氧基-N，N-二异丙基色胺，5-MeO-DIPT，Foxy）氧化代谢的体外定量研究。5-MeO-DIPT在合并的人肝微粒体中主要被氧化为O-去甲基化（5-OH-DIPT）和N-去异丙基化（5-MeO-IPT）代谢产物。在动力学研究中，5-MeO-DIPT O-去甲基化显示单相动力学，而其N-去异丙基显示三相动力学。在酵母或昆虫细胞中表达的六种重组CYP酶（CYP1A2，CYP2C8，CYP2C9，CYP2C19，CYP2D6和CYP3A4）中，只有CYP2D6具有5-MeO-DIPT O-脱甲基酶活性，而CYP1A2，CYP2C4，CYP2C4，CYP2C4，CYP1A2，CYP1A2，CYP2C4，CYP2C4，CYP2C8 -MeO-DIPT N-去异丙基酶活性。CYP2D6的表观Km值接近于5-MeO-DIPT
• Dihydropyrancarboxamides and uses thereof
  申请人：Schreiber L. Stuart

  公开号：US20080070916A1

  公开（公告）日：2008-03-20

  The present invention provides novel dihydropyrancarboxamide compounds of formula (I): and collections of these compounds, and provides methods for the synthesis of these compounds; wherein R 1 -R 6 are as defined herein. Additionally, the present invention provides pharmaceutical compositions and methods for treating disorders such as proliferative diseases, and cancer, to name a few.

  本发明提供了式（I）的新型二氢吡嗪羧酰胺化合物以及这些化合物的集合，并提供了合成这些化合物的方法；其中R1-R6如本文所定义。此外，本发明还提供了治疗增生性疾病和癌症等疾病的药物组合物和方法。
• Oxidation of 5-methoxy-N,N-diisopropyltryptamine in rat liver microsomes and recombinant cytochrome P450 enzymes
  作者：Shizuo Narimatsu、Rei Yonemoto、Kazufumi Masuda、Takashi Katsu、Masato Asanuma、Tooru Kamata、Munehiro Katagi、Hitoshi Tsuchihashi、Takuya Kumamoto、Tsutomu Ishikawa、Shinsaku Naito、Shigeru Yamano、Nobumitsu Hanioka

  DOI：10.1016/j.bcp.2007.09.019

  日期：2008.2

  The oxidative metabolism of 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT), a tryptamine-type designer drug, was studied using rat liver microsomal fractions and recombinant cytochrome P450 (CYP) enzymes. 5-MeO-DIPT was biotransformed mainly into a side-chain N-deisopropylated metabolite and partially into an aromatic ring O-demethylated metabolite in liver microsomal fractions from untreated rats of both sexes. This metabolic profile is different from our previous findings in human liver microsomal fractions, in which the aromatic ring O-demethylation was the major pathway whereas the side-chain N-deisopropylation was minor [Narimatsu S, Yonemoto R, Saito K, Takaya K, Kumamoto T, Ishikawa T, et al. oxidative metabolism of 5-methoxy-N,N-diisopropyltryptamine (Foxy) by human liver microsomes and recombinant cytochrome P450 enzymes. Biochem Pharmacol 2006;71:1377-85]. Kinetic and inhibition studies indicated that the side-chain N-dealkylation is mediated by CYP2C11 and CYP3A2, whereas the aromatic ring O-demethylation is mediated by CYP2D2 and CYP2C6 in untreated male rats. Pretreatment of male rats with p-naphthoflavone (BNF) produced an aromatic ring 6-hydroxylated metabolite. Recombinant rat and human CYP1A1 efficiently catalyzed 5-MeO-DIPT 6-hydroxylation under the conditions used. These results provide valuable information on the metabolic fate of 5-MeO-DIPT in rats that can be used in the toxicological study of this designer drug. (c) 2007 Elsevier Inc. All rights reserved.
• US7186709B2
  申请人：——

  公开号：US7186709B2

  公开（公告）日：2007-03-06
• [EN] ASYMMETRIC ALLYL TRYPTAMINES<br/>[FR] ALLYL TRYPTAMINES ASYMÉTRIQUES
  申请人：[en]ALEXANDER SHULGIN RESEARCH INSTITUTE

  公开号：WO2023034645A2

  公开（公告）日：2023-03-09

  Provided are allyl tryptamines, such as asymmetric allyl tryptamines. In some embodiments, such compounds modulate the activity of monoamine receptors and/or monoamine transporters. Also provided are methods for the preparation of allyl tryptamines and pharmaceutical compositions thereof. Methods of using the allyl tryptamines, alone or in combination with other therapeutic agents, are provided. In some embodiments, allyl tryptamines are used to treat CNS disorders, such as mental health conditions and neurodegenerative disorders, or are used for the improvement of mental health or functioning.