5-Hydroxy-N,N-diisopropyltryptamine | 36288-76-3

• 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
• 英文名称: 5-Hydroxy-N,N-diisopropyltryptamine
• 英文别名: 3-[2-[di(propan-2-yl)amino]ethyl]-1H-indol-5-ol
• CAS: 36288-76-3
• 化学式: C₁₆H₂₄N₂O
• 分子量: 260.379
• InChiKey: HWOLNTJLIUHEOG-UHFFFAOYSA-N

物化性质

• 沸点：
  424.9±35.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

ADMET

代谢

5-羟基-DIPT是5-甲氧基-N,N-二异丙基色胺的人类已知代谢物。

5-hydroxy-DIPT is a known human metabolite of 5-Methoxy-N,N-diisopropyltryptamine.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  5-Hydroxy-N,N-diisopropyltryptamine 、 S-(5’-腺苷基)-L-氯化蛋氨酸 在 1,4-dithio-D,L-threitol 、 HEPES 、 sodium chloride 、 magnesium chloride 作用下， 以 水 为溶剂， 反应 6.0h， 生成 5-甲氧基-N,N-二异丙基色胺
  参考文献：
  名称：

  [EN] MODIFIED INDOLE ALKALOIDS FOR THERAPEUTIC USES
  [FR] ALCALOÏDES INDOLIQUES MODIFIÉS POUR UTILISATIONS THÉRAPEUTIQUES

  摘要：

  本文披露了制备改性吲哚生物碱的酶和改性宿主细胞方法。本文还披露了改性吲哚生物碱及其治疗用于治疗疾病和疾病的方法。

  公开号：

  WO2022133314A1
• 作为产物：
  描述：

  5-Benzyloxy-3-indol-glyoxylylchlorid 在 甲醇 、 palladium on activated charcoal 作用下， 生成 5-Hydroxy-N,N-diisopropyltryptamine
  参考文献：
  名称：

  Barlow; Khan, British Journal of Pharmacology and Chemotherapy, 1959, vol. 14, p. 265,266

  摘要：

  DOI：

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
• Processes for the production of tryptamines
  申请人：New Atlas Biotechnologies LLC

  公开号：US11136293B2

  公开（公告）日：2021-10-05

  Disclosed herein are prokaryotic and eukaryotic microbes, including E. coli and S. cerevisiae, genetically altered to biosynthesize tryptamine and tryptamine derivatives. The microbes of the disclosure may be engineered to contain plasmids and stable gene integrations containing sufficient genetic information for conversion of an anthranilate or an indole to a tryptamine. The fermentative production of substituted tryptamines in a whole-cell biocatalyst may be useful for cost effective production of these compounds for therapeutic use.

  本文公开了经基因改造可生物合成色胺和色胺衍生物的原核和真核微生物，包括大肠杆菌和酿酒葡萄球菌。本发明公开的微生物可被设计成含有质粒和稳定的基因整合，其中包含将蒽酸或吲哚转化为色胺的足够遗传信息。在全细胞生物催化剂中发酵生产取代的色胺可能有助于以具有成本效益的方式生产这些用于治疗的化合物。
• 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.
• PROCESSES FOR THE PRODUCTION OF TRYPTAMINES
  申请人：New Atlas Biotechnologies LLC

  公开号：US20210108238A1

  公开（公告）日：2021-04-15

  Disclosed herein are prokaryotic and eukaryotic microbes, including E. coli and S. cerevisiae , genetically altered to biosynthesize tryptamine and tryptamine derivatives. The microbes of the disclosure may be engineered to contain plasmids and stable gene integrations containing sufficient genetic information for conversion of an anthranilate or an indole to a tryptamine. The fermentative production of substituted tryptamines in a whole-cell biocatalyst may be useful for cost effective production of these compounds for therapeutic use.
• TRYPTAMINE COMPOSITIONS FOR ENHANCING NEURITE OUTGROWTH
  申请人：STAMETS Paul Edward

  公开号：US20210069170A1

  公开（公告）日：2021-03-11

  Described herein are neurotrophic and nootropic compositions and methods for treating subjects with such compositions. In one aspect the composition comprises one or more tryptamines or in pure form or extracts from psilocybin containing mushrooms, or combinations thereof optionally combined with one or more phenethylamines or amphetamines in pure form or extracts from a plant or mushroom, or combinations thereof, optionally one or more erinacines or hericenones in pure form, extracts from Hericium mushroom species (e.g., H. erinaceus, H. coralloides, H. ramosum ) or combinations thereof, optionally one or more cannabinoids in pure form or extracts from Cannabis sativa, Cannabis sativa, Cannabis indica , or Cannabis ruderalis , optionally, one or more adversive compounds, and optionally one or more pharmaceutically acceptable excipients.