2-[[[2-(4-碘-2,5-二甲氧基苯基)乙基]氨基]甲基]苯酚 | 919797-20-9

• 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: 2-[[[2-(4-碘-2,5-二甲氧基苯基)乙基]氨基]甲基]苯酚
• 英文名称: 2-(((4-iodo-2,5-dimethoxyphenethyl)amino)methyl)phenol
• 英文别名: 25I-Nboh；2-[[2-(4-iodo-2,5-dimethoxyphenyl)ethylamino]methyl]phenol
• CAS: 919797-20-9
• 化学式: C₁₇H₂₀INO₃
• 分子量: 413.255
• InChiKey: FEUZHYRXGQTBRO-UHFFFAOYSA-N

物化性质

• 沸点：
  497.0±45.0 °C(Predicted)
• 密度：
  1.493±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[[[2-(4-碘-2,5-二甲氧基苯基)乙基]氨基]甲基]苯酚 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 N-(2-hydroxybenzyl)-4-iodo-2,5-dimethoxyphenethylamine hydrochloride
  参考文献：
  名称：

  25X-BOMes和25X-NBOHs（X = H，I，Br）的合成，用于药理研究和作为法医参考标准

  摘要：

  据报道，一种快速方法可合成三种NBOH（25H-，25I-和25B-NBOH；总产率为9–38％）和三种NBOM（25H-，25I-和25B-NBOMe；总产率为7–33％）。分别来自水杨醛和2-甲氧基醛。还确定了25H-，25I-和25B-NBOH.HCl的X射线结构。我们的方法应该为制备用于药理学和法医学目的的这类物质提供一个一般的入口。

  DOI：

  10.1016/j.tetlet.2020.152804
• 作为产物：
  描述：

  3-(2,5-二甲氧苯基)丙酸 在 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 sodium azide 、 四丁基溴化铵 、 zinc trifluoromethanesulfonate 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 2-[[[2-(4-碘-2,5-二甲氧基苯基)乙基]氨基]甲基]苯酚
  参考文献：
  名称：

  25C-NBOMe和25I-NBOMe代谢物生物标志物的合成与鉴定

  摘要：

  已经开发出用于合成25C-NBOMe和25I-NBOMe潜在代谢物的合成途径。已合成了九种潜在的代谢物，其中化合物8和20a可用作25C-NBOMe的代谢物生物标志物和25I-NBOMe的20b在法医实验室进行尿液检测以证明摄入量。

  DOI：

  10.1016/j.tet.2017.09.024

文献信息

• High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): A high-affinity 5-HT2A receptor-selective agonist radioligand
  作者：David E. Nichols、Stewart P. Frescas、Benjamin R. Chemel、Kenneth S. Rehder、Desong Zhong、Anita H. Lewin

  DOI：10.1016/j.bmc.2008.04.050

  日期：2008.6

  carrier added tritiated iodomethane in DMF with K(2)CO(3). Removal of the t-BOC protecting group and purification by HPLC afforded an overall yield of 43%, with a radiochemical purity of 99% and specific activity of 164Ci/mmol. The new radioligand was suitable for labeling human 5-HT(2A) receptors in two heterologous cell lines and had about 20-fold higher affinity than [(3)H]ketanserin.

  标题化合物 ([3H]INBMeO) 是通过 t-BOC 保护的二酚前体的 O,O-二甲基化反应制备的，不使用载体在 DMF 中添加氚化碘甲烷和 K(2)CO(3)。去除t-BOC保护基并通过HPLC纯化，总产率为43%，放射化学纯度为99%，比活为164Ci/mmol。新的放射性配体适用于标记两个异源细胞系中的人类 5-HT(2A) 受体，并且具有比 [(3)H] ketanserin 高约 20 倍的亲和力。
• Synthesis and Structure–Activity Relationships of <i>N</i>-Benzyl Phenethylamines as 5-HT_2A/2C Agonists
  作者：Martin Hansen、Karina Phonekeo、James S. Paine、Sebastian Leth-Petersen、Mikael Begtrup、Hans Bräuner-Osborne、Jesper L. Kristensen

  DOI：10.1021/cn400216u

  日期：2014.3.19

  N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5-dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule to determine the effects on receptor binding affinity and functional activity at 5-HT2A and 5-HT2c receptors. The compounds generally had high affinity for the 5-HT2A receptor with 8b having the highest affinity at 0.29 nM but with several other compounds also exhibiting subnanomolar binding affinities. The functional activity of the compounds was distributed over a wider range with lb being the most potent at 0.074 nM. Most of the compounds exhibited low to moderate selectivity (1- to 40-fold) for the 5-HT2A receptor in the binding assays, although one compound 6b showed an impressive 100-fold selectivity for the 5-HT2A receptor. In the functional assay, selectivity was generally higher with lb being more than 400-fold selective for the 5-HT2A receptor.
• COMPOSITIONS COMPRISING A PSILOCYBIN DERIVATIVE AND A CANNABINOID
  申请人：CaaMTech, LLC

  公开号：US20190142851A1

  公开（公告）日：2019-05-16

  This disclosure pertains to new compositions and methods comprising a psilocybin derivative. In one embodiment, the compositions disclosed herein are used for a method of regulating a neurotransmitter receptor, e.g., a serotonin receptor. In one embodiment, the compositions disclosed herein comprise purified compounds, e.g., a purified psilocybin derivative, a purified cannabinoid, or purified terpene.
• Synthesis of 25X-BOMes and 25X-NBOHs (X = H, I, Br) for pharmacological studies and as reference standards for forensic purposes
  作者：Wellington Alves de Barros、Marcelo Pereira Queiroz、Leonardo da Silva Neto、Graziele Martins Borges、Felipe Terra Martins、Ângelo de Fátima

  DOI：10.1016/j.tetlet.2020.152804

  日期：2021.3

  reported for the synthesis of three NBOHs (25H-, 25I- and 25B-NBOH; 9–38% overall yield) and three NBOMes (25H-, 25I- and 25B-NBOMe; 7–33% overall yield) from salicylaldehyde and 2-methoxyaldehyde, respectively. The X-ray structures of 25H-, 25I- and 25B-NBOH.HCl were also determined. Our approach should provide a general entry for preparing such a class of substances for pharmacological and forensic purposes

  据报道，一种快速方法可合成三种NBOH（25H-，25I-和25B-NBOH；总产率为9–38％）和三种NBOM（25H-，25I-和25B-NBOMe；总产率为7–33％）。分别来自水杨醛和2-甲氧基醛。还确定了25H-，25I-和25B-NBOH.HCl的X射线结构。我们的方法应该为制备用于药理学和法医学目的的这类物质提供一个一般的入口。
• Synthesis and identification of metabolite biomarkers of 25C-NBOMe and 25I-NBOMe
  作者：Xiongyu Wu、Caroline Eriksson、Ariane Wohlfarth、Jakob Wallgren、Robert Kronstrand、Martin Josefsson、Johan Dahlén、Peter Konradsson

  DOI：10.1016/j.tet.2017.09.024

  日期：2017.11

  Synthetic routes have been developed for synthesis of potential metabolites of 25C-NBOMe and 25I-NBOMe. Nine potential metabolites have been synthesized, among which compounds 8 and 20a could be used as metabolite biomarkers of 25C-NBOMe and 20b of 25I-NBOMe in urinary detection at forensic laboratories to prove intake.

  已经开发出用于合成25C-NBOMe和25I-NBOMe潜在代谢物的合成途径。已合成了九种潜在的代谢物，其中化合物8和20a可用作25C-NBOMe的代谢物生物标志物和25I-NBOMe的20b在法医实验室进行尿液检测以证明摄入量。