1-(2,5-Dimethoxy-4-methyl-phenyl)-2-nitro-propen | 29907-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2,5-Dimethoxy-4-methyl-phenyl)-2-nitro-propen
• 英文别名: 1,4-Dimethoxy-2-methyl-5-(2-nitroprop-1-enyl)benzene
• CAS: 29907-72-0
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: UCHNBPYWHXIUPN-UHFFFAOYSA-N

物化性质

• 沸点：
  368.7±37.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,5-Dimethoxy-4-methyl-phenyl)-2-nitro-propen 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 生成 (-)-DOM
  参考文献：
  名称：

  拟精神病药物1-（2,5-二甲氧基-4-甲基苯基）-2-氨基丙烷的体内代谢中的立体化学特征和代谢产物形成。

  摘要：

  DOI：

  10.1021/jm00254a019
• 作为产物：
  描述：

  硝基乙烷 、 2,5-二甲氧基-4-甲苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 生成 1-(2,5-Dimethoxy-4-methyl-phenyl)-2-nitro-propen
  参考文献：
  名称：

  致幻剂 1-(2,5-二甲氧基-4-甲基苯基)-2-氨基丙烷 (DOM) 四种可能的体外代谢物的合成

  摘要：

  描述了致幻剂 1-(2,5-二甲氧基-4-甲基苯基)-2-氨基丙烷 (DOM) 的四种可能体外代谢物的合成。这些化合物、1-(2,5-二甲氧基-4-甲基苯基(-2-丙酮、相应的肟、1-(2,5-二甲氧基-4-甲基苯基)-2-丙醇和1-(2,5 -二甲氧基)-4-甲基苯基-2-(羟氨基)丙烷，可能是DOM侧链代谢氧化的产物。

  DOI：

  10.1139/v74-063

文献信息

• The Synthesis of Four Possible in vitro Metabolites of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM)
  作者：Ronald T. Coutts、Jerry L. Malicky

  DOI：10.1139/v74-063

  日期：1974.2.1

  The synthesis of four possible in vitro metabolites of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) is described. These compounds, 1-(2,5-dimethoxy-4-methylphenyl(-2-propanone, the corresponding oxime, 1-(2,5-dimethoxy-4-methylphenyl)-2-propanol, and 1-(2,5-dimethoxy)-4-methylphenyl-2-(hydroxylamino)propane, could be products of side chain metabolic oxidation of DOM.

  描述了致幻剂 1-(2,5-二甲氧基-4-甲基苯基)-2-氨基丙烷 (DOM) 的四种可能体外代谢物的合成。这些化合物、1-(2,5-二甲氧基-4-甲基苯基(-2-丙酮、相应的肟、1-(2,5-二甲氧基-4-甲基苯基)-2-丙醇和1-(2,5 -二甲氧基)-4-甲基苯基-2-(羟氨基)丙烷，可能是DOM侧链代谢氧化的产物。
• N-Hydroxylation of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane by rabbit liver microsomes
  作者：J. Gal、L. D. Gruenke、N. Castagnoli

  DOI：10.1021/jm00241a007

  日期：1975.7

  Metabolic N-hydroxylation of the potent psychotomimetic amine 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (5) by rabbit liver microsomal preparations has been investigated. Synthetic hydroxylamine 8 was obtained by sequential reduction of the corresponding nitropropene 10 with sodium borohydride followed by zinc reduction of the resulting nitropropane 11. Compound 8 in water (pH 7.4) was rapidly

  研究了兔肝微粒体制剂对拟精神药胺1-（2,5-二甲氧基-4-甲基苯基）-2-氨基丙烷（5）的代谢N-羟基化作用。通过依次用硼氢化钠将相应的硝基丙烯10还原，然后将所得的硝基丙烷11进行锌还原，获得了合成的羟胺8。将化合物8在水中（pH 7.4）迅速空气氧化为肟12；在室温下将其氧化为肟12。兔肝微粒体完全阻止了这种氧化。胺5或其双（甲氧基-d3）六氘代类似物5-d6的微粒体温育分别形成8和8-d6，通过GLC-MS鉴定为它们的双（三氟乙酰基）衍生物。通过稳定的同位素稀释分析，以5-d6为底物，而8-d0为内标，通过使用选定的离子监测和加速电压交流发电机对代谢物的形成进行定量估计。以“拟外消旋体”（R）-5-d0：（S）-5-d6或（R）-5-d6：（S）-5-d0为底物的类似分析建立了代谢物8，使其R对映异构体富集。
• Structure-activity relations in psychotomimetic phenylalkylamines
  作者：F. A. B. Aldous、B. C. Barrass、K. Brewster、D. A. Buxton、D. M. Green、R. M. Pinder、P. Rich、M. Skeels、K. J. Tutt

  DOI：10.1021/jm00256a016

  日期：1974.10
• [EN] DIMETHOXYPHENYLALKYLAMINE ACTIVATORS OF SEROTONIN RECEPTORS<br/>[FR] ACTIVATEURS DE DIMÉTHOXYPHÉNYLALKYLAMINE DE RÉCEPTEURS DE LA SÉROTONINE
  申请人：[en]ATAI LIFE SCIENCES AG

  公开号：WO2022261240A2

  公开（公告）日：2022-12-15

  Provided herein are compounds of Formula (I), or pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, R6, and n are defined herein. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I) or pharmaceutically acceptable salt thereof, and methods of using a compound of Formula (I) or pharmaceutically acceptable salt thereof, e.g., in the treatment of a mental health disease or disorder.
• Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity
  作者：Richard A. Glennon、Reva Raghupathi、Piotr Bartyzel、Milt Teitler、Sigrun Leonhardt

  DOI：10.1021/jm00082a014

  日期：1992.2

  Certain phenylalkylamine derivatives have been considered to bind selectively at 5-HT2 serotonin receptors. It is now recognized that the most widely used derivatives, i.e., 1-(2,5-dimethoxy-4-X-phenyl)-2-aminopropanes where X = Me (DOM), Br (DOB), and I (DOI) (1-3, respectively) also bind at the more recently identified population of serotonin 5-HT1C receptors. The purpose of the present investigation was to determine whether simple phenylalkylamines bind selectively at one population of receptors over the other. An examination of 34 derivatives reveals (i) similar structure-affinity relationships and (ii) a significant correlation (r = > 0.9, n = 25) between 5-HT1C and 5-HT2 affinity. None of the compounds included in the present study displayed more than a 10-fold selectivity for one population of these receptors over the other; the results suggest that these compounds (including the widely used 5-HT2 agonists DOB and DOI) are 5-HT1C/5-HT2 agents.