(+)-MBDB | 103882-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (+)-MBDB
• 英文别名: (S)-(-)-N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine；(S)-Mbdb；(2S)-1-(1,3-benzodioxol-5-yl)-N-methylbutan-2-amine
• CAS: 103882-54-8
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: USWVWJSAJAEEHQ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

(2S)-1-(1,3-苯并二氧杂环戊基)-N-甲基-2-丁胺已知的人类代谢物包括1-(3,4-亚甲二氧基苯基)-2-丁胺和4-[2-(甲基氨基)丁基]苯-1,2-二醇。

(2S)-1-(1,3-Benzodioxol-5-yl)-N-methyl-2-butanamine has known human metabolites that include 1-(3,4-Methylenedioxyphenyl)-2-butanamine and 4-[2-(Methylamino)butyl]benzene-1,2-diol.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  (R)-1-Benzo[1,3]dioxol-5-yl-2-methylamino-butan-1-ol 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 (+)-MBDB
  参考文献：
  名称：

  Stereoselective Synthesis of (S)-3,4-Methylenedioxyamphetamines from (R)-Cyanohydrins

  摘要：

  AbstractA stereoselective synthesis of (S)‐3,4‐methylenedioxyamphetamines (S)‐7, which are highly interesting as psychoactive compounds, is described. Starting from readily available (R)‐cyanohydrins (R)‐2 the 2‐amino‐1‐aryl alcohols (1R,2S)‐4 were obtained with high diastereoselectivity by addition of Grignard reagents to the O‐protected cyanohydrins (R)‐3, transimination of the addition products A with primary amines, and hydrogenation of the imino intermediates B with NaBH4. For the hydrogenation of the benzylic hydroxyl group in the 1,2‐amino alcohols (1R,2S)‐4 a new, very efficient method was developed. The optically pure amphetamines (S)‐7 were obtained under very mild conditions by catalytic hydrogenation of the oxazolidinones (4S,5R)‐6, which were readily available by phosgenation of the amino alcohols (1R,2S)‐4.

  DOI：

  10.1002/chem.19970030825

文献信息

• Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class
  作者：David E. Nichols、Andrew J. Hoffman、Robert A. Oberlender、Peyton Jacob、Alexander T. Shulgin

  DOI：10.1021/jm00160a035

  日期：1986.10

  The alpha-ethyl phenethylamine derivative 1-(1,3-benzodioxol-5-yl)-2-butanamine was prepared. An asymmetric synthesis was used to prepare the enantiomers of this compound and the related alpha-methyl homologue (MDA). The racemates and enantiomers of both compounds were evaluated in the two-lever drug discrimination assay in rats trained to discriminate saline from 0.08 mg/kg of LSD tartrate. Stimulus generalization occurred with the racemate and the R-(-) enantiomer of the alpha-methyl homologue and the S-(+) enantiomer of the alpha-ethyl primary amine. No generalization occurred with the other enantiomers or with the N-methyl derivatives of either series. Human psychopharmacology studies revealed that the N-methyl derivative of the title compound was nonhallucinogenic and that it had a new, novel psychoactive effect. It is suggested that this compound is the prototype of a new pharmacologic class that may have value in facilitating psychotherapy and that this class be designated as entactogens.