(+)-Tenamfetamine | 65620-66-8

• 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: (+)-Tenamfetamine
• 英文别名: (S)-(+)-1-(1,3-benzodioxol-5-yl)-2-propanamine；(S)-(+)-3,4-(methylenedioxy)amphetamine；1-(1,3-benzodioxol-5-yl)propan-2-amine；S-(+)-3,4-methylenedioxyamphetamine；(S)-3,4-methylenedioxyamphetamine；(S)-MDA；(S)-alpha-Methyl-1,3-benzodioxole-5-ethanamine；(2S)-1-(1,3-benzodioxol-5-yl)propan-2-amine
• CAS: 65620-66-8
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: NGBBVGZWCFBOGO-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

3,4-亚甲二氧基苯丙胺是已知的人类代谢物，来源于(S)-甲二氧基乙基苯丙胺。

3,4-methylenedioxyamphetamine is a known human metabolite of (S)-Methylenedioxyethylamphetamine.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  (+)-Tenamfetamine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 (S)-亚甲二氧基甲基苯丙胺; (S)-(+)-3,4-(亚甲二氧基)甲基苯丙胺
  参考文献：
  名称：

  Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class

  摘要：

  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.

  DOI：

  10.1021/jm00160a035
• 作为产物：
  描述：

  黄樟素 在 iron(III) chloride 、 palladium(II) trifluoroacetate 、 磷酸吡哆醛 、 amine transaminase TA-P₁-G₀₅ 、 sodium 2,2,2-trifluoroacetate 、 异丙胺 作用下， 以 aq. phosphate buffer 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 (+)-Tenamfetamine
  参考文献：
  名称：

  通过Wacker-Tsuji氧化-生物转氨顺序过程从烯丙基苯立体选择性合成1-芳基丙-2-胺

  摘要：

  本文介绍了一种顺序和选择性的化学酶法，涉及金属催化的烯丙基苯的Wacker-Tsuji氧化，然后由胺转氨酶催化的所得1-芳基丙烷-2-酮的生物氨基转移。因此，获得了九种光学活性的1-芳基丙烷-2-胺系列，在水性介质中具有良好至非常高的转化率（74-92％）和出色的选择性（对映体过量> 99％）。

  DOI：

  10.1002/adsc.201900179

文献信息

• IMMUNOASSAY FOR PYRROLIDINOPHENONES
  申请人：Randox Laboratories Limited

  公开号：US20130210167A1

  公开（公告）日：2013-08-15

  The invention describes antibodies that bind molecules of the pyrrolidinophenone class of synthetic drugs. The antibodies are derived from novel chemical intermediates, haptens and immunogens and are used in methods and kits to detect and quantify pyrrolidinophenones.

  该发明描述了能够结合合成药物吡咯烷基苯酮类分子的抗体。这些抗体来源于新型化学中间体、半抗原和免疫原，并用于检测和定量吡咯烷基苯酮的方法和试剂盒中。
• Immunoassay for pyrrolidinophenones
  申请人：Randox Laboratories Ltd.

  公开号：EP2626358B1

  公开（公告）日：2015-09-02
• Stereoselective Synthesis of (S)-3,4-Methylenedioxyamphetamines from (R)-Cyanohydrins
  作者：Franz Effenberger、Jürgen Jäger

  DOI：10.1002/chem.19970030825

  日期：1997.8

  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.
• Metabolic Regio- and Stereoselectivity of Cytochrome P450 2D6 towards 3,4-Methylenedioxy-<i>N</i>-alkylamphetamines:  in Silico Predictions and Experimental Validation
  作者：Peter H. J. Keizers、Chris de Graaf、Frans J. J. de Kanter、Chris Oostenbrink、K. Anton Feenstra、Jan N. M. Commandeur、Nico P. E. Vermeulen

  DOI：10.1021/jm050338+

  日期：2005.9.1

  A series of 3,4-methylenedioxy-N-alkylamphetamines (MDAAs) were automatically docked and subjected to molecular dynamics (MD) simulations in a cytochrome P450 2D6 (CYP2D6) protein model. The predicted substrate binding orientations, sites of oxidation, and relative reactivities were compared to the experimental data of wild-type and Phe(120)Ala mutant CYP2D6. Automated docking results were not sufficient to accurately rationalize experimental binding orientations of 3,4-methylenedioxy-N-methylamphetamine (MDMA) in the two enzymes as measured with spin lattice relaxation NMR. Nevertheless, the docking results could be used as starting structures for MD simulations. Predicted binding orientations of MDMA and sites of oxidation of the MDAAs derived from MD simulations matched well with the experimental data. It appeared the experimental results were best described in MD simulations considering the nitrogen atoms of the MDAAs in neutral form. Differences in regioselectivity and stereoselectivity in the oxidative metabolism of the MDAAs by the Phe(120)Ala mutant CYP2D6 were correctly predicted, and the effects of the Phe(120)Ala mutation could be rationalized as well.
• WO2023/81897
  申请人：——

  公开号：——

  公开（公告）日：——