(-)-Tenamfetamine | 61614-60-6

• 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: (R)-(-)-1-(1,3-benzodioxol-5-yl)-2-propanamine；(R)-(-)-3,4-(methylenedioxy)amphetamine；1-(1,3-benzodioxol-5-yl)propan-2-amine；(R)-3,4-methylenedioxyamphetamine；3,4-methylenedioxyamphetamine；(R)-MDA；(R)-alpha-Methyl-1,3-benzodioxole-5-ethanamine；(2R)-1-(1,3-benzodioxol-5-yl)propan-2-amine
• CAS: 61614-60-6
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: NGBBVGZWCFBOGO-SSDOTTSWSA-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-亚甲二氧基甲基苯丙胺已知的人类代谢物包括α-甲基多巴胺。

3,4-Methylenedioxymethamphetamine has known human metabolites that include Alpha-methyldopamine.

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 (-)-3,4-Methylenedioxymethamphetamine
  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-P₂-B₀₁ 、 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

• A turn-on fluorogenic probe for detection of MDMA from ecstasy tablets
  作者：Daniel Moreno、Borja Díaz de Greñu、Begoña García、Saturnino Ibeas、Tomás Torroba

  DOI：10.1039/c2cc17823k

  日期：——

  We report a fluorogenic probe that is able to discriminate a range of primary or secondary biogenic amines and their natural or synthetic mimics, in water or buffer, by means of the turn-on transient generation of green fluorescence, with high quantum yields and low detection limits, thus making the system suitable for the detection of abuse drugs, such as MDMA, from ecstasy tablets.

  我们报告了一种荧光探针，它能够在水或缓冲液中通过开启瞬时产生绿色荧光来分辨一系列伯胺或仲胺生物胺及其天然或合成模拟物，量子产率高，检测限低，因此该系统适用于检测摇头丸中的摇头丸等滥用药物。
• New bronchospasmolytic compounds and process for their preparation
  申请人：Aktiebolaget Draco

  公开号：EP0390762B1

  公开（公告）日：1994-01-19
• 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.
• [EN] NITRIC OXIDE RELEASING PRODRUGS OF MDA AND MDMA<br/>[FR] PROMÉDICAMENTS LIBÉRANT DE L'OXYDE NITRIQUE DE MDA ET MDMA
  申请人：[en]ATAI LIFE SCIENCES AG

  公开号：WO2023129958A2

  公开（公告）日：2023-07-06

  Provided herein are compounds of Formula (I), Formula (II), and Formula (III) or pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, R6, R7and A are defined herein. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I), Formula (II), or Formula (III) and methods of using a compound of Formula (I), Formula (II), or Formula (III), e.g., in the treatment of a mental health disease or disorder.
• METHODS OF MANUFACTURE OF R-MDMA
  申请人：Mind Medicine, Inc.

  公开号：US20240010628A1

  公开（公告）日：2024-01-11

  A method of manufacturing R-MDMA by forming a Grignard reagent from 5-bromobenzodioxole, treating the Grignard reagent with S-propylene oxide to form chirally pure alcohol 1, activating the alcohol as mesylate 2, converting to chirally pure azide 3, reducing the azide to amine 4, protecting the amine with di-tert-butyl dicarbonate, reducing the protected amine 5 to yield R-MDMA free base 6, and treating with an acid to form a salt 7 in >99% e.e. A method of manufacturing S-MDMA by forming a Grignard reagent from 5-bromobenzodioxole, treating the Grignard reagent with R-propylene oxide to form chirally pure alcohol 8, activating the alcohol as mesylate 9, converting to chirally pure azide 10, reducing the azide to amine 11, protecting the amine with di-tert-butyl dicarbonate, reducing the protected amine 12 to yield S-MDMA free base 13, and treating with an acid to form a salt 14 in >99% e.e.