4-[(2R)-2-(甲基氨基)丙基]苯-1,2-二醇 | 20521-19-1

• 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: 4-[(2R)-2-(甲基氨基)丙基]苯-1,2-二醇
• 英文名称: (-)-DHMA
• 英文别名: (R)-3,4-dihydroxymethamphetamine；R-DHMA；1,2-Benzenediol, 4-((2R)-2-(methylamino)propyl)-；4-[(2R)-2-(methylamino)propyl]benzene-1,2-diol
• CAS: 20521-19-1
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: NTCPGTZTPGFNOM-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

ADMET

代谢

N-甲基-3,4-二羟基苯丙胺是已知的人类代谢物，来自于(S)-3,4-亚甲二氧基甲基苯丙胺。

N-Methyl-3,4- dihydroxyamphetamine is a known human metabolite of (R)-3,4-Methylenedioxymethamphetamine.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  (-)-3,4-Methylenedioxymethamphetamine 在 cytochrome P₄₅₀ 2D₆ Phe¹²⁰Ala mutant 作用下， 生成 4-[(2R)-2-(甲基氨基)丙基]苯-1,2-二醇 、 (R)-N-Hydroxy-Methylenedioxymethamphetamine 、 (-)-Tenamfetamine
  参考文献：
  名称：

  Metabolic Regio- and Stereoselectivity of Cytochrome P450 2D6 towards 3,4-Methylenedioxy-N-alkylamphetamines:  in Silico Predictions and Experimental Validation

  摘要：

  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.

  DOI：

  10.1021/jm050338+

文献信息

• MDMA PRODRUGS TO ASSIST PSYCHOTHERAPY
  申请人：Mind Medicine, Inc.

  公开号：US20220151986A1

  公开（公告）日：2022-05-19

  A compound including a prodrug having a psychoactive base substance attached to an amino acid. A method of treating an individual, especially in substance-assisted psychotherapy, by administering proMDMA or a proMDMA-like compound to the individual, metabolizing the prodrug, and releasing the MDMA or MDMA-like substance in the individual. A method of reducing anxiety while administering MDMA, by providing a slow release of MDMA or an MDMA-like substance and thereby reducing anxiety in the individual at the onset of administration. A method of personalized medicine, by evaluating an individual and determining if there are characteristics of the individual present that would not be suitable for MDMA treatment and administering proMDMA or a proMDMA-like substance to the individual. A method of reducing abuse of MDMA, by administering proMDMA or a proMDMA-like substance, and providing a delayed and attenuated effect of MDMA or a MDMA-like substance, thereby reducing abuse.
• [EN] ANORECTIC EPINEPHRINE DERIVATIVES<br/>[FR] DERIVES D'EPINEPHRINE ANOREXIQUES
  申请人：THE UNITED STATES OF AMERICA, represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：WO1994000432A1

  公开（公告）日：1994-01-06

  (EN) The present invention relates to certain novel piperidine-containing, substituted hydroxybenzyl alcohols and their pharmaceutically-acceptable salts (I). The invention further relates to pharmaceutical compositions useful for weigth reduction that alternatively contain as the active ingredient one of these chemical products or other substituted hydroxybenzyl alcohols, such as metaraminol, $g(a)-methylepinephrine, $g(a)-methylnorepinephrine, and N-substituted $g(a)-methylnorepinephrine related compounds of formula (II) where X = (a) and (b). The invention also relates to the use of these pharmaceutical compositions as anorectic agents for mammals.(FR) L'invention concerne certains nouveaux hydroxybenzylalcools substitués contenant de la piperidine et leurs sels pharmaceutiquement acceptable (I). L'invention concerne également des compositions pharmaceutiques de réduction du poids contenant alternativement, comme ingrédient actif, un de ces produits chimiques ou d'autres hydroxybenzylalcools substitués, tels que métaraminol, $g(a)-méthylènepinéphrine, $g(a)-méthylnorépinéphrine, et des composés apparentés à la $g(a)-méthylnorépinéphrine N-substitués de formule (II) où X représente (a) et (b). L'invention concerne également l'utilisation de ces compositions pharmaceutiques comme agents anoréxiques pour mammifères.
• [EN] SAMPLE COLLECTION DEVICES COMPRISING CONTROLS<br/>[FR] DISPOSITIF DE COLLECTE D'ÉCHANTILLONS COMPRENANT DES COMMANDES
  申请人：CONCATENO UK LTD

  公开号：WO2014033555A2

  公开（公告）日：2014-03-06

  Described herein are sample collection devices, which include a control for determining if the device is functioning properly and use thereof in conjunction with point of care tests.
• [EN] PHENETHYLAMINE DERIVATIVES, COMPOSITIONS, AND METHODS OF USE<br/>[FR] DÉRIVÉS DE PHÉNÉTYLAMINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：CYBIN IRL LTD

  公开号：WO2022038171A1

  公开（公告）日：2022-02-24

  There are disclosed psychedelic and entactogen compounds, the use of such compounds in the treatment of diseases associated with a serotonin 5-HT2 receptor, pharmaceutical compositions such as tablet compositions and kits containing the compounds, methods of delivering the compounds in a mist via inhalation, and methods of treating diseases or disorders associated with a serotonin 5-HT2 receptor, such as central nervous system (CNS) disorders or psychological disorders with the compounds of the invention.
• [EN] MDMA PRODRUGS TO ASSIST PSYCHOTHERAPY<br/>[FR] PROMÉDICAMENTS DE MDMA POUR AIDER À LA PSYCHOTHÉRAPIE
  申请人：[en]LIECHTI, Matthias Emanuel

  公开号：WO2022106947A1

  公开（公告）日：2022-05-27

  A compound including a prodrug having a psychoactive base substance attached to an amino acid. A method of treating an individual, especially in substance-assisted psychotherapy, by administering proMDMA or a proMDMA-like compound to the individual, metabolizing the prodrug, and releasing the MDMA or MDMA-like substance in the individual. A method of reducing anxiety while administering MDMA, by providing a slow release of MDMA or an MDMA-like substance and thereby reducing anxiety in the individual at the onset of administration. A method of personalized medicine, by evaluating an individual and determining if there are characteristics of the individual present that would not be suitable for MDMA treatment and administering proMDMA or a proMDMA-like substance to the individual. A method of reducing abuse of MDMA, by administering proMDMA or a proMDMA-like substance, and providing a delayed and attenuated effect of MDMA or a MDMA-like substance, thereby reducing abuse.