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在手性池中畅游：源自丙氨酸前体的摇头丸和甲烯二氧甲基苯丙胺对映体。

Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors.

作者信息

Sherwood Alexander M, Burkhartzmeyer Elise K, Williamson Samuel E, Faley Michael T

机构信息

Usona Institute, 2780 Woods Hollow Rd, Madison, Wisconsin 53711, United States.

出版信息

ACS Omega. 2023 Jun 6;8(24):22132-22137. doi: 10.1021/acsomega.3c02358. eCollection 2023 Jun 20.

DOI:10.1021/acsomega.3c02358
PMID:37360440
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10286248/
Abstract

A divergent two-step process has provided access to optically pure enantiomers of MDMA and MDA, clinically relevant phenylisopropylamine entactogens. Target compounds were synthesized from commercially available alanine-derived aziridines. Critical process parameters were identified, and the reactions were optimized to avoid chromatographic purifications toward gram-scale isolations, providing ()-(-)-MDMA, ()-(+)-MDMA, ()-(-)-MDA, and ()-(+)-MDA each in greater than 98% purity by UPLC, >99% enantiomeric excess, and net yields between 50 and 60% for the complete process.

摘要

一种发散的两步法已能够合成出MDMA和MDA的光学纯对映体，这两种物质都是具有临床相关性的苯异丙胺类致幻剂。目标化合物由市售的丙氨酸衍生氮丙啶合成。确定了关键工艺参数，并对反应进行了优化，以避免进行色谱纯化以实现克级分离，通过超高效液相色谱法得到的（）-（-）-MDMA、（）-（+）-MDMA、（）-（-）-MDA和（）-（+）-MDA的纯度均大于98%，对映体过量大于99%，整个过程的净产率在50%至60%之间。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e84/10286248/2f9c959fabf1/ao3c02358_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e84/10286248/2de6b1977ea2/ao3c02358_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e84/10286248/6959455f67f1/ao3c02358_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e84/10286248/3f68db4fa870/ao3c02358_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e84/10286248/f9dea6279b23/ao3c02358_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e84/10286248/2f9c959fabf1/ao3c02358_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e84/10286248/2de6b1977ea2/ao3c02358_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e84/10286248/6959455f67f1/ao3c02358_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e84/10286248/3f68db4fa870/ao3c02358_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e84/10286248/f9dea6279b23/ao3c02358_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e84/10286248/2f9c959fabf1/ao3c02358_0004.jpg

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ACS Omega. 2021 Dec 20;7(1):900-907. doi: 10.1021/acsomega.1c05520. eCollection 2022 Jan 11.
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MDMA-assisted therapy for severe PTSD: a randomized, double-blind, placebo-controlled phase 3 study.MDMA 辅助治疗严重 PTSD：一项随机、双盲、安慰剂对照的 3 期研究。
Nat Med. 2021 Jun;27(6):1025-1033. doi: 10.1038/s41591-021-01336-3. Epub 2021 May 10.
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Effects of the Psychedelic Amphetamine MDA (3,4-Methylenedioxyamphetamine) in Healthy Volunteers.
健康志愿者中迷幻苯丙胺 MDA（3,4-亚甲二氧基苯丙胺）的影响。
J Psychoactive Drugs. 2019 Apr-Jun;51(2):108-117. doi: 10.1080/02791072.2019.1593560. Epub 2019 Apr 9.
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A Review of 3,4-methylenedioxymethamphetamine (MDMA)-Assisted Psychotherapy.3,4-亚甲基二氧甲基苯丙胺（摇头丸）辅助心理治疗综述。
Front Psychiatry. 2019 Mar 20;10:138. doi: 10.3389/fpsyt.2019.00138. eCollection 2019.
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Dark Classics in Chemical Neuroscience: 3,4-Methylenedioxymethamphetamine.化学神经科学中的黑暗经典：3,4-亚甲二氧基甲基苯丙胺。
ACS Chem Neurosci. 2018 Oct 17;9(10):2408-2427. doi: 10.1021/acschemneuro.8b00155. Epub 2018 Jul 12.
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