Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors.
Alexander M. Sherwood, Elise K. Burkhartzmeyer, Samuel E. Williamson, Michael T. Faley
ACS Omega June 6, 2023 DOI: 10.1021/acsomega.3c02358 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | MDMA |
| Key points | The authors report a divergent two-step synthesis that converts alanine-derived aziridines into the individual enantiomers of MDMA and MDA without chromatographic purification, achieving gram-scale amounts of each with over 98% UPLC purity, over 99% enantiomeric excess, and 50-60% net yields. |
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 (R)-(-)-MDMA, (S)-(+)-MDMA, (R)-(-)-MDA, and (S)-(+)-MDA each in greater than 98% purity by UPLC, >99% enantiomeric excess, and net yields between 50 and 60% for the complete process.
Comparable studies
Other theoretical and historical papers on MDMA, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Differences Between the Mechanism of Action of MDMA, MBDB, and the Classic Hallucinogens. Identification of a New Therapeutic Class: Entactogens | 1986 | Theoretical or philosophical paper | |
| The Background and Chemistry of MDMA | 1986 | Historical analysis | |
| The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents* Original documents in Merck's historical archive in Darmstadt, Germany, years 1900–1960 | 2006 | Historical analysis | |
| Distinct neural mechanisms for the prosocial and rewarding properties of MDMA | 2019 | Theoretical or philosophical paper | |
| How could MDMA (ecstasy) help anxiety disorders? A neurobiological rationale | 2009 | Theoretical or philosophical paper |
Citations in the library
Cites 17
- MDMA-assisted therapy for severe PTSD: a randomized, double-blind, placebo-controlled phase 3 study. Nature Medicine June 1, 2021
- The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents* Addiction July 8, 2006
- Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class Journal of Medicinal Chemistry October 1, 1986
- A Review of 3,4-methylenedioxymethamphetamine (MDMA)-Assisted Psychotherapy Frontiers in Psychiatry March 20, 2019
- Dark Classics in Chemical Neuroscience: 3,4-Methylenedioxymethamphetamine ACS Chemical Neuroscience July 12, 2018
and 12 more in the library