N,N‐Diformylmescaline: A novel analogue of mescaline detected in Queensland

A novel analogue of mescaline, N,N-diformylmescaline, was identified in two unrelated drug seizures in Australia. A three-step synthesis from 3,4,5-trimethoxyphenylacetic acid was developed, but purification was difficult because the compound degrades in solution. Analysis by LC–MS showed instability under acidic and basic conditions, breaking down first to N-formylmescaline and then to mescaline when dissolved in hydrochloric acid for an extended period, suggesting it may act as a prodrug for mescaline. The paper presents GC–MS, NMR, and FTIR data for the seized compound, along with synthesis details and stability studies.

Study at a glance

Abstract

Abstract N,N ‐Diformylmescaline, a novel analogue of mescaline, has recently been detected in Australia in two unrelated seizures. To confirm the identification, a three‐step synthesis from 3,4,5‐trimethoxyphenylacetic acid was devised. However, purification of the final product proved problematic with the compound prone to degradation in solution. Analysis of the compound by LC–MS indicated that the compound was unstable under acidic and basic conditions, breaking down to N ‐formylmescaline. Further degradation to mescaline was observed when the compound was dissolved in hydrochloric acid for an extended period of time suggesting that N , N ‐diformylmescaline may be a prodrug for mescaline. The GC–MS, NMR and FTIR data for the seized compound are presented along with details of the synthesis and studies of the compound's stability in solution.