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Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases

Wagmann, L, Brandt, SD, Stratford, A, Maurer, HH and Meyer, MR (2018) Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases. Drug Testing and Analysis, 11 (2). pp. 318-324. ISSN 1942-7611

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Psychoactive substances of the 2C-series (2Cs) are phenethylamine-derived designer drugs that can induce psychostimulant and hallucinogenic effects. Chemically, the classic 2Cs contain two methoxy groups in positions 2 and 5 of the phenyl ring, whereas substances of the so-called FLY series contain rigidified methoxy groups integrated in a 2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran core. One of the pharmacological features that has not been investigated in detail includes the inhibition of monoamine oxidase (MAO). Inhibition of this enzyme can cause elevated monoamine levels that have been associated with adverse events such as agitation, nausea, vomiting, tachycardia, hypertension, or seizures. The aim of this study was to extend the knowledge surrounding the potential of MAO inhibition for 17 test drugs, which consisted of twelve 2Cs (2C-B, 2C-D, 2C-E, 2C-H, 2C-I, 2C-N, 2C-P, 2C-T-2, 2C-T-7, 2C-T-21, bk-2C-B and bk-2C-I) and five FLY analogs (2C-B-FLY, 2C-E-FLY, 2C-EF-FLY, 2C-I-FLY, 2C-T-7-FLY). The extent of MAO inhibition was assessed using an established in vitro procedure based on heterologously expressed enzymes and analysis by hydrophilic interaction liquid chromatography-high resolution tandem mass spectrometry. Thirteen test drugs showed inhibition potential for MAO-A and 11 showed inhibition of MAO-B. In cases where MAO-A IC50 values could be determined, values ranged from 10 to 125 µM (7 drugs) and 1.7 to 180 µM for MAO-B (9 drugs). In the absence of detailed clinical information on most test drugs, it is concluded that a pharmacological contribution of MAO inhibition cannot be excluded and that further studies are warranted.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: Wagmann, L, Brandt, SD, Stratford, A, Maurer, HH, Meyer, MR. Interactions of phenethylamine‐derived psychoactive substances of the 2C‐series with human monoamine oxidases. Drug Test Anal. 2019; 11: 318– 324, which has been published in final form at https://doi.org/10.1002/dta.2494. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Uncontrolled Keywords: 0301 Analytical Chemistry, 1115 Pharmacology And Pharmaceutical Sciences
Subjects: R Medicine > RM Therapeutics. Pharmacology
R Medicine > RS Pharmacy and materia medica
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Wiley
Date Deposited: 04 Sep 2018 14:25
Last Modified: 04 Sep 2021 10:10
DOI or ID number: 10.1002/dta.2494
URI: https://researchonline.ljmu.ac.uk/id/eprint/9155
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