Please use this identifier to cite or link to this item: doi:10.22028/D291-30908
Title: Interactions of phenethylamine‐derived psychoactive substances of the 2C‐series with human monoamine oxidases
Author(s): Wagmann, Lea
Brandt, Simon D.
Stratford, Alexander
Maurer, Hans H.
Meyer, Markus R.
Language: English
Title: Drug Testing and Analysis
Volume: 11
Startpage: 318
Endpage: 324
Publisher/Platform: Wiley
Year of Publication: 2018
Free key words: HILIC–HRMS/MS
drugs of abuse
IC50 value
monoamine oxidase inhibition
DDC notations: 500 Science
540 Chemistry
570 Life sciences, biology
Publikation type: Journal Article
Abstract: 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 is 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 12 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, and 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 were determined, values ranged from 10 to 125 μM (7 drugs) and from 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.
DOI of the first publication: 10.1002/dta.2494
Link to this record: urn:nbn:de:bsz:291--ds-309085
ISSN: 1942-7611
Date of registration: 5-Jun-2020
Faculty: M - Medizinische Fakultät
Department: M - Experimentelle und Klinische Pharmakologie und Toxikologie
Professorship: M - Prof. Dr. Markus Meyer
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