I put together a nice little document on this here: Post 440576 (https://www.thevespiary.org/talk/index.php?topic=12299.msg44057600#msg44057600)
(Rhodium: "Trip Tolerance: Neurons Swallowing own Receptors", Serious Chemistry) - Enjoy!
Electrochemical Study of the Hallucinogen (±)-1-(2,5-Dimethoxy-4-nitrophenyl)-2-aminopropane
Pablo Richter, Alfonso Morales and J. Sebastián Gómez-Jeria, Demián Morales-Lagos
The Analyst, 113, 859-863 (1988) (https://www.thevespiary.org/rhodium/Rhodium/pdf/don.electrostudy.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/don.electrostudy.pdf)
Abstract
An electrochemical study of the hallucinogen (±)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane, which differs from similar compounds in that a hydrophilic nitro group replaces hydrophobic substituents on the 4-position of the benzene ring, was carried out using a solvent - buffer system containing pyridine - formic acid and tetramethylammonium chloride solution. Polarographically and voltammetrically the drug behaves as other, structurally related aromatic nitro derivatives, the nitro group being reduced to the hydroxylamine in a single, well defined irreversible, diffusion-controlled and pH-dependent wave. The E1/2 versus pH and versus pH relationships were examined and cyclic voltammograms were recorded at different pH values and at different scan rates in order to elucidate the reduction mechanism and to identify relatively unstable intermediate species. The results of this study suggest that a significant relationship can be established between the electrochemical behaviour of any compound and its molecular - electronic structure, and between molecular structure and pharmaceutical or biological activity, as confirmed recently by quantitative structure - activity relationship studies.
A quantum-chemical and experimental study of the hallucinogen (±)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON)
Juan Sebastián Gomez-Jeria, Bruce K. Cassels and Juan Carlos Saavedra-Aguilar
Eur. J. Med. Chem. 22 (1987) 433-437
Abstract
The electronic structure of 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON) was calculated at the CNDO/2 level, and the racemic compound was synthesized and found to be hallucinogenic at doses of 4 mg. DON differs from its similarly active congeners in that a hydrophilic nitro group replaces lipophilic substituents at C-4 of the benzene ring. The implications for the mechanism of serotonin receptor binding of these drugs are discussed.
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)