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A quantum-chemical and experimental study of the hallucinogen (k)- 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON)

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1987-06-05
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Gómez Jeria, Juan
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A quantum-chemical and experimental study of the hallucinogen (k)- 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON)
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Author
  • Gómez Jeria, Juan;
  • Cassels Niven, Bruce;
  • Saavedra Aguilar, Juan Carlos;
Abstract
The electronic structure of 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON) was calculated at the CND0/2 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.
Patrocinador
(DIB Project Q 2442) and from the Chilean National Research Fund (Project 1075). One of us (J.S.G.-J.) thanks Drs. J. Maruani and A. Toro-LabbC for stimulating discussions.
Identifier
URI: https://repositorio.uchile.cl/handle/2250/119424
ISSN: 0223-5234.
Quote Item
Eur. J. Med. Chem. 22, 433-437, 1987.
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