2,5-dimethoxy-4-ethyl amphetamine

Snyder, S. H., Weingartner, H. and Faillace, L. A. (1970) DOET (2,5-Dimethoxy-4-ethyl-amphetamine) and DOM (2,5-Dimethoxy-4-methylamphetamine), new psychotropic agents. Their effects in man. In Psychotomimetic Drugs, D. H. Efron (Ed), Raven Press, New York, pp. 247-264. 

The three-carbon amphetamine analogue of 2C-F would quite logically be called DOF (2,5-dimethoxy-4-fluoroamphetamine). It has been prepared by reaction of the above benzaldehyde with nitroethane (giving l-(2,5-dimethoxy-4-fluorophenyl)-2-nitropropene, with a melting point of 128-129 °C from ethanol) followed by LAH reduction to DOF (the hydrochloride salt has a melting point of 166-167 °C, after recrystallization from ether/ethyl acetate/ethanol). Animal studies that have compared DOF to the highly potent DOI and DOB imply that the human activity will be some four to six times less than these two heavier halide analogues. As of the present time, no human trials of DOF have been made. 

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