2,5-Dimethoxy-4-fluoroamphetamine (DOF) is a serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families.
Alexander Shulgin briefly describes DOF in his book PiHKAL (Phenethylamines I Have Known and Loved):
DOF showed some stimulating effects in humans, but no psychedelic effects, after three doses of 6mg orally spaced by one hour. Daniel Trachsel further suspected that the molar refraction of the important 4-substituent in DOF and 2C-F may be too low to activate the serotonin 5-HT<sub>2A</sub> receptor sufficiently to produce psychedelic effects. DOF more closely mimics the effects of the 4-unsubstituted 2,5-dimethoxyamphetamine than the effects of DOC, DOB, and DOI.
The receptor and transporter interactions of DOF have been characterized. As with other DOx drugs, it shows affinity for the serotonin 5-HT<sub>2</sub> receptors and acts as a partial to full agonist of the serotonin 5-HT<sub>2A</sub> and 5-HT<sub>2B</sub> receptors. However, it shows much lower affinity for the serotonin 5-HT<sub>2</sub> receptors than many other DOx drugs and a much lower degree of selectivity for the serotonin 5-HT<sub>2A</sub> receptor over the serotonin 5-HT<sub>1A</sub> receptor. On the other hand, the activational potencies of DOF at the serotonin 5-HT<sub>2A</sub> and 5-HT<sub>2B</sub> receptors were similar to those of DOB. The drug lacks significant affinity for the monoamine transporters (MATs), the human trace amine-associated receptor 1 (TAAR1), and various other receptors.
DOF substituted for DOM in rodent drug discrimination tests, albeit with lower potency than other DOx drugs.
The chemical synthesis of DOF has been described.
DOF was first described in the scientific literature by Richard Glennon and colleagues by 1982.
DOF is a controlled substance in Canada under phenethylamine blanket-ban language.