2,5-Dimethoxy-4-fluoroamphetamine

2,5-Dimethoxy-4-fluoroamphetamine (DOF) is a serotonin receptor modulator and possible psychedelic drug of the phenethylamine, amphetamine, and DOx families. "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 1-(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." It is taken orally. The drug was encountered as a novel designer drug in Europe in 2015.

Use and effects In his books PiHKAL (Phenethylamines I Have Known and Loved) and The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds, Alexander Shulgin states that the properties and effects of DOF in humans are unknown. Based on animal studies however, specifically drug discrimination tests, he estimates that it would be 4- to 6-fold less potent than DOI and DOB as a psychedelic drug in humans. In his more book Phenethylamine: von der Struktur zur Funktion and other publications, Daniel Trachsel lists the dose of DOF as 10mg or more orally. He states that DOF produces stimulating effects at a dose of 6mg three times each spaced by 1hour (18mg total) orally based on initial anecdotal findings.

Interactions

Pharmacology Pharmacodynamics The receptor and transporter interactions of DOF have been characterized. As with other DOx drugs, it shows affinity for the serotonin 5-HT2 receptors and acts as a partial to full agonist of the serotonin 5-HT2A and 5-HT2B receptors. However, it shows much lower affinity for the serotonin 5-HT2 receptors than many other DOx drugs and a much lower degree of selectivity for the serotonin 5-HT2A receptor over the serotonin 5-HT1A receptor. On the other hand, the activational potencies of DOF at the serotonin 5-HT2A and 5-HT2B 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 4- to 6-fold lower potency than other DOx drugs like DOI and DOB.

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-HT2A 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.

Chemistry Synthesis The chemical synthesis of DOF has been described.

Analogues Analogues of DOF include DOI, DOB, DOC, DOTFM, 2C-F, and 25F-NBOMe, among others.

History DOF was first described in the scientific literature by Richard Glennon and colleagues by 1982. Subsequently, its properties and effects in humans were described by Daniel Trachsel in 2012. The drug was encountered as a novel designer drug in Slovenia in 2015.

Society and culture Legal status Canada DOF is a controlled substance in Canada under phenethylamine blanket-ban language.

United States DOF is not an explicitly controlled substance in the United States. However, it could be considered a Schedule I controlled substance as an analogue of DOM and DOB under the Federal Analogue Act in this country.

2,5-Dimethoxy-4-fluoroamphetamine

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