2,5-Dimethoxy-4-fluoroamphetamine

Use and effects

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-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.

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 was 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.

History

DOF was first described in the scientific literature by Richard Glennon and colleagues by 1982.

Society and culture

Legal status

Canada

DOF is a controlled substance in Canada under phenethylamine blanket-ban language.

References

References

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3. (1991). "Biochemistry and Physiology of Substance Abuse". CRC Press.
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6. (1991). "Discriminative stimulus properties of hallucinogens and related designer drugs". NIDA Research Monograph.
7. (December 1987). "Binding to the serotonin 5-HT2 receptor by the enantiomers of 125I-DOI". Neuropharmacology.
8. (June 1984). "5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA)". Eur J Pharmacol.
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10. (January 1999). "Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors". Naunyn Schmiedebergs Arch Pharmacol.
11. (2022). "Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues". The FASEB Journal.
12. (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships". NIDA Res Monogr.
13. (October 1982). "Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane". J Med Chem.
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