2,5-Dimethoxy-4-fluoroamphetamine
Chemical compound
From Wikipedia, the free encyclopedia
2,5-Dimethoxy-4-fluoroamphetamine (DOF) is a serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families.[1][2]
- None
- CA: Schedule I
- UK: Class A
 | |
| Clinical data | |
|---|---|
| Other names | DOF; 2,5-Dimethoxy-4-fluoroamphetamine; 4-Fluoro-2,5-dimethoxyamphetamine |
| Routes of administration | Oral |
| ATC code |
|
| Legal status | |
| Legal status |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C11H16FNO2 |
| Molar mass | 213.252 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
Use and effects
Alexander Shulgin briefly describes DOF in his book PiHKAL (Phenethylamines I Have Known and Loved):[1]
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.[3]
— Alexander Shulgin, (PiHKAL)
DOF showed some stimulating effects in humans, but no psychedelic effects, after three doses of 6 mg orally spaced by one hour.[4] 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.[2] DOF more closely mimics the effects of the 4-unsubstituted 2,5-dimethoxyamphetamine than the effects of DOC, DOB, and DOI.[5][6][7]
Pharmacology
Pharmacodynamics
The receptor and transporter interactions of DOF have been characterized.[8][9][10][11] 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.[8][9][10][11] 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.[8][9][10][11] On the other hand, the activational potencies of DOF at the serotonin 5-HT2A and 5-HT2B receptors were similar to those of DOB.[11] The drug lacks significant affinity for the monoamine transporters (MATs), the human trace amine-associated receptor 1 (TAAR1), and various other receptors.[11]
DOF substituted for DOM in rodent drug discrimination tests, albeit with lower potency than other DOx drugs.[12]
Chemistry
Synthesis
The chemical synthesis of DOF has been described.[1]
History
DOF was first described in the scientific literature by Richard Glennon and colleagues by 1982.[13]
Society and culture
Legal status
Canada
DOF is a controlled substance in Canada under phenethylamine blanket-ban language.[14]