2,5-Dimethoxy-4-fluoroamphetamine

2,5-Dimethoxy-4-fluoroamphetamine (DOF) is a serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families.^[1][2]

DOF

Clinical data
Other names	DOF; 2,5-Dimethoxy-4-fluoroamphetamine; 4-Fluoro-2,5-dimethoxyamphetamine
Routes of administration	Oral
ATC code	None
Legal status
Legal status	CA: Schedule I UK: Class A
Identifiers
IUPAC name 1-(4-fluoro-2,5-dimethoxyphenyl)propan-2-amine
CAS Number	125903-69-7 Y
PubChem CID	23844155
ChemSpider	23108678 Y
UNII	93WSW5GYR6
ChEMBL	ChEMBL267526 Y
CompTox Dashboard (EPA)	DTXSID90635906
Chemical and physical data
Formula	C11H16FNO2
Molar mass	213.252 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(Cc1cc(c(cc1OC)F)OC)N
InChI InChI=1S/C11H16FNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3 Y Key:NRANUECGGQVXOT-UHFFFAOYSA-N Y
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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-HT_2A 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-HT_2A and 5-HT_2B 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-HT_2A receptor over the serotonin 5-HT_1A receptor.^{[8][9][10][11]} On the other hand, the activational potencies of DOF at the serotonin 5-HT_2A and 5-HT_2B receptors was 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]

History

DOF was first described in the scientific literature by Richard Glennon and colleagues by 1982.^[13]

See also

• 2,5-Dimethoxy-4-substituted amphetamines (DOx)
• 2C-F
• 25F-NBOMe