2,5-Dimethoxy-4-fluoroamphetamine

2,5-Dimethoxy-4-fluoroamphetamine

Systematic (IUPAC) name
(RS)-1-(4-fluoro-2,5-dimethoxy-phenyl)propan-2-amine
Clinical data
Legal status	Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar laws in other countries)
Routes of administration	Oral, Insufflation
Identifiers
CAS Number	125903-69-7 N
ATC code	none
PubChem	CID: 23844155
ChemSpider	23108678 Y
ChEMBL	CHEMBL267526 Y
Chemical data
Formula	C11H16FNO2
Molecular mass	213.25 g/mol
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
NY (what is this?)  (verify)

2,5-Dimethoxy-4-fluoroamphetamine (DOF) is a psychedelic drug of the phenethylamine and amphetamine classes. Alexander Shulgin briefly describes DOF in his book PiHKAL:

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.

— Alexander Shulgin, (PiHKAL)

DOF showed some stimulating effects but no psychedelic activity at 3x6 mg (spaced by 1h, each) in humans. Trachsel further suspected that the molar refraction of the important 4-substituent in DOF and 2C-F may be too low to activate the 5-HT_2A receptor sufficiently. DOF rather resembles the 4-unsubstituted 2,5-dimethoxyamphetamine than DOC, DOB or DOI.

See also

• 2,5-Dimethoxy-4-Substituted Amphetamines

External links

• Synthesis of 4-Fluoro-2,5-Dimethoxyamphetamine (DOF)