2,5-Dimethoxy-4-fluoroamphetamine

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2,5-Dimethoxy-4-fluoroamphetamine

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

Quick Facts Clinical data, Other names ...
DOF
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Clinical data
Other namesDOF; 2,5-Dimethoxy-4-fluoroamphetamine; 4-Fluoro-2,5-dimethoxyamphetamine
Routes of
administration
Oral, insufflation
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(4-Fluoro-2,5-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H16FNO2
Molar mass213.252 g·mol−1
3D model (JSmol)
  • CC(Cc1cc(c(cc1OC)F)OC)N
  • 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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Effects

Alexander Shulgin briefly describes DOF in his book PiHKAL:[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.[2]

DOF showed some stimulating effects in humans, but no psychedelic activity, after three doses of 6 mg spaced by one hour.[3] Researcher 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.[4] 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

The receptor and transporter interactions of DOF have been characterized.[8][9][10] 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] 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] On the other hand, the activational potencies of DOF at the serotonin 5-HT2A and 5-HT2B receptors was similar to those of DOB.[10] The drug lacks significant affinity for the monoamine transporters (MATs), the human trace amine-associated receptor 1 (TAAR1), and various other receptors.[10]

See also

References

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