Chemistry:2,5-Dimethoxy-4-fluoroamphetamine

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Short description: Chemical compound
2,5-Dimethoxy-4-fluoroamphetamine
2,5-Dimethoxy-4-fluoroamphetamine.svg
Clinical data
Routes of
administration
Oral, Insufflation
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC11H16FNO2
Molar mass213.252 g·mol−1
3D model (JSmol)
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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:[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]

Alexander Shulgin, (PiHKAL)

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 5-HT2A receptor sufficiently.[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]

See also

  • 2,5-Dimethoxy-4-Substituted Amphetamines

References

  1. PiHKAL: A Chemical Love Story. United States: Transform Press. September 1991. pp. 978. ISBN 978-0-9630096-0-9. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml. 
  2. "Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry 25 (10): 1163–1168. October 1982. doi:10.1021/jm00352a013. PMID 7143352. 
  3. Biochemistry and Physiology of Substance Abuse, Vol. III. Boca Raton, Florida: CRC Press. 1991. 
  4. "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis 4 (7–8): 577–590. July 2012. doi:10.1002/dta.413. PMID 22374819. 
  5. "1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist". Journal of Medicinal Chemistry 37 (25): 4346–4351. December 1994. doi:10.1021/jm00051a011. PMID 7996545. 
  6. "Discriminative stimulus properties of hallucinogens and related designer drugs". NIDA Research Monograph 116 (116): 25–44. 1991. PMID 1369672. http://archives.drugabuse.gov/pdf/monographs/download116.html. Retrieved 2015-06-29. 
  7. "Binding to the serotonin 5-HT2 receptor by the enantiomers of 125I-DOI". Neuropharmacology 26 (12): 1803–1806. December 1987. doi:10.1016/0028-3908(87)90138-9. PMID 3437942.