2,5-Dimethoxy-4-fluoroamphetamine

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2,5-Dimethoxy-4-fluoroamphetamine
2,5-Dimethoxy-4-fluoroamphetamine.svg
Systematic (IUPAC) name
(RS)-1-(4-fluoro-2,5-dimethoxy-phenyl)propan-2-amine
Clinical data
Legal status
Routes of
administration
Oral, Insufflation
Identifiers
CAS Registry Number 125903-69-7 N
ATC code None
PubChem CID: 23844155
ChemSpider 23108678 YesY
ChEMBL CHEMBL267526 YesY
Chemical data
Formula C11H16FNO2
Molecular mass 213.25 g/mol
 N (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:[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] 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.[3] 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 rather resembles the 4-unsubstituted 2,5-dimethoxyamphetamine than DOC, DOB or DOI.[5][6][7]

See also[edit]

References[edit]

  1. ^ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978. ISBN 0-9630096-0-5. 
  2. ^ Glennon RA, Young R, Benington F, Morin RD (October 1982). "Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry 25 (10): 1163–8. doi:10.1021/jm00352a013. PMID 7143352. 
  3. ^ D.E. Nichols (1991). Biochemistry and Physiology of Substance Abuse, Vol. III. Boca Raton, FL: CRC Press. 
  4. ^ Daniel Trachsel (July 2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis 4 (7-8): 577–590. doi:10.1002/dta.413. PMID 22374819. 
  5. ^ David E. Nichols, Stewart Frescas, Danuta Marona-Lewicka, Xuemei Huang, Bryan L. Roth, Gary A. Gudelsky, J. Frank Nash (December 1994). "1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist.". Journal of Medicinal Chemistry 37 (25): 4346–4351. doi:10.1021/jm00051a011. PMID 7996545. 
  6. ^ Richard A. Glennon (1991). "Discriminative stimulus properties of hallucinogens and related designer drugs.". NIDA Research Monograph 116: 25–44. PMID 1369672. 
  7. ^ Johnson MP1, Hoffman AJ, Nichols DE, Mathis CA. (December 1987). "Binding to the serotonin 5-HT2 receptor by the enantiomers of 125I-DOI.". Neuropharmacology 26 (12): 1803–1806. doi:10.1016/0028-3908(87)90138-9. PMID 3437942. 

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