2,5-Dimethoxy-4-fluoroamphetamine

Last updated

DOF
DOF-2D-skeletal.svg
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
Formula C11H16FNO2
Molar mass 213.252 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 Yes check.svgY
  • Key:NRANUECGGQVXOT-UHFFFAOYSA-N Yes check.svgY
   (verify)

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

Contents

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. [3]

—  Alexander Shulgin, (PiHKAL)

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

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-HT2A and 5-HT2B 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-HT2A receptor over the serotonin 5-HT1A receptor. [8] [9] [10] [11] On the other hand, the activational potencies of DOF at the serotonin 5-HT2A and 5-HT2B 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]

See also

References

  1. 1 2 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978. ISBN   978-0-9630096-0-9.
  2. 1 2 Trachsel D (July 2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID   22374819.
  3. ↑ 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): 1163–1168. doi:10.1021/jm00352a013. PMID   7143352.
  4. ↑ Nichols DE, Oberlender R, McKenna DJ (1991). "Stereochemical Aspects of Hallucinogenesis". In Watson RR (ed.). Biochemistry and Physiology of Substance Abuse. Vol. 3. Boca Raton, Fla.: CRC Press. pp. 1–39. ISBN   978-0-8493-4463-3. OCLC   26748320.
  5. ↑ Nichols DE, Frescas S, Marona-Lewicka D, Huang X, Roth BL, Gudelsky GA, et al. (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. ↑ Glennon RA (1991). "Discriminative stimulus properties of hallucinogens and related designer drugs". NIDA Research Monograph. 116 (116): 25–44. PMID   1369672. Archived from the original on 2015-07-22. Retrieved 2015-06-29.
  7. ↑ Johnson MP, 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. S2CID   25077839.
  8. 1 2 3 Shannon M, Battaglia G, Glennon RA, Titeler M (June 1984). "5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA)". Eur J Pharmacol. 102 (1): 23–29. doi:10.1016/0014-2999(84)90333-9. PMID   6479216.
  9. 1 2 3 Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID   3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
  10. 1 2 3 Nelson DL, Lucaites VL, Wainscott DB, Glennon RA (January 1999). "Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors". Naunyn Schmiedebergs Arch Pharmacol. 359 (1): 1–6. doi:10.1007/pl00005315. PMID   9933142.
  11. 1 2 3 4 5 Rudin D, Luethi D, Hoener MC, Liechti ME (2022). "Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues". The FASEB Journal. 36 (S1) fasebj.2022.36.S1.R2121. doi: 10.1096/fasebj.2022.36.S1.R2121 . ISSN   0892-6638.
  12. ↑ Glennon RA (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships". NIDA Res Monogr. 94: 43–67. PMID   2575229.


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