2,5-Dimethoxy-4-fluoroamphetamine

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DOF
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Clinical data
Other namesDOF; 2,5-Dimethoxy-4-fluoroamphetamine; 4-Fluoro-2,5-dimethoxyamphetamine
Routes of
administration		Oral
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  • None
Legal status
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Identifiers
  • 1-(4-fluoro-2,5-dimethoxyphenyl)propan-2-amine
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Chemical and physical data
FormulaC11H16FNO2
Molar mass213.252 g·mol−1
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  • CC(CC1=CC(=C(C=C1OC)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 checkY
  • Key:NRANUECGGQVXOT-UHFFFAOYSA-N checkY
Data page
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2,5-Dimethoxy-4-fluoroamphetamine (DOF) is a serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families.[1][2]

Use and effects

Alexander Shulgin briefly describes DOF in his book PiHKAL (Phenethylamines I Have Known and Loved):[1]

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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 effects, after three doses of 6 mg orally spaced by one hour.[4] 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

Pharmacodynamics

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 were 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]

Chemistry

Synthesis

The chemical synthesis of DOF has been described.[1]

History

DOF was first described in the scientific literature by Richard Glennon and colleagues by 1982.[13]

Society and culture

Canada

DOF is a controlled substance in Canada under phenethylamine blanket-ban language.[14]

See also

References

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  1. ^ a b c Page Module:Citation/CS1/styles.css has no content.Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978. ISBN 978-0-9630096-0-9.
  2. ^ a b Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ a b c Page Module:Citation/CS1/styles.css has no content.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. ^ a b c Page Module:Citation/CS1/styles.css has no content.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. ^ a b c Page Module:Citation/CS1/styles.css has no content.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. ^ a b c d e Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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.
  13. ^ Page Module:Citation/CS1/styles.css has no content.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". J Med Chem. 25 (10): 1163–1168. doi:10.1021/jm00352a013. PMID 7143352.
  14. ^ Page Module:Citation/CS1/styles.css has no content."Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

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