2,5-Dimethoxy-4-fluoroamphetamine

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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
  • 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
 X mark.svgNYes check.svgY  (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]

—  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]

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 an agonist of these 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] 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

Related Research Articles

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<span class="mw-page-title-main">2,5-Dimethoxyamphetamine</span> Pharmaceutical compound

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DO<i>x</i> Class of chemical compounds

4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. They are 4-substituted derivatives of 2,5-dimethoxyamphetamine and are structurally related to the naturally occurring phenethylamine psychedelic mescaline.

<span class="mw-page-title-main">2C-T-16</span> Psychedelic drug

2C-T-16 is a lesser-known psychedelic drug. It was originally named by Alexander Shulgin as described in his book PiHKAL, however while Shulgin began synthesis of this compound he only got as far as the nitrostyrene intermediate, and did not complete the final synthetic step. Synthesis of 2C-T-16 was finally achieved by Daniel Trachsel some years later, and it was subsequently reported as showing similar psychedelic activity to related compounds, with a dose range of 10–25 mg and a duration of 4–6 hours, making it around the same potency as the better-known saturated analogue 2C-T-7, but with a significantly shorter duration of action. Binding studies in vitro showed 2C-T-16 to have a binding affinity of 44 nM at 5-HT2A and 15 nM at 5-HT2C. 2C-T-16 and related derivatives are potent partial agonists of the 5-HT1A, 5-HT2A, 5-HT2B and 5-HT2C receptors and induce a head-twitch response in mice.

<span class="mw-page-title-main">2,5-Dimethoxy-4-isopropylamphetamine</span> Chemical compound

2,5-Dimethoxy-4-isopropylamphetamine is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL. Shulgin described DOiPR as being at least an order of magnitude weaker than DOPr, with doses of 20–30 mg required to produce valid changes in mental state. Very little data exists about the pharmacological properties, metabolism, and toxicity of DOiPR.

<span class="mw-page-title-main">4C-B</span> Chemical compound

4C-B is a lesser-known psychedelic drug which is related to 2C-B and DOB. It is a reasonably potent 5-HT2A receptor partial agonist with a Ki of 7.6 nM, but has relatively low efficacy. It is briefly mentioned in Alexander Shulgin's book PiHKAL but was never tested by him, however it has subsequently been tested by Daniel Trachsel and colleagues and was found to be active in a dose range of 50 to 80 mg with a duration of around 8 hours, though with generally milder effects than 2C-B or DOB.

<span class="mw-page-title-main">3,4-Dimethoxyamphetamine</span> Pharmaceutical compound

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<span class="mw-page-title-main">2,5-Dimethoxy-4-cyanoamphetamine</span> Pharmaceutical compound

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<span class="mw-page-title-main">2,5-Dimethoxy-4-hexylamphetamine</span> Pharmaceutical compound

2,5-Dimethoxy-4-hexylamphetamine is a non-hallucinogenic serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families. It is part of the series of 4-alkylated DOx drugs that includes DOM (methyl), DOET (ethyl), DOPR (propyl), DOBU (butyl), and DOAM (amyl/pentyl), with DOHx having a hexyl substitution and hence the longest alkyl chain of the preceding drugs. After DOHx in the series is DOCT (octyl).

Richard A. Glennon, PhD is an American medicinal chemist who studies psychedelics, stimulants, entactogens, and other psychoactive drugs. He has been an important pioneer of the use of animal drug discrimination tests in scientific research for studying psychoactive drugs like hallucinogens. Glennon has also done a large amount of work on the structure–activity relationships of psychedelics. In addition, he played an important role in the discovery that the hallucinogenic effects of psychedelics are mediated by activation of serotonin 5-HT2 receptors. He is one of the most widely cited scientists in his field. Glennon was the editor-in-chief of the journal Medicinal Chemistry Research from 1992 to 2002. He retired in 2022 but has continued to publish reviews and research since then.

References

  1. ↑ Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978. ISBN   978-0-9630096-0-9.
  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): 1163–1168. doi:10.1021/jm00352a013. PMID   7143352.
  3. ↑ Nichols DE (1991). Biochemistry and Physiology of Substance Abuse, Vol. III. Boca Raton, Florida: CRC Press.
  4. ↑ Trachsel D (July 2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID   22374819.
  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 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.
  10. 1 2 3 4 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). doi: 10.1096/fasebj.2022.36.S1.R2121 . ISSN   0892-6638.
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