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DOx

For other uses, see Dox.
2,5-Dimethoxyamphetamine (2,5-DMA), the base chemical structure of the DOx family.

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.[1][2] They are 4-substituted derivatives of 2,5-dimethoxyamphetamine (2,5-DMA, DOH) and are structurally related to the naturally occurring phenethylamine psychedelic mescaline.

The most well-known DOx drugs are DOM, DOI, DOB, DOET, and DOC.[3] DOI is widely used in scientific research.[2][4] DOM has been used as a recreational drug, while DOET was an experimental pharmaceutical drug.[5]

Most compounds of this class are potent and long-lasting psychedelic drugs, and act as selective 5-HT2A, 5-HT2B, and 5-HT2C receptor agonists.[6][7] A few bulkier derivatives such as DOAM have similarly high affinity for 5-HT2 receptors but have reduced activational efficacy and do not produce psychedelic effects.[2][6]

DOI has been found to have extraordinarily potent anti-inflammatory effects.[8][9][10] These properties are not shared by all other related drugs and appear to be mediated by functionally selective serotonin 5-HT2A receptor activation.[9][11] The anti-inflammatory effects of DOI and related drugs may have medical applications.[8][9]

  1. ^ Daniel Trachsel; David Lehmann & Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
  2. ^ a b c Cite error: The named reference GlennonDukat2024 was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference WillsErickson2012 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference CanalMorgan2012 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Baggott2023 was invoked but never defined (see the help page).
  6. ^ a b Cite error: The named reference LuethiRudinHoener2022 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference Ray2010 was invoked but never defined (see the help page).
  8. ^ a b Nichols DE, Johnson MW, Nichols CD (February 2017). "Psychedelics as Medicines: An Emerging New Paradigm". Clin Pharmacol Ther. 101 (2): 209–219. doi:10.1002/cpt.557. PMID 28019026.
  9. ^ a b c Flanagan TW, Nichols CD (August 2018). "Psychedelics as anti-inflammatory agents". Int Rev Psychiatry. 30 (4): 363–375. doi:10.1080/09540261.2018.1481827. PMID 30102081.
  10. ^ Yu B, Becnel J, Zerfaoui M, Rohatgi R, Boulares AH, Nichols CD (November 2008). "Serotonin 5-hydroxytryptamine(2A) receptor activation suppresses tumor necrosis factor-alpha-induced inflammation with extraordinary potency". J Pharmacol Exp Ther. 327 (2): 316–323. doi:10.1124/jpet.108.143461. PMID 18708586.
  11. ^ Flanagan TW, Foster TP, Galbato TE, Lum PY, Louie B, Song G, Halberstadt AL, Billac GB, Nichols CD (February 2024). "Serotonin-2 Receptor Agonists Produce Anti-inflammatory Effects through Functionally Selective Mechanisms That Involve the Suppression of Disease-Induced Arginase 1 Expression". ACS Pharmacol Transl Sci. 7 (2): 478–492. doi:10.1021/acsptsci.3c00297. PMC 10863441. PMID 38357283.

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