DOx

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DOx

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.[1] Most compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonists. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT2 receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects.

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

DOx derivatives

The DOx family includes the following members:

More information Structure, Name ...

A number of additional compounds are known with alternative substitutions:

More information Structure, Name ...

See also

References

  1. [1]
    Daniel Trachsel; David Lehmann & Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
  2. [2]
    Harms A, Ulmer E, Kovar K. Synthesis and 5-HT2A radioligand receptor binding assays of DOMCl and DOMOM, two novel 5-HT2A receptor ligands. Arch. Pharm., 16 Jun 2003, 336(3): 155–158. doi:10.1002/ardp.200390014
  3. [3]
    Nelson DL, Lucaites VL, Wainscott DB, Glennon RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 1 Jan 1999, 359(1): 1–6. doi:10.1007/PL00005315
  4. [4]
    Hellberg M, Namil A, Feng Z, Ward J. Phenylethylamine Analogs and Their Use for Treating Glaucoma. Patent WO 2007/038372, 6 Apr 2007
  5. [5]
    Trachsel D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 1 Jul 2012, 4(7-8): 577-590.doi:10.1002/dta.413
  6. [6]
    Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33(3): 1032–1036. doi:10.1021/jm00165a023
  7. [7]
    Trachsel D (August 2003). "Synthesis of Novel (Phenylalkyl) amines for the Investigation of Structure–Activity Relationships, Part 3: 4‐Ethynyl‐2,5‐dimethoxyphenethylamine (= 4‐Ethynyl‐2, 5‐dimethoxybenzeneethanamine; 2C‐YN)". Helvetica Chimica Acta. 86 (8): 2754–9. doi:10.1002/hlca.200390224.
  8. [8]
    Shulgin AT. Treatment of senile geriatric patients to restore performance. Patent US 4034113
  9. [9]
    Hellberg MR, Namil A. Benzopyran analogs and their use for the treatment of glaucoma. Patent US 7396856
  10. [10]
    Kristensen J, et al. 5-HT2A Agonists for Use in Treatment of Depression. Patent US 2021/0137908
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