2,5-Dimethoxyamphetamine (2,5-DMA), the base 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] 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.

DOx derivatives

The DOx family includes the following members:

Structure Name Abbreviation CAS number
2,5-Dimethoxy-4-amylamphetamine DOAM 63779-90-8
2,5-Dimethoxy-4-bromoamphetamine DOB 64638-07-9 (racemate)
2,5-Dimethoxy-4-butylamphetamine DOBU 63779-89-5
2,5-Dimethoxy-4-chloroamphetamine DOC 123431-31-2
2,5-Dimethoxy-4-ethoxyamphetamine MEM 16128-88-4
2,5-Dimethoxy-4-(methoxymethyl)amphetamine DOMOM [2] 260810-10-4
2,5-Dimethoxy-4-(ethoxymethyl)amphetamine DOMOE 930836-81-0
2,5-Dimethoxy-4-ethylamphetamine DOET 22004-32-6
2,5-Dimethoxy-4-ethylthioamphetamine Aleph-2 185562-00-9
2,5-Dimethoxy-4-fluoroamphetamine DOF 125903-69-7
2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine DOEF 121649-01-2
2,5-Dimethoxy-4-(3-fluoropropyl)amphetamine DOPF
2,5-Dimethoxy-4-iodoamphetamine DOI 42203-78-1
2,5-Dimethoxy-4-isopropylthioamphetamine Aleph-4 123643-26-5
2,5-Dimethoxy-4-methylamphetamine DOM 15588-95-1
2,5-Dimethoxy-4-methylthioamphetamine Aleph-1 61638-07-1
2,5-Dimethoxy-4-nitroamphetamine DON 67460-68-8
2,5-Dimethoxy-4-phenylthioamphetamine Aleph-6 952006-44-9
2,5-Dimethoxy-4-benzylamphetamine DOBZ [3] 125903-73-3
2,5-Dimethoxy-4-(3-methoxybenzyl)amphetamine DO3MeOBZ [4] 930836-90-1
2,5-Dimethoxy-4-[(tetrahydrofuran-2-yl)methyl]amphetamine DOTHFM 930776-12-8
2,5-Dimethoxy-4-propylamphetamine DOPR 63779-88-4
2,5-Dimethoxy-4-isopropylamphetamine DOiP 42306-96-7
2,5-Dimethoxy-4-propylthioamphetamine Aleph-7 207740-16-7
2,5-Dimethoxy-4-(difluoromethyl)amphetamine DODFM
2,5-Dimethoxy-4-trifluoromethylamphetamine DOTFM 159277-07-3
2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)amphetamine DOTFE [5]
2,5-Dimethoxy-4-cyanoamphetamine DOCN [6] 125903-74-4
2,5-Dimethoxy-4-ethynylamphetamine DOYN [7] 633290-70-7

A number of additional compounds are known with alternative substitutions:

Structure Name Abbreviation CAS number
Dimoxamine ("Ariadne") 4C-D 52842-59-8
1-(2,5-Dimethoxy-4-ethylphenyl)butan-2-amine [8] 4C-E
1-(2,5-Dimethoxy-4-(n-propyl)phenyl)butan-2-amine 4C-P
1-(2,5-Dimethoxy-4-bromophenyl)butan-2-amine 4C-B 69294-23-1
1-(2,5-Dimethoxy-4-chlorophenyl)butan-2-amine 4C-C 791010-74-7
1-(2,5-Dimethoxy-4-iodophenyl)butan-2-amine 4C-I 758631-75-3
1-(2,5-Dimethoxy-4-nitrophenyl)butan-2-amine 4C-N 775234-58-7
1-[2,5-Dimethoxy-4-(ethylthio)phenyl]butan-2-amine 4C-T-2 850007-13-5
Dimethoxymethamphetamine ("Beatrice") N-methyl-DOM 92206-37-6
2,5-Dimethoxy-3,4-methylenedioxyamphetamine DMMDA 15183-13-8
2,5-dimethoxy-3,4-dimethylamphetamine ("Ganesha") 3-methyl-DOM 207740-37-2
2,5-Dimethoxy-3,4-trimethylenylamphetamine G-3
2,5-Dimethoxy-3,4-tetramethylenylamphetamine G-4
2,5-Dimethoxy-3,4-norbornylamphetamine G-5
1-(5,8-dimethoxy-3,4-dihydro-1H-isochromen-7-yl)propan-2-amine [9] G-O 774538-38-4
2,5-Dimethoxy-3,4-dichloroamphetamine DODC 1373918-65-0
IDNNA IDNNA 67707-78-2
Methyl-DOB N-methyl-DOB 155638-80-5
2,3,4,5-Tetramethoxyamphetamine 2,3,4,5-Tetramethoxyamphetamine 23693-26-7
1-(4-Bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)propan-2-amine DOB-FLY 219986-75-1
Bromo-DragonFLY DOB-DFLY 502759-67-3
3-(4-bromo-2,5-dimethoxyphenyl)azetidine Compound 1,[10] ZC-B

See also

References

  1. ↑ Daniel Trachsel; David Lehmann & Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
  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. ↑ 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. ↑ Hellberg M, Namil A, Feng Z, Ward J. Phenylethylamine Analogs and Their Use for Treating Glaucoma. Patent WO 2007/038372, 6 Apr 2007
  5. ↑ Trachsel D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 1 Jul 2012, 4(7-8): 577-590.doi:10.1002/dta.413
  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. ↑ 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. ↑ Shulgin AT. Treatment of senile geriatric patients to restore performance. Patent US 4034113
  9. ↑ Hellberg MR, Namil A. Benzopyran analogs and their use for the treatment of glaucoma. Patent US 7396856
  10. ↑ Kristensen J, et al. 5-HT2A Agonists for Use in Treatment of Depression. Patent US 2021/0137908
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