DOx explained

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:

StructureNameAbbreviationCAS number
2,5-Dimethoxy-4-amylamphetamineDOAM63779-90-8
2,5-Dimethoxy-4-bromoamphetamineDOB64638-07-9 (racemate)
2,5-Dimethoxy-4-butylamphetamineDOBU63779-89-5
2,5-Dimethoxy-4-chloroamphetamineDOC123431-31-2
2,5-Dimethoxy-4-ethoxyamphetamineMEM16128-88-4
2,5-Dimethoxy-4-(methoxymethyl)amphetamineDOMOM [2] 260810-10-4
2,5-Dimethoxy-4-(ethoxymethyl)amphetamineDOMOE930836-81-0
2,5-Dimethoxy-4-ethylamphetamineDOET22004-32-6
2,5-Dimethoxy-4-ethylthioamphetamineAleph-2185562-00-9
2,5-Dimethoxy-4-fluoroamphetamineDOF125903-69-7
2,5-Dimethoxy-4-(2-fluoroethyl)amphetamineDOEF121649-01-2
2,5-Dimethoxy-4-(3-fluoropropyl)amphetamineDOPF
2,5-Dimethoxy-4-iodoamphetamineDOI42203-78-1
2,5-Dimethoxy-4-isopropylthioamphetamineAleph-4123643-26-5
2,5-Dimethoxy-4-methylamphetamineDOM15588-95-1
2,5-Dimethoxy-4-methylthioamphetamineAleph-161638-07-1
2,5-Dimethoxy-4-nitroamphetamineDON67460-68-8
2,5-Dimethoxy-4-phenylthioamphetamineAleph-6952006-44-9
2,5-Dimethoxy-4-benzylamphetamineDOBZ [3] 125903-73-3
2,5-Dimethoxy-4-(3-methoxybenzyl)amphetamineDO3MeOBZ [4] 930836-90-1
2,5-Dimethoxy-4-[(tetrahydrofuran-2-yl)methyl]amphetamineDOTHFM930776-12-8
2,5-Dimethoxy-4-propylamphetamineDOPR63779-88-4
2,5-Dimethoxy-4-isopropylamphetamineDOiP42306-96-7
2,5-Dimethoxy-4-propylthioamphetamineAleph-7207740-16-7
2,5-Dimethoxy-4-(difluoromethyl)amphetamineDODFM
2,5-Dimethoxy-4-trifluoromethylamphetamineDOTFM159277-07-3
2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)amphetamineDOTFE [5]
2,5-Dimethoxy-4-cyanoamphetamineDOCN [6] 125903-74-4
2,5-Dimethoxy-4-ethynylamphetamine DOYN [7] 633290-70-7

Related compounds

A number of additional compounds are known with alternative substitutions:

StructureNameAbbreviationCAS number
Dimoxamine ("Ariadne")4C-D52842-59-8
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-amine4C-B69294-23-1
1-(2,5-Dimethoxy-4-chlorophenyl)butan-2-amine4C-C791010-74-7
1-(2,5-Dimethoxy-4-iodophenyl)butan-2-amine4C-I758631-75-3
1-(2,5-Dimethoxy-4-nitrophenyl)butan-2-amine4C-N775234-58-7
1-[2,5-Dimethoxy-4-(ethylthio)phenyl]butan-2-amine4C-T-2850007-13-5
Dimethoxymethamphetamine ("Beatrice")N-methyl-DOM92206-37-6
2,5-Dimethoxy-3,4-methylenedioxyamphetamineDMMDA15183-13-8
2,5-dimethoxy-3,4-dimethylamphetamine ("Ganesha")3-methyl-DOM207740-37-2
2,5-Dimethoxy-3,4-trimethylenylamphetamineG-3
2,5-Dimethoxy-3,4-tetramethylenylamphetamineG-4
2,5-Dimethoxy-3,4-norbornylamphetamineG-5
1-(5,8-dimethoxy-3,4-dihydro-1H-isochromen-7-yl)propan-2-amine [9] G-O774538-38-4
2,5-Dimethoxy-3,4-dichloroamphetamineDODC1373918-65-0
IDNNAIDNNA67707-78-2
Methyl-DOBN-methyl-DOB155638-80-5
2,3,4,5-Tetramethoxyamphetamine2,3,4,5-Tetramethoxyamphetamine23693-26-7
1-(4-Bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)propan-2-amineDOB-FLY219986-75-1
Bromo-DragonFLYDOB-DFLY502759-67-3
3-(4-bromo-2,5-dimethoxyphenyl)azetidine Compound 1,[10] ZC-B

See also

External links

Notes and References

  1. Book: Daniel Trachsel . David Lehmann . Christoph Enzensperger . amp . 2013 . Phenethylamine: Von der Struktur zur Funktion . Nachtschatten Verlag AG . 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.
  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.
  4. https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2007038372 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.
  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.
  7. Trachsel D . 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 . August 2003 . 86 . 8 . 2754–9 . 10.1002/hlca.200390224 .
  8. https://patents.google.com/patent/US4034113A Shulgin AT. Treatment of senile geriatric patients to restore performance. Patent US 4034113
  9. https://patents.google.com/patent/US7396856 Hellberg MR, Namil A. Benzopyran analogs and their use for the treatment of glaucoma. Patent US 7396856
  10. https://patentimages.storage.googleapis.com/a2/12/19/8424e3822cbe82/US20210137908A1.pdf Kristensen J, et al. 5-HT2A Agonists for Use in Treatment of Depression. Patent US 2021/0137908

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