DOx
Introduction 2,5-Dimethoxyamphetamine (2,5-DMA), the base structure of the DOx family'''4-Substituted-2,5-dimethoxyamphetamines''' ('''DO''x''''') 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. 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 DO''x'' family includes the following members: Structure Name Abbreviation CAS number 115px 2,5-Dimethoxy-4-amylamphetamine DOAM 63779-90-8 115px 2,5-Dimethoxy-4-bromoamphetamine DOB 64638-07-9 (racemate)  115px 2,5-Dimethoxy-4-butylamphetamine DOBU 63779-89-5 115px 2,5-Dimethoxy-4-chloroamphetamine DOC 123431-31-2 115px 2,5-Dimethoxy-4-ethoxyamphetamine MEM 16128-88-4 115px 2,5-Dimethoxy-4-(methoxymethyl)amphetamine DOMOM  260810-10-4 115px 2,5-Dimethoxy-4-(ethoxymethyl)amphetamine DOMOE 930836-81-0 115px 2,5-Dimethoxy-4-ethylamphetamine DOET 22004-32-6 115px 2,5-Dimethoxy-4-ethylthioamphetamine Aleph-2 185562-00-9 115px 2,5-Dimethoxy-4-fluoroamphetamine DOF 125903-69-7 115px 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine DOEF 121649-01-2 115px 2,5-Dimethoxy-4-(3-fluoropropyl)amphetamine DOPF  115px 2,5-Dimethoxy-4-iodoamphetamine DOI 42203-78-1 115px 2,5-Dimethoxy-4-isopropylthioamphetamine Aleph-4 123643-26-5 115px 2,5-Dimethoxy-4-methylamphetamine DOM 15588-95-1  115px 2,5-Dimethoxy-4-methylthioamphetamine Aleph-1 61638-07-1 115px 2,5-Dimethoxy-4-nitroamphetamine DON 67460-68-8 115px 2,5-Dimethoxy-4-phenylthioamphetamine Aleph-6 952006-44-9 115px 2,5-Dimethoxy-4-benzylamphetamine DOBZ  125903-73-3 115px 2,5-Dimethoxy-4-(3-methoxybenzyl)amphetamine DO3MeOBZ  930836-90-1 115px 2,5-Dimethoxy-4-(tetrahydrofuran-2-yl)methylamphetamine DOTHFM 930776-12-8 115px 2,5-Dimethoxy-4-propylamphetamine DOPR 63779-88-4 115px 2,5-Dimethoxy-4-isopropylamphetamine DOiP 42306-96-7 115px 2,5-Dimethoxy-4-propylthioamphetamine Aleph-7 207740-16-7 115px 2,5-Dimethoxy-4-(difluoromethyl)amphetamine DODFM 115px 2,5-Dimethoxy-4-trifluoromethylamphetamine DOTFM 159277-07-3 115px 2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)amphetamine DOTFE  115px 2,5-Dimethoxy-4-cyanoamphetamine DOCN  125903-74-4 115px 2,5-Dimethoxy-4-ethynylamphetamine  DOYN  633290-70-7
Related compounds A number of additional compounds are known with alternative substitutions: Structure Name Abbreviation CAS number 115px Dimoxamine ("Ariadne") 4C-D 52842-59-8 115px 1-(2,5-Dimethoxy-4-ethylphenyl)butan-2-amine  4C-E  115px 1-(2,5-Dimethoxy-4-(n-propyl)phenyl)butan-2-amine  4C-P  115px 1-(2,5-Dimethoxy-4-bromophenyl)butan-2-amine 4C-B 69294-23-1 115px 1-(2,5-Dimethoxy-4-chlorophenyl)butan-2-amine 4C-C 791010-74-7 115px 1-(2,5-Dimethoxy-4-iodophenyl)butan-2-amine 4C-I 758631-75-3 115px 1-(2,5-Dimethoxy-4-nitrophenyl)butan-2-amine 4C-N 775234-58-7 115px 1-2,5-Dimethoxy-4-(ethylthio)phenylbutan-2-amine 4C-T-2 850007-13-5 115px Dimethoxymethamphetamine ("Beatrice") N-methyl-DOM 92206-37-6 115px 2,5-Dimethoxy-3,4-methylenedioxyamphetamine DMMDA 15183-13-8 115px 2,5-dimethoxy-3,4-dimethylamphetamine ("Ganesha") 3-methyl-DOM 207740-37-2 115px 2,5-Dimethoxy-3,4-trimethylenylamphetamine G-3  115px 2,5-Dimethoxy-3,4-tetramethylenylamphetamine G-4  115px 2,5-Dimethoxy-3,4-norbornylamphetamine G-5  115px 1-(5,8-dimethoxy-3,4-dihydro-1H-isochromen-7-yl)propan-2-amine  G-O 774538-38-4 115px 2,5-Dimethoxy-3,4-dichloroamphetamine DODC 1373918-65-0 115px IDNNA IDNNA 67707-78-2 115px Methyl-DOB N-methyl-DOB 155638-80-5 115px 2,3,4,5-Tetramethoxyamphetamine 2,3,4,5-Tetramethoxyamphetamine 23693-26-7 115px 1-(4-Bromo-2,3,6,7-tetrahydrofuro2,3-f1benzofuran-8-yl)propan-2-amine DOB-FLY 219986-75-1  115px Bromo-DragonFLY DOB-DFLY 502759-67-3 115px 3-(4-bromo-2,5-dimethoxyphenyl)azetidine  Compound 1, ZC-B
See also * 2Cs, 25-NB* Substituted amphetamines* Substituted benzofurans* Substituted cathinones* Substituted methylenedioxyphenethylamines* Substituted phenethylamines* Substituted tryptamines
References
External links *  PiHKAL ("Phenethylamines I Have Known And Loved") by Alexander "Sasha" Shulgin (1991)*  Psychotomimetic Drugs: Structure-Activity Relationships by Alexander "Sasha" Shulgin (1978)