DOx
# DOx

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. Most compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective $5-HT_{2A},$ $5-HT_{2B},$ and $5-HT_{2C}$ receptor partial agonists. A few bulkier derivatives such as DOAM have similarly high binding affinity for $5-HT_2$ 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:

| 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 | 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 | 125903-73-3 |
| 2,5-Dimethoxy-4-(3-methoxybenzyl)amphetamine | DO3MeOBZ | 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 | |
| 2,5-Dimethoxy-4-cyanoamphetamine | DOCN | 125903-74-4 |
| 2,5-Dimethoxy-4-ethynylamphetamine | DOYN | 633290-70-7 |

## Related compounds

A number of additional compounds are known with alternative substitutions:

| Name | Abbreviation | CAS number |
| - | - | - |
| Dimoxamine ("Ariadne") | 4C-D | 52842-59-8 |
| 1-(2,5-Dimethoxy-4-ethylphenyl)butan-2-amine | 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 | 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, ZC-B | |
