DOx


4-Substituted-2,5-dimethoxyamphetamines 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.
The DOx family includes the following members:
StructureNameAbbreviation
2,5-Dimethoxy-4-amylamphetamineDOAM
2,5-Dimethoxy-4-bromoamphetamineDOB
2,5-Dimethoxy-4-butylamphetamineDOBU
2,5-Dimethoxy-4-chloroamphetamineDOC
2,5-Dimethoxy-4-ethoxyamphetamineMEM
2,5-Dimethoxy-4-ethylamphetamineDOET
2,5-Dimethoxy-4-ethylthioamphetamineAleph-2
2,5-Dimethoxy-4-fluoroamphetamineDOF
2,5-Dimethoxy-4-amphetamineDOEF
2,5-Dimethoxy-4-iodoamphetamineDOI
2,5-Dimethoxy-4-isopropylthioamphetamineAleph-4
2,5-Dimethoxy-4-methylamphetamineDOM
2,5-Dimethoxy-4-methylthioamphetamineAleph-1
2,5-Dimethoxy-4-nitroamphetamineDON
2,5-Dimethoxy-4-phenylthioamphetamineAleph-6
2,5-Dimethoxy-4-propylamphetamineDOPR
2,5-Dimethoxy-4-isopropylamphetamineDOiPR
2,5-Dimethoxy-4-propylthioamphetamineAleph-7
2,5-Dimethoxy-4-trifluoromethylamphetamineDOTFM

As well as the following members with additional substitutions: