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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. 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:

Structure Name Abbreviation
DOAM.png 2,5-Dimethoxy-4-amylamphetamine DOAM
DOB-racemic-skeletal.svg 2,5-Dimethoxy-4-bromoamphetamine DOB
DOBU.png 2,5-Dimethoxy-4-butylamphetamine DOBU
DOC-racemic-skeletal.svg 2,5-Dimethoxy-4-chloroamphetamine DOC
MEM.png 2,5-Dimethoxy-4-ethoxyamphetamine MEM
2,5-Dimethoxy-4-ethylamphetamine.svg 2,5-Dimethoxy-4-ethylamphetamine DOET
2,5-dimethoxy-4-ethylthioamphetamine.svg 2,5-Dimethoxy-4-ethylthioamphetamine Aleph-2
2,5-Dimethoxy-4-fluoroamphetamine.svg 2,5-Dimethoxy-4-fluoroamphetamine DOF
2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine.svg 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine DOEF
DOI-racemic-skeletal.svg 2,5-Dimethoxy-4-iodoamphetamine DOI
Aleph-4.svg 2,5-Dimethoxy-4-isopropylthioamphetamine Aleph-4
2,5-Dimethoxy-4-methylamphetamine.svg 2,5-Dimethoxy-4-methylamphetamine DOM
2,5-dimethoxy-4-methylthioamphetamine.svg 2,5-Dimethoxy-4-methylthioamphetamine Aleph-1
2,5-Dimethoxy-4-nitroamphetamine.svg 2,5-Dimethoxy-4-nitroamphetamine DON
Aleph-6.svg 2,5-Dimethoxy-4-phenylthioamphetamine Aleph-6
2,5-Dimethoxy-4-propylamphetamine.svg 2,5-Dimethoxy-4-propylamphetamine DOPR
DOiPR structure.png 2,5-Dimethoxy-4-isopropylamphetamine DOiPR
2,5-dimethoxy-4-propylthioamphetamine.svg 2,5-Dimethoxy-4-propylthioamphetamine Aleph-7
2,5-Dimethoxy-4-trifluoromethylamphetamine.svg 2,5-Dimethoxy-4-trifluoromethylamphetamine DOTFM

As well as the following members with additional substitutions:

See alsoEdit

ReferencesEdit

External linksEdit