Topic summary

DOx

4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substitutedamphetaminederivatives featuring methoxygroups at the 2- and 5- positions of the phenylring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. They are 4-substituted derivatives of 2,5-dimethoxyamphetamine (2,5-DMA, DOH) and are structurally related to the naturally occurring phenethylamine psychedelic mescaline.

The most well-known DOx drugs are DOM, DOI, DOB, DOET, and DOC. DOI is widely used in scientific research. DOM has been used as a recreational drug, while DOET was an experimentalpharmaceutical drug.

Most compounds of this class are potent and long-lastingpsychedelicdrugs, and act as selective5-HT2A, 5-HT2B, and 5-HT2Creceptoragonists. A few bulkier derivatives such as DOAM have similarly high affinity for 5-HT2 receptors but have reduced efficacy and potency as psychedelics.

DOI has been found to have extraordinarily potent anti-inflammatory effects. These properties are not shared by all other related drugs and appear to be mediated by functionally selective serotonin 5-HT2A receptor activation. The anti-inflammatory effects of DOI and related drugs may have medical applications.