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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. 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 experimental pharmaceutical drug.

Most compounds of this class are potent and long-lasting psychedelic drugs, and act as selective 5-HT2A, 5-HT2B, and 5-HT2C receptor agonists. 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.

DOx drugs like DOM have been associated with certain side effects that have not occurred to the same extent with other psychedelics like LSD. Examples of such side effects include physical symptoms like sweating, tremors, and large increases in heart rate.

The DOx drugs act as agonists of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. Their psychedelic effects are thought to be mediated specifically by activation of the serotonin 5-HT2A receptor.

In contrast to other amphetamines, DOx drugs like DOC, DOET, and DOM are inactive as monoamine releasing agents and reuptake inhibitors. Some of the DOx drugs, including DOB, DOET, DOI, and DOM, are agonists of the rat, rhesus monkey, and/or human trace amine-associated receptor 1 (TAAR1) with varying potencies.

In contrast to amphetamines like (–)-cathinone, but similarly to mescaline, DOM has shown no stimulant-like or reinforcing effects in rhesus monkeys. Conversely however, DOC has shown reinforcing effects, including conditioned place preference (CPP) and self-administration, in rodents similarly to methamphetamine. This is analogous to other findings in which various 2C and NBOMe drugs have been found to produce brain dopaminergic elevations and reinforcing effects in rodents.

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chemical class of substituted amphetamine
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