DOx

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Overview

The DOx class of compounds refers to a group of psychedelic phenethylamines that are structurally related to 2,5-dimethoxyamphetamine (2,5-DMA). These compounds are known for their potent hallucinogenic effects and are often used in psychedelic research and recreational settings. The DOx series includes several well-known substances such as DOB, DOC, and DOI.

Structure of 2,5-Dimethoxyamphetamine (2,5-DMA)

Chemical Structure

The DOx compounds are characterized by the presence of a 2,5-dimethoxy substitution pattern on the phenyl ring and an alpha-methyl group on the side chain, similar to amphetamine. The "x" in DOx represents a halogen or other substituent at the 4-position of the phenyl ring, which can significantly alter the compound's potency and effects.

Pharmacology

DOx compounds act primarily as serotonin receptor agonists, particularly at the 5-HT2A receptor, which is believed to be responsible for their psychedelic effects. They may also interact with other serotonin receptors and have varying degrees of activity at dopamine and norepinephrine receptors.

Effects

The effects of DOx compounds can vary widely depending on the specific compound and dosage. Common effects include altered perception of time and space, visual and auditory hallucinations, and changes in mood and thought processes. These compounds are known for their long duration of action, often lasting 12-24 hours or more.

Common DOx Compounds

DOB

Structure of DOB

DOB (2,5-dimethoxy-4-bromoamphetamine) is one of the most well-known DOx compounds. It is known for its strong psychedelic effects and long duration.

DOC

Structure of DOC

DOC (2,5-dimethoxy-4-chloroamphetamine) is another popular DOx compound, known for its intense visual effects and long-lasting experience.

DOI

DOI (2,5-dimethoxy-4-iodoamphetamine) is similar to DOB and DOC in its effects and duration, with a reputation for producing vivid visual hallucinations.

Other Variants

Other less common DOx compounds include DOAM, DOBU, MEM, DOMOM, and DOMOE. Each of these has unique properties and effects, contributing to the diversity of experiences within the DOx class.

Structure of DOAM
Structure of DOBU
Structure of MEM
Structure of DOMOM
Structure of DOMOE

Safety and Legal Status

The safety profile of DOx compounds is not well-established, and they can pose significant risks, especially at high doses. Potential adverse effects include hypertension, tachycardia, anxiety, and psychosis. The legal status of DOx compounds varies by country, with many being classified as controlled substances due to their potential for abuse and lack of medical use.

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Contributors: Prab R. Tumpati, MD