4-Bromo-3,5-dimethoxyamphetamine

4-Bromo-3,5-dimethoxyamphetamine

Chemical structure of 4-Bromo-3,5-dimethoxyamphetamine

3D model of 4-Bromo-3,5-dimethoxyamphetamine

4-Bromo-3,5-dimethoxyamphetamine (also known as DOB) is a psychedelic drug and a substituted amphetamine. It is a member of the phenethylamine and amphetamine chemical classes.

Chemical Structure

4-Bromo-3,5-dimethoxyamphetamine is a substituted amphetamine with the chemical formula C₁₁H₁₆BrNO₂. It features a bromine atom at the 4-position and two methoxy groups at the 3- and 5-positions of the phenyl ring.

Pharmacology

DOB acts as a serotonin receptor agonist, primarily targeting the 5-HT2A receptor. This action is responsible for its psychedelic effects. The compound is known for its potency and long duration of action, often lasting 12 to 24 hours.

Effects

The effects of 4-Bromo-3,5-dimethoxyamphetamine include altered perception, mood, and cognition. Users may experience visual and auditory hallucinations, changes in thought patterns, and an altered sense of time.

Synthesis

The synthesis of DOB involves the bromination of 3,5-dimethoxyphenylacetone followed by reductive amination with ammonia or a primary amine. This process requires careful control of reaction conditions to ensure the correct substitution pattern on the aromatic ring.

Legal Status

DOB is classified as a Schedule I controlled substance in many countries, including the United States, due to its potential for abuse and lack of accepted medical use.

Related Compounds

• 2,5-Dimethoxy-4-methylamphetamine (DOM)
• 2,5-Dimethoxy-4-iodoamphetamine (DOI)
• 2,5-Dimethoxy-4-ethylamphetamine (DOET)

See Also

• Psychedelic drug
• Serotonin receptor
• Phenethylamine

Related Pages

• Amphetamine
• Psychedelic research
• Hallucinogen

• 
  Chemical structure of 4-Bromo-3,5-dimethoxyamphetamine
• 
  3D model of 4-Bromo-3,5-dimethoxyamphetamine

• 
  Chemical structure of 4-Bromo-3,5-dimethoxyamphetamine
• 
  3D stick model of 4-Bromo-3,5-dimethoxyamphetamine