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2,5-Dimethoxy-4-chloroamphetamine (DOC) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized and documented in 1972 by Alexander Shulgin.

History[edit | edit source]

DOC was first synthesized by Alexander Shulgin. The synthesis was published in Shulgin's book PiHKAL. Shulgin listed DOC as a member of the "magical half-dozen" in his book PiHKAL: A Chemical Love Story. The six substances are: mescaline, DOM, DMT, 2C-B, 2C-E, and DOC.

Chemistry[edit | edit source]

DOC is a substituted amphetamine, specifically a derivative of DOx. It is structurally related to other drugs in the DOx family such as DOB and DOI. DOC is a chlorine substituted derivative of 2,5-dimethoxy-4-iodoamphetamine (DOI).

Pharmacology[edit | edit source]

DOC acts as a potent and selective 5-HT2A receptor partial agonist. Its effects are mediated by its affinity for the 5-HT2A receptor, much like other psychedelic amphetamines.

Effects[edit | edit source]

The effects of DOC are very dose-dependent and can vary greatly from person to person. Effects can include stimulation, open and closed-eye visuals, time distortion, enhanced introspection, and euphoria. The duration of effects can be up to 20 hours.

Legal status[edit | edit source]

In the United States, DOC is a Schedule I controlled substance. It is also illegal in many other countries under their respective controlled substances acts.

See also[edit | edit source]


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Contributors: Prab R. Tumpati, MD