2,5-Dimethoxy-4-iodoamphetamine

2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine. Unlike many other substituted amphetamines, however, it is not primarily a stimulant. DOI has a stereocenter and R-(−)-DOI is the more active stereoisomer.

Chemistry[edit | edit source]

DOI is a member of the 2C family of psychedelics that emerged onto the research chemical scene in the late 20th century. It is commonly synthesized from 2,5-dimethoxybenzaldehyde by condensation with nitroethane to give the nitrostyrene followed by reduction with lithium aluminum hydride or by using a reductive amination with a reducing agent like LAH.

Pharmacology[edit | edit source]

DOI acts as a highly potent full agonist for the human 5-HT2A receptor, making it a subtype of the 5-HT2 receptor family. This action at the 5-HT2A receptor, which is a G protein-coupled receptor, causes a release of inositol trisphosphate (IP3) which in turn activates protein kinase C. This leads to the release of calcium ions from the intracellular stores. This leads to a cellular response which includes the formation of inositol trisphosphate.

Effects[edit | edit source]

The effects of DOI are widely varied and can last from 16 to 30 hours. The drug is primarily used recreationally or for research purposes. It is often sold on blotter paper or in liquid solution. Effects can include significant changes in body temperature, heart rate, pupil dilation, nausea, introspective insights, visual and auditory hallucinations, and in rare cases, seizures.

Legal Status[edit | edit source]

In the United States, DOI is not scheduled at the federal level, though it could be considered an analog of 2C-B, which could make it illegal to buy, sell, or possess under the Federal Analog Act. In the United Kingdom, DOI is a Class A drug.