5,6-Methylenedioxy-N-methyl-2-aminoindane

5,6-Methylenedioxy-N-methyl-2-aminoindane (MDAI) is a psychoactive compound of the aminoindane class. It is known for its entactogenic effects similar to those of MDMA, although it is structurally distinct from MDMA in that it belongs to the aminoindane class of compounds. MDAI was first synthesized in the 1990s by a team led by David E. Nichols at Purdue University while investigating non-neurotoxic MDMA analogues.

Chemistry

MDAI is a synthetic compound with the chemical formula C₁₀H₁₁NO₂. It is a derivative of indane, a bicyclic structure composed of a benzene ring fused to a pentane ring. The methylenedioxy group (—CH₂O—CH₂—) is attached to the benzene ring, similar to the chemical structure of MDMA, which contributes to its entactogenic effects. The N-methyl group attached to the amino group makes it a tertiary amine.

Pharmacology

The pharmacological action of MDAI primarily involves its activity as a serotonin releasing agent (SRA). It is known to induce the release of serotonin, leading to mood elevation and empathogenic effects. Unlike MDMA, MDAI does not significantly release dopamine or norepinephrine, which is believed to contribute to its lower neurotoxic potential. The exact mechanism of action of MDAI is not fully understood, but it is thought to inhibit the reuptake of serotonin, thereby increasing its concentration in the synaptic cleft.

Effects

Users of MDAI report effects similar to those of MDMA, including enhanced mood, increased empathy, and mild euphoria. However, MDAI is generally considered to be less potent than MDMA, with a lower risk of negative side effects such as neurotoxicity, dehydration, and hyperthermia. The effects of MDAI can vary based on dosage, individual physiology, and the presence of other substances.

Legal Status

The legal status of MDAI varies by country. It has been classified as a controlled substance in several countries due to concerns about its potential for abuse and its similarity to MDMA. In some jurisdictions, MDAI falls under analogue drug laws, making its sale, possession, or use illegal.

Research

Research on MDAI has focused on its potential as a non-neurotoxic alternative to MDMA for use in psychotherapy and the study of the serotonin system. However, the research is limited, and more studies are needed to fully understand its pharmacological profile, efficacy, and safety.

See Also

• Phenethylamine
• Psychoactive drug
• Serotonin releasing agent
• David E. Nichols