α-Methyltryptamine
[4][7][8] Side effects of αMT include agitation, restlessness, confusion, lethargy, pupil dilation, jaw clenching, and rapid heart rate, among others.[medical citation needed] With 20 to 30 mg, euphoria, empathy, and psychedelic effects become apparent and can last as long as 12 hours.[4][9] Physical manifestations including vomiting, mydriasis (pupillary dilation), jaw clenching, tachycardia, salivation, diaphoresis (sweating), and elevations in blood pressure, temperature, and respiratory rate.[4][9] Side effects self-reported by recreational users include anxiety, muscle tension, jaw tightness, pupil dilation, tachycardia, headaches, nausea, and vomiting, as well as psychedelic effects including visual hallucinations and an altered state of mind.[18] Fatalities verified with toxicology and autopsy include those of a 22-year-old man in Miami-Dade county and a British teenager, both of whom died after consuming 1 g of αMT.[21] αMT has been shown as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in vitro[26] and in vivo.[27] In rats, the potency of αMT as an MAO-A inhibitor in the brain was approximately equal to that of harmaline at equimolar doses.[30] A close analogue of αMT, α-ethyltryptamine (αET), is known to be a serotonergic neurotoxin similarly to MDMA and para-chloroamphetamine (PCA).[1][9] This alpha substitution makes it a relatively poor substrate for monoamine oxidase A, thereby prolonging αMT's half-life, allowing it to reach the brain and enter the central nervous system.[38][39][40] The synthesis of αMT can be accomplished through several different routes, the two most widely known being the nitroaldol condensation between indole-3-carboxaldehyde and nitroethane under ammonium acetate catalysis which produces 1-(3-indolyl)-2-nitropropene-1, the product can subsequently be reduced using a reducing agent like lithium aluminum hydride[41] The alternative synthesis is the condensation between indole-3-acetone and hydroxylamine.