5-Methoxytryptamine

5-Methoxytryptamine (5-MT, 5-MeO-T, or 5-OMe-T), also known as serotonin methyl ether or O-methylserotonin and as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. It has been shown to occur naturally in the pineal gland of the brain. It is formed via O-methylation of serotonin or N-deacetylation of melatonin. 5-MT is a highly potent and non-selective serotonin receptor agonist and shows psychedelic-like effects in animals. However, it is inactive in humans, at least orally, likely due to rapid metabolism by monoamine oxidase (MAO). The levels and effects of 5-MT are dramatically potentiated by monoamine oxidase inhibitors (MAOIs) in animals. 5-MT was first described in the scientific literature by at least 1925. 5-MT is only briefly mentioned in Alexander Shulgin's TiHKAL (Tryptamines I Have Known and Loved) and its psychoactive effects are not described. Nonetheless, 5-MT has been said by other sources to produce mild psychoactive effects in humans. In addition, it has been reported to potentiate the effects of other drugs such as LSD and THC.