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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. [3] It has been shown to occur naturally in the body in low levels, especially in the pineal gland.
α-Methylmelatonin, also known as α-methyl-5-methoxy-N-acetyltryptamine, is a synthetic tryptamine derivative and analogue of the monoamine neurotransmitter melatonin. [1] It is a metabolite of α-methyltryptophan, α-methyl-5-hydroxytryptophan, and α-methylserotonin that can be formed in small amounts via aralkylamine N-acetyltransferase (AANAT).
The bioavailability of melatonin is between 2.5 and 50%. [6] [7] Melatonin is rapidly absorbed and distributed, reaching peak plasma concentrations after 60 minutes of administration, and is then eliminated. [6] Usual doses of exogenous melatonin of 1 to 12 mg produce melatonin concentrations 10 to 100 times higher than endogenous peak levels. [7]
In 1958, Aaron B. Lerner and his colleagues isolated the substance N-acetyl-5-methoxytryptamine and named it melatonin. [1] [7] High-affinity melatonin binding sites were pharmacologically characterized in the bovine brain in 1979. The first melatonergic receptor was cloned from melanophores of Xenopus laevis in 1994. [7]
Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. [9] [10] The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the first one being the heterocyclic nitrogen). [9]
Besides oxidative deamination by MAO into 5-HIAL, serotonin can also be conjugated by glucuronidation via glucuronyltransferases, conjugated by sulfation via sulfotransferases, acetylated and then methylated into melatonin (N-acetyl-5-methoxytryptamine) (which occurs mainly in the pineal gland), and converted into certain other metabolites like ...
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