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N-Methylserotonin is a tryptamine alkaloid. Chemically, it is a derivative of serotonin in which a methyl group resides at its alkyl amine. It is also called Nω-methylserotonin (Nω-methyl-5-hydroxytryptamine) to distinguish it from tryptamine-derived compounds in which a methyl group is bonded to the nitrogen atom of the indole group.
N-Methylserotonin is found in plants, animals, and fungi. These include the plants, Actaea racemosa (black cohosh) and Zanthoxylum piperitum, the Green and Golden Bell Frog, Litoria aurea, and Amanita mushrooms. The compound binds to several serotonin receptors, including the 5-HT7 and 5-HT1A receptors, with high affinity (IC50 ≤ 2 nM) and selectivity, and displays agonist activity; besides its direct interaction with the serotonin receptors, N-methylserotonin also acts as a selective serotonin reuptake inhibitor.
- Powell, SL; Gödecke, T; Nikolic, D; Chen, SN; Ahn, S; Dietz, B; Farnsworth, NR; Van Breemen, RB; Lankin, DC (2008). "In vitro serotonergic activity of black cohosh and identification of N(omega)-methylserotonin as a potential active constituent". Journal of Agricultural and Food Chemistry 56 (24): 11718–26. PMID 19049296. doi:10.1021/jf803298z.
- Yanase, E; Ohno, M; Harakawa, H; Nakatsuka, SI (2010). "Isolation of N,N-dimethyl and N-methylserotonin 5-O-β-glucosides from immature Zanthoxylum piperitum seeds". Bioscience, Biotechnology, and Biochemistry 74 (9): 1951–2. PMID 20834148. doi:10.1271/bbb.100261.
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- Tyler, V. E., Jr.; Groeger, D. (1964). "Amanita alkaloids. II. Amanita citrina and Amanita porphyria". Planta Medica 12 (4): 397–402. doi:10.1055/s-0028-1100193.