N-Methylserotonin
| N-Methylserotonin | |
|---|---|
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| IUPAC name 3-[2-(Methylamino)ethyl]-1H-indol-5-ol | |
| Other names Norbufotenin; Nω-Methylserotonin; N-Methyl-5-hydroxytryptamine | |
| Identifiers | |
| CAS number | 1134-01-6  |
| PubChem | 150885 |
| ChemSpider | 132989 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C11H14N2O |
| Molar mass | 190.24 g mol−1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
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)[1] and Zanthoxylum piperitum,[2] the Green and Golden Bell Frog, Litoria aurea,[3] and Amanita mushrooms.[4] 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.[1]
References
- ↑ 1.0 1.1 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. doi:10.1021/jf803298z. PMID 19049296.
- ↑ 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. doi:10.1271/bbb.100261. PMID 20834148.
- ↑ McClean, Stephen; Robinson, Robert C.; Shaw, Chris; Smyth, W. Franklin (2002). "Characterization and determination of indole alkaloids in frog-skin secretions by electrospray ionization ion trap mass spectrometry". Rapid Communications in Mass Spectrometry 16 (5): 346–354. doi:10.1002/rcm.583. PMID 11857717.
- ↑ 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.