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.
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Preferred IUPAC name
3-[2-(Methylamino)ethyl]-1H-indol-5-ol | |
Other names
Norbufotenin; Nω-Methylserotonin; N-Methyl-5-hydroxytryptamine
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Identifiers | |
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3D model (JSmol)
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ChEBI |
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ChemSpider |
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PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C11H14N2O | |
Molar mass | 190.246 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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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]
N-Methylserotonin is not scheduled at the federal level in the United States,[5] but could be considered an analog (of bufotenin), in which case, sales or possession intended for human consumption could be prosecuted under the Federal Analog Act.
N-Methylserotonin is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[6]
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