Contents

N-Methylserotonin

N-Methylserotonin

Names
Preferred 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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48294
ChemSpider	132989
PubChem CID	150885
UNII	MZ25L5SJ6Z Y
CompTox Dashboard (EPA)	DTXSID40150396
InChI InChI=1S/C11H14N2O/c1-12-5-4-8-7-13-11-3-2-9(14)6-10(8)11/h2-3,6-7,12-14H,4-5H2,1H3 Key: ASUSBMNYRHGZIG-UHFFFAOYSA-N InChI=1/C11H14N2O/c1-12-5-4-8-7-13-11-3-2-9(14)6-10(8)11/h2-3,6-7,12-14H,4-5H2,1H3 Key: ASUSBMNYRHGZIG-UHFFFAOYAK
SMILES Oc1cc2c(cc1)[nH]cc2CCNC
Properties
Chemical formula	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

Chemical compound

N-Methylserotonin is a tryptamine alkaloid. Chemically, it is a derivativeofserotonin in which a methyl group resides at its alkyl amine. It is also called N_ω-methylserotonin (N_ω-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-HT_1A 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]

Legal Status[edit]

United States[edit]

N-Methylserotonin is not scheduled at the federal level in the United States,^[5] but could be considered an analog (ofbufotenin), in which case, sales or possession intended for human consumption could be prosecuted under the Federal Analog Act.

Florida[edit]

N-Methylserotonin is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.^[6]

References[edit]