N-Methylserotonin

N-Methylserotonin, also known as norbufotenin or as 5-hydroxy-N-methyltryptamine (5-HO-NMT), 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 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.

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N-Methylserotonin

Names
Preferred IUPAC name 3-[2-(Methylamino)ethyl]-1H-indol-5-ol
Other names Norbufotenin; Norbufotenine; Nω-Methylserotonin; N-Methyl-5-hydroxytryptamine; 5-Hydroxy-N-methyltryptamine; 5-HO-NMT; 5-OH-NMT; N-Me-5-HT
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

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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]