:N-Methylserotonin

{{DISPLAYTITLE:N-Methylserotonin}}

{{Chembox

| Name = N-Methylserotonin

| ImageFile = Norbufotenine.svg

| ImageSize = 200px

| PIN = 3-[2-(Methylamino)ethyl]-1H-indol-5-ol

| OtherNames = Norbufotenin; Norbufotenine; N_ω-Methylserotonin; N-Methyl-5-hydroxytryptamine; 5-Hydroxy-N-methyltryptamine; 5-HO-NMT; 5-OH-NMT; N-Me-5-HT

|Section1={{Chembox Identifiers

| CASNo = 1134-01-6

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = MZ25L5SJ6Z

| PubChem = 150885

| ChemSpiderID = 132989

| ChEBI = 48294

| SMILES = Oc1cc2c(cc1)[nH]cc2CCNC

| 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

| InChIKey = ASUSBMNYRHGZIG-UHFFFAOYAK

| StdInChI = 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

| StdInChIKey = ASUSBMNYRHGZIG-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=11 | H=14 | N=2 | O=1

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|Section3={{Chembox Hazards

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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.

N-Methylserotonin is found in plants, animals, and fungi. These include the plants, Actaea racemosa (black cohosh){{cite journal | pmid = 19049296 | year = 2008 | last1 = Powell | first1 = SL | last2 = Gödecke | first2 = T | last3 = Nikolic | first3 = D | last4 = Chen | first4 = SN | last5 = Ahn | first5 = S | last6 = Dietz | first6 = B | last7 = Farnsworth | first7 = NR | last8 = Van Breemen | first8 = RB | last9 = Lankin | first9 = DC | title = In vitro serotonergic activity of black cohosh and identification of N(omega)-methylserotonin as a potential active constituent | volume = 56 | issue = 24 | pages = 11718–26 | doi = 10.1021/jf803298z | journal = Journal of Agricultural and Food Chemistry | pmc=3684073}} and Zanthoxylum piperitum,{{cite journal | pmid = 20834148 | year = 2010 | last1 = Yanase | first1 = E | last2 = Ohno | first2 = M | last3 = Harakawa | first3 = H | last4 = Nakatsuka | first4 = SI | title = Isolation of N,N-dimethyl and N-methylserotonin 5-O-β-glucosides from immature Zanthoxylum piperitum seeds | volume = 74| issue = 9 | pages = 1951–2 | doi = 10.1271/bbb.100261| journal = Bioscience, Biotechnology, and Biochemistry| doi-access = | s2cid = 26028576 }} the Green and Golden Bell Frog, Litoria aurea,{{cite journal |author1=McClean, Stephen |author2=Robinson, Robert C. |author3=Shaw, Chris |author4=Smyth, W. Franklin | title = Characterization and determination of indole alkaloids in frog-skin secretions by electrospray ionization ion trap mass spectrometry | journal = Rapid Communications in Mass Spectrometry | year = 2002 | volume = 16 | issue = 5 | pages = 346–354 | doi = 10.1002/rcm.583 | pmid = 11857717|bibcode=2002RCMS...16..346M }} and Amanita mushrooms.{{cite journal | title = Amanita alkaloids. II. Amanita citrina and Amanita porphyria |author1=Tyler, V. E. Jr. |author2=Groeger, D. | journal = Planta Medica | year = 1964 | volume = 12 | issue = 4 | pages = 397–402 | doi = 10.1055/s-0028-1100193|s2cid=87540610 }} 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.