N -methyl serotonin

Structural formula
General
Surname	N-methylserotonin
other names	3- [2- (methylamino) ethyl] -1 H -indol-5-ol ( IUPAC ); 5-hydroxy- N -methyltryptamine; N ω -methyl serotonin; N ω -methyl-5-hydroxytryptamine; Norbufotenin;
Molecular formula	C 11 H 14 N 2 O
External identifiers / databases
PubChem	150885
Wikidata	Q855403
Drug information
Drug class	Tryptamines
properties
Molar mass	190.24 g · mol -1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

5-Hydroxy- N -methyltryptamine ( N -methylserotonin for short ), also norbufotenin, is an alkaloid from the tryptamine family. It is a derivative of serotonin . The designation N _ω -methylserotonin is also common to distinguish it from tryptamine-derived compounds in which a methyl group is bonded to the nitrogen atom of the indole group .

Occurrence

Silver grape candle (Actaea racemosa)

Golden tree frog (Litoria aurea)

N -Methylserotonin is found in plants, animals and fungi, including Actaea racemosa (silver grape candle), Zanthoxylum piperitum (Szechuan pepper), Litoria aurea (golden tree frog) and Amanita mushrooms ( amanita mushrooms ).

pharmacology

From a pharmacological point of view, N-methylserotonin binds to several serotonin receptors , including the 5-HT _1A and 5-HT ₇ receptors with high affinity ( IC ₅₀ ≤ 2 nM) and selectivity. In addition to serotonergic activity, the compound also acts as a serotonin reuptake inhibitor .

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ SL Powell, T. Gödecke, D. Nikolic, SN Chen, S. Ahn, B. Dietz, NR Farnsworth, RB van Breemen, DC Lankin, GF Pauli, JL Bolton: In vitro serotonergic activity of black cohosh and identification of N (omega) -methylserotonin as a potential active constituent. In: Journal of Agricultural and Food Chemistry . Volume 56, Number 24, December 2008, ISSN 1520-5118 , pp. 11718-11726, doi : 10.1021 / jf803298z . PMID 19049296 , PMC 3684073 (free full text).
↑ E Yanase, M Ohno, H Harakawa, SI Nakatsuka: Isolation of N , N -dimethyl and N -methylserotonin 5-O-β-glucosides from immature Zanthoxylum piperitum seeds . In: Bioscience, Biotechnology, and Biochemistry . 74, No. 9, 2010, pp. 1951-2. doi : 10.1271 / bbb.100261 . PMID 20834148 .
↑ McClean, Stephen; Robinson, Robert C .; Shaw, Chris; Smyth, W. Franklin: Characterization and determination of indole alkaloids in frog-skin secretions by electrospray ionization ion trap mass spectrometry . In: Rapid Communications in Mass Spectrometry . 16, No. 5, 2002, pp. 346-354. doi : 10.1002 / rcm.583 . PMID 11857717 .
↑ Tyler, VE, Jr .; Groeger, D .: Amanita alkaloid. II. Amanita citrina and Amanita porphyria . In: Planta Medica . 12, No. 4, 1964, pp. 397-402. doi : 10.1055 / s-0028-1100193 .

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Powell-2] SL Powell, T. Gödecke, D. Nikolic, SN Chen, S. Ahn, B. Dietz, NR Farnsworth, RB van Breemen, DC Lankin, GF Pauli, JL Bolton: In vitro serotonergic activity of black cohosh and identification of N (omega) -methylserotonin as a potential active constituent. In: Journal of Agricultural and Food Chemistry . Volume 56, Number 24, December 2008, ISSN 1520-5118 , pp. 11718-11726, doi : 10.1021 / jf803298z . PMID 19049296 , PMC 3684073 (free full text).

[3] E Yanase, M Ohno, H Harakawa, SI Nakatsuka: Isolation of N , N -dimethyl and N -methylserotonin 5-O-β-glucosides from immature Zanthoxylum piperitum seeds . In: Bioscience, Biotechnology, and Biochemistry . 74, No. 9, 2010, pp. 1951-2. doi : 10.1271 / bbb.100261 . PMID 20834148 .

[4] McClean, Stephen; Robinson, Robert C .; Shaw, Chris; Smyth, W. Franklin: Characterization and determination of indole alkaloids in frog-skin secretions by electrospray ionization ion trap mass spectrometry . In: Rapid Communications in Mass Spectrometry . 16, No. 5, 2002, pp. 346-354. doi : 10.1002 / rcm.583 . PMID 11857717 .

[5] Tyler, VE, Jr .; Groeger, D .: Amanita alkaloid. II. Amanita citrina and Amanita porphyria . In: Planta Medica . 12, No. 4, 1964, pp. 397-402. doi : 10.1055 / s-0028-1100193 .