N-Methylserotonin

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:48294;
ChemSpider	132989;
PubChem CID	150885;
UNII	MZ25L5SJ6Z ;
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

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)^[1] and Zanthoxylum piperitum,^[2] the Green and Golden Bell Frog, Litoria aurea,^[3] and Amanita mushrooms.^[4]

Pharmacology

Pharmacodynamics

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.^[1]^[5] It also shows lower affinity for other serotonin receptors.^[1]^[5] It is a potent serotonin receptor agonist in the rat stomach strip.^[6] Besides its direct interaction with the serotonin receptors, N-methylserotonin acts as a selective serotonin reuptake inhibitor.^[1]

Chemistry

Analogues

Analogues of NMS (5-HO-NMT) include serotonin (5-HT), bufotenin (5-HO-DMT; N,N-dimethylserotonin), dimethyltryptamine (DMT), 4-HO-NMT, and α-methylserotonin (AMS; 5-HO-AMT), among others.

Society and culture

Legal status

United States

N-Methylserotonin is not scheduled at the federal level in the United States,^[7] 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.

Florida

N-Methylserotonin is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.^[8]

References

1 2 3 4 Powell, SL; Gödecke, T; Nikolic, D; Chen, SN; Ahn, S; Dietz, B; Farnsworth, NR; Van Breemen, RB; Lankin, DC (2008). "In vitro serotonergic activity of black cohosh and identification of N(omega)-methylserotonin as a potential active constituent". Journal of Agricultural and Food Chemistry. 56 (24): 11718–26. Bibcode:2008JAFC...5611718P. doi:10.1021/jf803298z. PMC 3684073. PMID 19049296.
↑ Yanase, E; Ohno, M; Harakawa, H; Nakatsuka, SI (2010). "Isolation of N,N-dimethyl and N-methylserotonin 5-O-β-glucosides from immature Zanthoxylum piperitum seeds". Bioscience, Biotechnology, and Biochemistry. 74 (9): 1951–2. doi:10.1271/bbb.100261. PMID 20834148. S2CID 26028576.
↑ McClean, Stephen; Robinson, Robert C.; Shaw, Chris; Smyth, W. Franklin (2002). "Characterization and determination of indole alkaloids in frog-skin secretions by electrospray ionization ion trap mass spectrometry". Rapid Communications in Mass Spectrometry. 16 (5): 346–354. Bibcode:2002RCMS...16..346M. doi:10.1002/rcm.583. PMID 11857717.
↑ Tyler, V. E. Jr.; Groeger, D. (1964). "Amanita alkaloids. II. Amanita citrina and Amanita porphyria". Planta Medica. 12 (4): 397–402. doi:10.1055/s-0028-1100193. S2CID 87540610.
1 2 Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID 3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
↑ Vane JR (March 1959). "The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation". Br J Pharmacol Chemother. 14 (1): 87–98. doi:10.1111/j.1476-5381.1959.tb00933.x. PMC 1481817. PMID 13651584.
↑ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
↑ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL

[Powell-1] 1 2 3 4 Powell, SL; Gödecke, T; Nikolic, D; Chen, SN; Ahn, S; Dietz, B; Farnsworth, NR; Van Breemen, RB; Lankin, DC (2008). "In vitro serotonergic activity of black cohosh and identification of N(omega)-methylserotonin as a potential active constituent". Journal of Agricultural and Food Chemistry. 56 (24): 11718–26. Bibcode:2008JAFC...5611718P. doi:10.1021/jf803298z. PMC 3684073. PMID 19049296.

[2] Yanase, E; Ohno, M; Harakawa, H; Nakatsuka, SI (2010). "Isolation of N,N-dimethyl and N-methylserotonin 5-O-β-glucosides from immature Zanthoxylum piperitum seeds". Bioscience, Biotechnology, and Biochemistry. 74 (9): 1951–2. doi:10.1271/bbb.100261. PMID 20834148. S2CID 26028576.

[3] McClean, Stephen; Robinson, Robert C.; Shaw, Chris; Smyth, W. Franklin (2002). "Characterization and determination of indole alkaloids in frog-skin secretions by electrospray ionization ion trap mass spectrometry". Rapid Communications in Mass Spectrometry. 16 (5): 346–354. Bibcode:2002RCMS...16..346M. doi:10.1002/rcm.583. PMID 11857717.

[4] Tyler, V. E. Jr.; Groeger, D. (1964). "Amanita alkaloids. II. Amanita citrina and Amanita porphyria". Planta Medica. 12 (4): 397–402. doi:10.1055/s-0028-1100193. S2CID 87540610.

[Glennon1987-5] 1 2 Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID 3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites

[Vane1959-6] Vane JR (March 1959). "The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation". Br J Pharmacol Chemother. 14 (1): 87–98. doi:10.1111/j.1476-5381.1959.tb00933.x. PMC 1481817. PMID 13651584.

[PART_1308_—_SCHEDULES_OF_CONTROLLED_SUBSTANCES_-_1308.11_Schedule_I-7] "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.

[Florida_Statutes_-_Chapter_893_-_DRUG_ABUSE_PREVENTION_AND_CONTROL-8] Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL

[1]