N-Methylserotonin

N-Methylserotonin 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

Names
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
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 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

United States

N-Methylserotonin is not scheduled at the federal level in the United States,[5] 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.[6]

References

1. 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. 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.
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. 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.CS1 maint: multiple names: authors list (link)
5. §1308.11 Schedule I.
6. Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL