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
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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
  • Oc1cc2c(cc1)[nH]cc2CCNC
Properties
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).

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 Nω-methylserotonin (Nω-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) and the Green and Golden Bell Frog, Litoria aurea, and Amanita mushrooms.

Pharmacology

Pharmacodynamics

The compound binds to several serotonin receptors, including the 5-HT7 and 5-HT1A receptors, with high affinity (IC50 ≤ 2 nM) and selectivity, and displays agonist activity. It also shows lower affinity for other serotonin receptors. It is a potent serotonin receptor agonist in the rat stomach strip. Besides its direct interaction with the serotonin receptors, N-methylserotonin acts as a serotonin reuptake inhibitor.

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

United States

N-Methylserotonin is not scheduled at the federal level in the United States, 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.

See also

References

  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. ↑ 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.
  3. ↑ 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.
  4. 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
  5. ↑ 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.
  6. ↑ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  7. ↑ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL