Cannabaceae

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N-Methylserotonin
Names
Preferred IUPAC name
3-[2-(Methylamino)ethyl]-1H-indol-5-ol
Other names
Norbufotenin; Nω-Methylserotonin; N-Methyl-5-hydroxytryptamine
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 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)[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-HT1A 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[edit]

United States[edit]

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[edit]

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[edit]

  1. ^ a b 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. 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.
  5. ^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  6. ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
source: https://en.wikipedia.org/wiki/N-Methylserotonin

One thought on “Cannabaceae”

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

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