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N-Methylserotonin

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 Zanthoxylum piperitum, 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. Besides its direct interaction with the serotonin receptors, N-methylserotonin acts as a selective 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.

References

References

  1. (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.
  2. (2010). "Isolation of ''N,N''-dimethyl and ''N''-methylserotonin 5-O-β-glucosides from immature ''Zanthoxylum piperitum'' seeds". Bioscience, Biotechnology, and Biochemistry.
  3. (2002). "Characterization and determination of indole alkaloids in frog-skin secretions by electrospray ionization ion trap mass spectrometry". Rapid Communications in Mass Spectrometry.
  4. (1964). "Amanita alkaloids. II. Amanita citrina and Amanita porphyria". Planta Medica.
  5. (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem.
  6. "§1308.11 Schedule I.".
  7. [http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL]
Info: Wikipedia Source

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5-ht1a-agonists 5-ht7-agonists n-monoalkyltryptamines 5-hydroxytryptamines serotonin-receptor-agonists
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