5-MeO-NMT

Last updated
5-MeO-NMT
5-MeO-NMT.svg
Names
Preferred IUPAC name
2-(5-Methoxy-1H-indol-3-yl)-N-methylethan-1-amine
Other names
5-Methoxy-N-methyltryptamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C12H16N2O/c1-13-6-5-9-8-14-12-4-3-10(15-2)7-11(9)12/h3-4,7-8,13-14H,5-6H2,1-2H3 Yes check.svgY
    Key: NFDDCRIHMZGWBP-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H16N2O/c1-13-6-5-9-8-14-12-4-3-10(15-2)7-11(9)12/h3-4,7-8,13-14H,5-6H2,1-2H3
    Key: NFDDCRIHMZGWBP-UHFFFAOYAI
  • CNCCC1=CNC2=CC=C(C=C21)OC
Properties
C12H16N2O
Molar mass 204.273 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

5-MeO-NMT (5-methoxy-N-methyltryptamine) is an organic chemical compound, being the 5-methoxy analog of N-methyltryptamine (NMT). It was first isolated from Phalaris arundinacea (reed canary grass). [1] It has also been synthesized by Alexander Shulgin and reported in his book TiHKAL . [2]

Contents

Pharmacology

5-MeO-NMT is a potent agonist of the serotonin 5-HT1A, 5-HT2A, 5-HT2B, and 5-HT2C receptors. [3] It is a full agonist or near-full agonist of all of these receptors except for the serotonin 5-HT2A receptor, where it is a partial agonist. [3] The drug is also a very weak serotonin releasing agent. [3] [4]

5-MeO-NMT does not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [3] On the other hand, it does induce serotonin 5-HT1A receptor-mediated hypothermia and hypolocomotion. [3]

Chemistry

Notable analogues of 5-MeO-NMT include NMT, 5-MeO-NET, 5-MeO-NiPT, norpsilocin (4-HO-NMT), baeocystin (4-PO-NMT), 4-HO-NALT, and 5-MeO-NBpBrT, among others. [3] [4]

In the United States, this substance is a Schedule 1 analogue of bufotenin.

See also

References

  1. ↑ Wilkinson, S. (1958). "428. 5-Methoxy-N-methyltryptamine: a new indole alkaloid from Phalaris arundinacea L.". Journal of the Chemical Society (Resumed): 2079. doi:10.1039/jr9580002079.
  2. ↑ 5-MeO-NMT Entry in TIHKAL
  3. 1 2 3 4 5 6 Glatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M, Golen JA, Chadeayne AR, Manke DR, Blough BE, McCorvy JD, Baumann MH (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice". ACS Chem Neurosci. 15 (24): 4458–4477. doi:10.1021/acschemneuro.4c00513. PMID   39636099.
  4. 1 2 Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC   4194234 . PMID   24800892.


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.