5-MeO-NET

Last updated
5-MeO-NET
MeO-NET.svg
Clinical data
Other names5-Methoxy-N-ethyltryptamine
Drug class Serotonin receptor agonist; Serotonin releasing agent [1] [2]
Identifiers
  • N'-ethyl-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C13H18N2O
Molar mass 218.300 g·mol−1
3D model (JSmol)
  • CCNCCc1c[nH]c2c1cc(OC)cc2
  • InChI=1S/C13H18N2O/c1-3-14-7-6-10-9-15-13-5-4-11(16-2)8-12(10)13/h4-5,8-9,14-15H,3,6-7H2,1-2H3
  • Key:UNPLGMNGAFLKSH-UHFFFAOYSA-N

5-MeO-NET, also known as 5-methoxy-N-ethyltryptamine, is a serotonin receptor agonist and serotonin releasing agent of the tryptamine family. [1] [2] [3] It is a potent full agonist or near-full agonist of the serotonin 5-HT1A, 5-HT2A, 5-HT2B, and 5-HT2C receptors. [1] [2] The drug is a relatively weak serotonin releasing agent. [2] It does not produce the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents, suggesting that it would not be hallucinogenic in humans. [1] However, 5-MeO-NET does produce the HTR if it is coadministered with a serotonin 5-HT1A receptor antagonist like WAY-100635, suggesting that its serotonin 5-HT1A receptor agonism masks or blocks its own serotonin 5-HT2A receptor-mediated HTR induction. [1] 5-MeO-NET was first described in the scientific literature by at least 1994. [3]

Contents

See also

References

  1. 1 2 3 4 5 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.
  2. 1 2 3 4 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.
  3. 1 2 Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, King A, Herrick-Davis K (June 1994). "Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines". Journal of Medicinal Chemistry. 37 (13): 1929–1935. doi:10.1021/jm00039a004. PMID   8027974.



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