5-MeO-NET

5-MeO-NET
Clinical data
Other names5-Methoxy-N-ethyltryptamine
Drug classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonin releasing agent[1][2]
ATC code
  • None
Identifiers
  • N-ethyl-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18N2O
Molar mass218.300 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]

Use and effects

5-MeO-NET was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved).[4]

Pharmacology

Pharmacodynamics

5-MeO-NET 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]

Chemistry

5-MeO-NET, chemically known as 5-methoxy-N-ethyltryptamine, is a synthetic substituted tryptamine and a N-Ethyltryptamine derivative.

Analogues

Analogues of 5-MeO-NET include N-Ethyltryptamine (NET), 4-HO-NET, 4-AcO-NET, αET, 4-HO-αET, 5-MeO-αET, 5-chloro-αMT (PAL-542), 5-fluoro-αET (PAL-545), 5-MeO-MET, 5-MeO-DMT, 5-MeO-DET, 5-MeO-MPT, 5-MeO-EPT, 5-MeO-MALT, and 5-MeO-MiPT, among others.[1]

History

5-MeO-NET was first described in the scientific literature by at least 1994.[3] Research on 5-MeO-NET since the early 2000s has primarily focused on its interactions with serotonin receptors and other targets, as well as behavioral effects in rodent models.[1][2]

See also

References

  1. ^ a b c d e f g Glatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M, et al. (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. ^ a b c d e 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. ^ a b Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, et al. (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.
  4. ^ Alexander T. Shulgin, Ann Shulgin (1997). TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press. ISBN 978-0-9630096-9-2. OCLC 38503252. Retrieved 30 January 2025.
allikas: https://en.wikipedia.org/wiki/5-MeO-NET