5-MeO-NET

Chemical compound From Wikipedia, the free encyclopedia

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]

Other names5-Methoxy-N-ethyltryptamine
ATC code
  • None
Quick facts Clinical data, Other names ...
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
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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

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