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N-Ethyltryptamine

From Wikipedia, the free encyclopedia
N-Ethyltryptamine
Clinical data
Other namesNET; NETP; Ethyltryptamine
ATC code
  • None
Legal status
Legal status
Identifiers
  • N-ethyl-2-(1H-indol-3-yl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H16N2
Molar mass188.274 g·mol−1
3D model (JSmol)
Melting point87 to 88 °C (189 to 190 °F)
  • CCNCCc1c[nH]c2ccccc12
  • InChI=1S/C12H16N2/c1-2-13-8-7-10-9-14-12-6-4-3-5-11(10)12/h3-6,9,13-14H,2,7-8H2,1H3 checkY
  • Key:TZWUSTVNAVKAPA-UHFFFAOYSA-N checkY
  (verify)

N-Ethyltryptamine (NET), also abbreviated as NETP, is a tryptamine that is structurally related to N-methyltryptamine (NMT) and the psychedelic drugs N,N-dimethyltryptamine (DMT) and N,N-diethyltryptamine (DET).[1]

Use and effects

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Alexander Shulgin included NET as an entry in his book TiHKAL (Tryptamines I Have Known and Loved).[1] However, he stated that it had been subjected only to modest human trials and that no active dose level had been identified.[1]

Pharmacology

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Pharmacodynamics

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NMT activities
TargetAffinity (Ki, nM)
5-HT1AIA
5-HT2A38 (EC50Tooltip half-maximal effective concentration)
99% (EmaxTooltip maximal efficacy)
SERT19a (EC50)
NETTooltip Norepinephrine transporter 3,862a (EC50)
DATTooltip Dopamine transporter 6,660a (EC50)
Notes: The smaller the value, the more avidly the drug interacts with the site. Footnotes: a = Neurotransmitter release. Sources: [2]

NET has been found to act as a potent serotonin 5-HT2A receptor full agonist and a selective serotonin releasing agent.[2] It is inactive at the 5-HT1A receptor.[2] The drug is also a serotonin receptor agonist in the rat uterus and stomach strip.[3][4]

Chemistry

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Synthesis

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The chemical synthesis of NET has been described.[1]

Analogues

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Analogues of NET include N-methyltryptamine (NMT), dimethyltryptamine (DMT), methylethyltryptamine (MET), and diethyltryptamine (DET), among others.[1]

Society and culture

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Canada

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NET is not a controlled substance in Canada as of 2025.[5]

See also

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References

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  1. 1 2 3 4 5 NET Entry in TIHKAL
  2. 1 2 3 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. ↑ Barlow RB, Khan I (March 1959). "Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations". Br J Pharmacol Chemother. 14 (1): 99–107. doi:10.1111/j.1476-5381.1959.tb00934.x. PMC 1481812. PMID 13651585.
  4. ↑ Vane JR (March 1959). "The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation". Br J Pharmacol Chemother. 14 (1): 87–98. doi:10.1111/j.1476-5381.1959.tb00933.x. PMC 1481817. PMID 13651584.
  5. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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