N-Ethyltryptamine

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]

N-Ethyltryptamine

Clinical data
Other names	NET; NETP; Ethyltryptamine
ATC code	None
Legal status
Legal status	US: Schedule I (isomer of DMT)
Identifiers
IUPAC name N-ethyl-2-(1H-indol-3-yl)ethan-1-amine
CAS Number	61-53-0 Y
PubChem CID	6092
ChemSpider	5867 Y
UNII	M6X6KY3BQH
CompTox Dashboard (EPA)	DTXSID90209848
Chemical and physical data
Formula	C12H16N2
Molar mass	188.274 g·mol−1
3D model (JSmol)	Interactive image
Melting point	87 to 88 °C (189 to 190 °F)
SMILES CCNCCc1c[nH]c2ccccc12
InChI 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 Y Key:TZWUSTVNAVKAPA-UHFFFAOYSA-N Y
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Use and effects

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

Pharmacodynamics

NMT activities

Target	Affinity (Ki, nM)
5-HT1A	IA
5-HT2A	38 (EC50Tooltip half-maximal effective concentration) 99% (EmaxTooltip maximal efficacy)
SERT	19a (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-HT_2A receptor full agonist and a selective serotonin releasing agent.^[2] It is inactive at the 5-HT_1A receptor.^[2]

Chemistry

Synthesis

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

Analogues

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

See also

• Substituted tryptamine