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N-Ethyltryptamine - Revision history
2026-08-05T04:37:23Z
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2025-11-18T02:28:54Z
<p>Fix.</p>
<p><b>New page</b></p><div>{{Short description|Chemical compound}}<br />
{{DISPLAYTITLE:''N''-Ethyltryptamine}}<br />
{{Drugbox<br />
| verifiedrevid = 447115197<br />
| drug_name = ''N''-Ethyltryptamine<br />
| image = N-Ethyltryptamine.png<br />
| image_class = skin-invert-image<br />
| width = 200px<br />
| image2 = NET 3D.png<br />
| image_class2 = bg-transparent<br />
| width2 = 200px<br />
<br />
<!--Clinical data--><br />
| tradename = <br />
| pregnancy_AU = <br />
| pregnancy_US = <br />
| pregnancy_category = <br />
| routes_of_administration = <br />
| ATC_prefix = None<br />
| ATC_suffix = <br />
<br />
<!--Legal status--><br />
| legal_AU = <br />
| legal_CA = <br />
| legal_UK = <br />
| legal_US = [[List of Schedule I drugs|Schedule I (isomer of DMT)]]<br />
| legal_status = <br />
<br />
<!--Pharmacokinetic data--><br />
| bioavailability = <br />
| protein_bound = <br />
| metabolism = <br />
| elimination_half-life = <br />
| excretion = <br />
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<!--Identifiers--><br />
| CAS_number_Ref = {{cascite|correct|??}}<br />
| CAS_number = 61-53-0<br />
| PubChem = 6092<br />
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}<br />
| ChemSpiderID = 5867<br />
| UNII_Ref = {{fdacite|correct|FDA}}<br />
| UNII = M6X6KY3BQH<br />
| synonyms = NET; NETP; Ethyltryptamine<br />
<br />
<!--Chemical data--><br />
| IUPAC_name = ''N''-ethyl-2-(1''H''-indol-3-yl)ethan-1-amine<br />
| C=12 | H=16 | N=2 <br />
| SMILES = CCNCCc1c[nH]c2ccccc12<br />
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}<br />
| StdInChI = 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<br />
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}<br />
| StdInChIKey = TZWUSTVNAVKAPA-UHFFFAOYSA-N<br />
<br />
<!--Physical data--><br />
| melting_point = 87<br />
| melting_high = 88<br />
}}<br />
<br />
'''''N''-Ethyltryptamine''' ('''NET'''), also abbreviated as NETP, is a [[substituted tryptamine|tryptamine]] that is [[structural analog|structurally related]] to [[N-methyltryptamine|''N''-methyltryptamine]] (NMT) and the [[psychedelic drug]]s [[N,N-dimethyltryptamine|''N'',''N''-dimethyltryptamine]] (DMT) and [[diethyltryptamine|''N'',''N''-diethyltryptamine]] (DET).<ref name="TiHKAL">[http://www.erowid.org/library/books_online/tihkal/tihkal49.shtml NET Entry in ''TIHKAL'']</ref><br />
<br />
==Use and effects==<br />
[[Alexander Shulgin]] included NET as an entry in his book ''[[TiHKAL]]'' (''Tryptamines I Have Known and Loved'').<ref name="TiHKAL" /> However, he stated that it had been subjected only to modest human trials and that no active dose level had been identified.<ref name="TiHKAL" /><br />
<br />
==Pharmacology==<br />
===Pharmacodynamics===<br />
{| class="wikitable floatleft" style="font-size:small;"<br />
|+ {{Nowrap|NMT activities}}<br />
|-<br />
! Target !! Affinity (K<sub>i</sub>, nM)<br />
|-<br />
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || {{Abbr|IA|Inactive}}<br />
|-<br />
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 38 ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}})<br />99% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}})<br />
|-<br />
| [[Serotonin transporter|SERT]]|| 19<sup>a</sup> ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />
|-<br />
|{{Abbrlink|NET|Norepinephrine transporter}}<br />
|3,862<sup>a</sup> ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />
|-<br />
|{{Abbrlink|DAT|Dopamine transporter}}<br />
|6,660<sup>a</sup> ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />
|- class="sortbottom"<br />
| colspan="2" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug interacts with the site. '''Footnotes:''' <sup>a</sup> = [[Monoamine releasing agent|Neurotransmitter release]]. '''Sources: <ref name="BloughLandavazoDecker2014" />'''<br />
|}<br />
<br />
NET has been found to act as a [[potency (pharmacology)|potent]] [[serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] [[full agonist]] and a selective [[serotonin releasing agent]].<ref name="BloughLandavazoDecker2014">{{cite journal | vauthors = Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB | title = Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes | journal = Psychopharmacology (Berl) | volume = 231 | issue = 21 | pages = 4135–4144 | date = October 2014 | pmid = 24800892 | pmc = 4194234 | doi = 10.1007/s00213-014-3557-7 | url = }}</ref> It is inactive at the [[5-HT1A receptor|5-HT<sub>1A</sub> receptor]].<ref name="BloughLandavazoDecker2014" /> <br />
<br />
==Chemistry==<br />
===Synthesis===<br />
The [[chemical synthesis]] of NET has been described.<ref name="TiHKAL" /><br />
<br />
===Analogues===<br />
[[Structural analog|Analogue]]s of NET include [[N-methyltryptamine|''N''-methyltryptamine]] (NMT), [[dimethyltryptamine]] (DMT), [[methylethyltryptamine]] (MET), and [[diethyltryptamine]] (DET), among others.<ref name="TiHKAL" /><br />
<br />
==See also==<br />
* [[Substituted tryptamine]]<br />
<br />
==References==<br />
{{Reflist}}<br />
<br />
==External links==<br />
* [https://isomerdesign.com/pihkal/explore/5049 NET - Isomer Design]<br />
<br />
{{Serotonin receptor modulators}}<br />
{{Monoamine releasing agents}}<br />
{{Tryptamines}}<br />
<br />
{{DEFAULTSORT:Ethyltryptamine, N-}}<br />
<br />
[[Category:5-HT2A agonists]]<br />
[[Category:N-Monoalkyltryptamines]]<br />
[[Category:Serotonin receptor agonists]]<br />
[[Category:Serotonin releasing agents]]</div>
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