View source for N-Ethyltryptamine

{{Short description|Chemical compound}}
{{DISPLAYTITLE:''N''-Ethyltryptamine}}
{{Drugbox
| verifiedrevid = 447115197
| drug_name = ''N''-Ethyltryptamine
| image = N-Ethyltryptamine.png
| image_class = skin-invert-image
| width = 200px
| image2 = NET 3D.png
| image_class2 = bg-transparent
| width2 = 200px

<!--Clinical data-->
| tradename = 
| pregnancy_AU = 
| pregnancy_US = 
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| routes_of_administration = 
| ATC_prefix = None
| ATC_suffix = 

<!--Legal status-->
| legal_AU = 
| legal_CA = 
| legal_UK = 
| legal_US = [[List of Schedule I drugs|Schedule I (isomer of DMT)]]
| legal_status = 

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
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| elimination_half-life = 
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<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 61-53-0
| PubChem = 6092
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5867
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M6X6KY3BQH
| synonyms = NET; NETP; Ethyltryptamine

<!--Chemical data-->
| IUPAC_name = ''N''-ethyl-2-(1''H''-indol-3-yl)ethan-1-amine
| C=12 | H=16 | N=2 
| SMILES = CCNCCc1c[nH]c2ccccc12
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TZWUSTVNAVKAPA-UHFFFAOYSA-N

<!--Physical data-->
| melting_point = 87
| melting_high = 88
}}

'''''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>

==Use and effects==
[[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" />

==Pharmacology==
===Pharmacodynamics===
{| class="wikitable floatleft" style="font-size:small;"
|+ {{Nowrap|NMT activities}}
|-
! Target !! Affinity (K<sub>i</sub>, nM)
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || {{Abbr|IA|Inactive}}
|-
| [[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}})
|-
| [[Serotonin transporter|SERT]]|| 19<sup>a</sup> ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
|{{Abbrlink|NET|Norepinephrine transporter}}
|3,862<sup>a</sup> ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
|{{Abbrlink|DAT|Dopamine transporter}}
|6,660<sup>a</sup> ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|- class="sortbottom"
| 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" />'''
|}

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" /> 

==Chemistry==
===Synthesis===
The [[chemical synthesis]] of NET has been described.<ref name="TiHKAL" />

===Analogues===
[[Structural analog|Analogue]]s of NET include [[N-methyltryptamine|''N''-methyltryptamine]] (NMT), [[dimethyltryptamine]] (DMT), [[methylethyltryptamine]] (MET), and [[diethyltryptamine]] (DET), among others.<ref name="TiHKAL" />

==See also==
* [[Substituted tryptamine]]

==References==
{{Reflist}}

==External links==
* [https://isomerdesign.com/pihkal/explore/5049 NET - Isomer Design]

{{Serotonin receptor modulators}}
{{Monoamine releasing agents}}
{{Tryptamines}}

{{DEFAULTSORT:Ethyltryptamine, N-}}

[[Category:5-HT2A agonists]]
[[Category:N-Monoalkyltryptamines]]
[[Category:Serotonin receptor agonists]]
[[Category:Serotonin releasing agents]]