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Revision as of 11:15, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 464218644 of page N-Methyltryptamine for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 09:14, 2 November 2024 edit 76.174.0.57 (talk) Cat. 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{DISPLAYTITLE:''N''-Methyltryptamine}}
{{Drugbox
{{Infobox drug
| Verifiedfields = changed
| Verifiedfields = verified
| verifiedrevid = 462257424
| Watchedfields = verified
| IUPAC_name = 2-(1H-Indol-3-yl)-''N''-methylethanamine
| verifiedrevid = 464372446
| image = Methyltryptamine.png
| IUPAC_name = 2-(1''H''-Indol-3-yl)-''N''-methylethan-1-amine
| width = 140
| image = NMT structure.svg
| drug_name = ''N''-Methyltryptamine
| width =
| drug_name = ''N''-Methyltryptamine


<!--Clinical data--> <!--Clinical data-->| tradename = <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| tradename =
| legal_US = ]
| CAS_number = 61-49-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6FRL4L3Z7V
| PubChem = 6088
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5863
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C06213
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28136
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 348588
| synonyms = NMT; Methyltryptamine; ''N''-MT; Monomethyltryptamine; Dipterine


<!--Chemical data-->| C = 11
<!--Identifiers-->
| H = 14
| CAS_number_Ref = {{cascite|changed|??}}
| N = 2
| CAS_number = <!-- blanked - oldvalue: 61-49-4 -->
| smiles = CNCCc1cc2ccccc12
| PubChem = 6088
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3
| ChemSpiderID = 5863
| KEGG_Ref = {{keggcite|correct|kegg}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NCIKQJBVUNUXLW-UHFFFAOYSA-N
| KEGG = C06213
| melting_point = 87
| ChEBI_Ref = {{ebicite|correct|EBI}}
| melting_high = 89
| ChEBI = 28136
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 348588

<!--Chemical data-->
| C=11 | H=14 | N=2
| molecular_weight = 174.245 g/mol
| smiles = c1cccc2c1c(cn2)CCNC
| InChI = 1/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3
| InChIKey = NCIKQJBVUNUXLW-UHFFFAOYAC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NCIKQJBVUNUXLW-UHFFFAOYSA-N
| melting_point = 87
| melting_high = 89
}} }}

'''''N''-Methyltryptamine''' ('''NMT'''), also known as '''monomethyltryptamine''', is a ] of the ] family and a ] compound found in the human body and certain plants.

It is ] in humans from ] by certain ] ]s, such as ].<ref name="Renaissance GPCR">{{cite journal | vauthors = Lindemann L, Hoener MC | title = A renaissance in trace amines inspired by a novel GPCR family | journal = Trends in Pharmacological Sciences | volume = 26 | issue = 5 | pages = 274–281 | date = May 2005 | pmid = 15860375 | doi = 10.1016/j.tips.2005.03.007 }}</ref><ref name="Burchett">{{cite journal | vauthors = Burchett SA, Hicks TP | title = The mysterious trace amines: protean neuromodulators of synaptic transmission in mammalian brain | journal = Progress in Neurobiology | volume = 79 | issue = 5–6 | pages = 223–246 | date = August 2006 | pmid = 16962229 | doi = 10.1016/j.pneurobio.2006.07.003 | s2cid = 10272684 }}</ref> It is a known component in human urine.<ref name="pmid11763413">{{cite journal | vauthors = Forsström T, Tuominen J, Karkkäinen J | title = Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS | journal = Scandinavian Journal of Clinical and Laboratory Investigation | volume = 61 | issue = 7 | pages = 547–56 | date = 2001 | pmid = 11763413 | doi = 10.1080/003655101753218319 | s2cid = 218987277 }}</ref> NMT is an ] derived from ] that has been found in the ], ]s and ] of several plant ], including '']'', '']'', '']'', and '']''—often together with the related ]s ] (DMT) and ] (5-MeO-DMT).<ref> Ott, J. Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History (1993), ISBN 0-9614234-2-0 </ref>

NMT acts as a ] and ]<ref name="BloughLandavazoDecker2014" /> and produces ] and ]ic effects in humans.<ref name="TiHKAL1997" />

==Effects==
] NMT appears to produce no ] effects, likely as a result of extensive ].<ref name="ReferenceA">{{cite book | vauthors = Foye WO, Lemke TL, Williams DA | chapter = Hallucinogens, Stimulatants, and Drugs of Abuse | title = Foye's Principles of Medicinal Chemistry | date = 2002 | edition = 5th | isbn = 9780683307375| page = 439 | chapter-url = https://books.google.com/books?id=qLJ6Bs1Qml4C&q=NMT&pg=PA439}}</ref> However, it may become ] upon ] with a ] (MAOI).<ref name="ReferenceA"/>

By vaporization, NMT shows psychoactive activity at 50 to 100&nbsp;mg, with a ] of 45 to 70{{nbsp}}minutes; duration of visual effects is said to be only 15 to 30 seconds. Effects are primarily non-visual.<ref name="TiHKAL1997">{{cite book | vauthors = Shulgin A, Shulgin A | title = TiHKAL | date = 1997 | publisher = Transform Press | location = Berkeley }}</ref><ref>Nen - lecture presented EGA conference, Victoria, Australia 4/12/2011; and Breaking Conventions, London 12/7/2013.</ref>

==Pharmacology==
NMT is known to act as a ] ] ] ] ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} = 50.7{{nbsp}}nM; {{Abbrlink|E<sub>max</sub>|maximal efficacy}} = 96%).<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 has been reported to be inactive in activating the ] pathway of the receptor and hence appears to be a ] of the serotonin 5-HT<sub>2A</sub> receptor.<ref name="BloughLandavazoDecker2014" /> In contrast to the serotonin 5-HT<sub>2A</sub> receptor, the drug is not an agonist of the serotonin ].<ref name="BloughLandavazoDecker2014" />

In addition to its serotonin 5-HT<sub>2A</sub> receptor agonism, NMT is a potent ] ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} = 22.4{{nbsp}}nM).<ref name="BloughLandavazoDecker2014" /> It also releases ] and ] much more weakly ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} = 321{{nbsp}}nM and 733{{nbsp}}nM, respectively; 14- and 33-fold less than for serotonin, respectively).<ref name="BloughLandavazoDecker2014" />

== Legality ==
In the United States NMT is considered a schedule 1 controlled substance as an positional isomer of ] (AMT) <ref>{{Cite web |date=August 2023 |title=Orange Book - List of Controlled Substances and Regulated Chemicals |url=https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf |url-status=live |archive-url=https://web.archive.org/web/20230906002106/https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf |archive-date=September 6, 2023 |website=] Diversion Control Division}}</ref>

== See also ==
* ] (NET)
* ] (DMT)
* '']'' (a natural source of NMT, with other tryptamines, 1.63%. Buchanan et al. 2007)
* '']'' (NMT up to 2/3 alkaloid content)
* '']'' (synon. A. simplex) (1.44% NMT in bark, 0.29% twigs, Pouet ''et al.'' 1976)
* '']'' (NMT major component seasonally)

== References ==
{{Reflist}}

== External links ==
*
*

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

{{DEFAULTSORT:Methyltryptamine, N-}}

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