Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and N-Methyltryptamine: Difference between pages

{{Short description|Chemical compound}}

{{DISPLAYTITLE:''N''-Methyltryptamine}}

{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464372446

| IUPAC_name = 2-(1''H''-Indol-3-yl)-''N''-methylethan-1-amine

| image = NMT structure.svg

| width =

| drug_name = ''N''-Methyltryptamine

<!--Clinical data-->| tradename = <!--Identifiers-->

| CAS_number_Ref = {{cascite|changed|??}}

| legal_US = [[List of Schedule I drugs|Schedule I (isomer of AMT)]]

| 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

<!--Chemical data-->| C = 11

| H = 14

| N = 2

| smiles = CNCCc1c[nH]c2ccccc12

| 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''') is a member of the [[substituted tryptamine]] [[chemical class]] and a [[natural product]] which is [[biosynthesized]] in the human body from [[tryptamine]] by certain [[N-methyltransferase]] [[enzyme]]s, such as [[indolethylamine N-methyltransferase|indolethylamine ''N''-methyltransferase]].<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 common 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 [[alkaloid]] derived from [[tryptophan|<small>L</small>-tryptophan]] that has been found in the [[tree bark|bark]], [[Shoot (botany)|shoot]]s and [[leaf|leaves]] of several plant [[Genus|genera]], including ''[[Virola]]'', ''[[Acacia]]'', ''[[Mimosa]]'', and ''[[Desmanthus]]''—often together with the related [[chemical compound|compound]]s [[N,N-dimethyltryptamine|''N'',''N''-dimethyltryptamine]] (DMT) and [[5-methoxy-N,N-dimethyltryptamine|5-methoxy-''N'',''N''-dimethyltryptamine]] (5-MeO-DMT).{{citation needed|date=August 2015}}

Orally administered NMT appears to produce no [[psychoactive]] effects, likely as a result of extensive [[first-pass metabolism]].<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 [[bioactivity|active]] upon [[Augmentation (psychiatry)|combination]] with a [[monoamine oxidase inhibitor|MAO_A inhibitor]] (MAOI).<ref name="ReferenceA"/>

By vaporization NMT shows activity at 50–100&nbsp;mg, with a duration of 45–70 minutes; duration of visual effects 15–30 seconds. Effects are primarily non-visual.<ref>{{cite book | vauthors = Shulgin A, Shulgin A | title = TIKHAL | 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>

== Legality ==

In the United States N-Methyltryptamine is considered a schedule 1 controlled substance as an positional isomer of [[Alpha-methyltryptamine]] (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=[[U.S. Department of Justice]] Diversion Control Division}}</ref>

== See also ==

* [[N-Ethyltryptamine|''N''-Ethyltryptamine]] (NET)

* [[N,N-Dimethyltryptamine|''N'',''N'',-Dimethyltryptamine]] (DMT)

* ''[[Acacia confusa]]'' (a natural source of NMT, with other tryptamines, 1.63%. Buchanan et al. 2007)

* ''[[Acacia obtusifolia]]'' (NMT up to 2/3 alkaloid content)

* ''[[Acacia simplicifolia]]'' (synon. A. simplex) (1.44% NMT in bark, 0.29% twigs, Pouet ''et al.'' 1976)

* ''[[Desmanthus illinoensis]]'' (NMT major component seasonally)

== References ==

{{Reflist}}

== External links ==

* [http://www.erowid.org/library/books_online/tihkal/tihkal50.shtml NMT Entry in ''TIHKAL'']

* [http://tihkal.info/read.php?domain=tk&id=50 NMT Entry in TiHKAL • info]

{{Neurotransmitters}}

{{Hallucinogens}}

{{Serotonergics}}

{{Tryptamines}}

{{DEFAULTSORT:Methyltryptamine, N-}}

[[Category:Tryptamine alkaloids]]

[[Category:Psychedelic tryptamines]]

[[Category:Serotonin receptor agonists]]