{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = | image = Methyl-TMA.svg | image_class = skin-invert-image | width = 225px | caption =
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="PiHKAL" /> | class = Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =
<!-- Identifiers --> | CAS_number = 93675-34-4 | CAS_supplemental = | PubChem = 24257271 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 23900079 | UNII = | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = METHYL-TMA; ''N''-Me-TMA; ''N''-Methyl-TMA; α,''N''-Dimethylmescaline; ''N''-Methyl-3,4,5-trimethoxyamphetamine
<!-- Chemical data --> | IUPAC_name = ''N''-methyl-1-(3,4,5-trimethoxyphenyl)propan-2-amine | C=13 | H=21 | N=1 | O=3 | SMILES = CC(CC1=CC(=C(C(=C1)OC)OC)OC)NC | StdInChI = 1S/C13H21NO3/c1-9(14-2)6-10-7-11(15-3)13(17-5)12(8-10)16-4/h7-9,14H,6H2,1-5H3 | StdInChIKey = XYKHBBWJSFSLRF-UHFFFAOYSA-N }}
'''Methyl-TMA''', or '''''N''-methyl-TMA''', also known as '''''N''-methyl-3,4,5-trimethoxyamphetamine''', is a psychedelic drug of the phenethylamine, amphetamine, and 3C families.<ref name="PiHKAL">{{CitePiHKAL }} "Three additional N-methylated homologues of known psychedelics warrant mention, but do not really deserve separate recipes. This is because they have had only the most cursory assaying, which I have learned about by personal correspondence. [...] METHYL-TMA [...] had been run up in several trials to a maximum of 240 [mg], with some mental disturbances mentioned only at this highest level. METHYL-TMA-2 [...] had been tried at up to 120 [mg] without any effects. METHYL-TMA-6 [...] had been tried at up to 30 [mg] and it, too, was apparently without effects. These are reports that I have heard from others, but I have had no personal experience with them. Those that I can describe from personal experience are entered separately as recipes of their own. And there are many, many other N-methyl homologues which have been prepared and characterized in the literature, and have yet to be tasted. So far, however, the only consistent thing seen is that, with N-methylation, the potency of the psychedelics is decreased, but the potency of the stimulants appears to be pretty much maintained."</ref><ref name="Shulgin_2011">{{cite book | vauthors = Shulgin A, Manning T, Daley P | title = The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | location = Berkeley | volume = 1 | pages = 288, 350, 383, 408 | year = 2011 | publisher = Transform Press | isbn = 978-0-9630096-3-0 }}</ref> It is the ''N''-methyl derivative of 3,4,5-trimethoxyamphetamine (TMA) as well as the α,''N''-dimethyl derivative of mescaline (3,4,5-trimethoxyphenethylamine).<ref name="PiHKAL" /><ref name="Shulgin_2011" />
== Use and effects == ''N''-Methylation of psychedelic phenethylamines has invariably greatly reduced or eliminated their hallucinogenic activity.<ref name="Nichols_2018">{{cite book | vauthors = Nichols DE | title = Chemistry and Structure-Activity Relationships of Psychedelics | volume = 36 | pages = 1–43 | date = 2018 | pmid = 28401524 | doi = 10.1007/7854_2017_475 | series = Current Topics in Behavioral Neurosciences | isbn = 978-3-662-55878-2 | url = https://bitnest.netfirms.com/external/10.1007/7854_2017_475 | quote = Although the most active tryptamine hallucinogens are N,N-dialkylated, the phenethylamines generally cannot tolerate even a single N-substitution. Even small groups such as methyl or ethyl (see Table 2) abolish their hallucinogenic activity. }}</ref><ref name="PiHKAL" /><ref name="Shulgin_1980">{{cite book | vauthors = Shulgin AT | veditors = Burger A, Wolf ME | chapter = Hallucinogens | title = Burger's Medicinal Chemistry | location = New York | volume = 3 | pages = 1109–1137 | date = 1980 | chapter-url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5 | edition = 4 | publisher = Wiley | isbn = 978-0-471-01572-7 | oclc = 219960627 | url = https://books.google.com/books?id=2b3wAAAAMAAJ | quote = Of all the variously substituted phenylisopropylamines that have been N-methylated and titrated in man (including the homologs of TMA-2, 2,5-DMA, DOM, and DOB: 60.22b, 60.22i, 60.22aa, and 60.22ff, respectively), it is only the methylenedioxy compound 60.23a that has maintained quantitative potency (94). As with mescaline itself, dimethylation of this compound eliminates any central action. }}</ref><ref name="Jacob_1994">{{cite book | vauthors = Jacob P, Shulgin AT | veditors = Lin GC, Glennon RA | chapter = Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs | title = Hallucinogens: An Update | volume = 146 | pages = 74–91 | date = 1994 | pmid = 8742795 | series = National Institute on Drug Abuse Research Monograph Series | publisher = National Institute on Drug Abuse | url = https://archives.nida.nih.gov/sites/default/files/monograph146.pdf | chapter-url = https://bibliography.maps.org/resources/download/11534 | archive-url = https://web.archive.org/web/20250713011914/https://bibliography.maps.org/resources/download/11534 | archive-date = 13 July 2025 | quote = [MDA] is also remarkable because the N-methyl homolog 3,4 (MDMA) has biological activity, although the nature of its action places it outside of this review. No other phenethylamine hallucinogen retains central activity on N-methylation. }}</ref> Examples of this include related compounds like Beatrice (''N''-methyl-DOM) and methyl-DOB (''N''-methyl-DOB), which at assessed doses appear to be inactive as psychedelics in humans.<ref name="Trachsel_2013">{{cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | title = Phenethylamine: von der Struktur zur Funktion | location = Solothurn | pages = 834–835, 878 | year = 2013 | trans-title = Phenethylamines: From Structure to Function | edition = 1 | publisher = Nachtschatten-Verlag | series = Nachtschatten-Science | isbn = 978-3-03788-700-4 | oclc = 858805226 | url = https://books.google.com/books?id=-Us1kgEACAAJ | language = de | quote = 8.5.26. N-Substitution von 2,4,5-trisubstituierten Phenylalkylaminen: Einerseits wurde der Einfluss von N-Alkyl-, andererseits derjenige von N-Heterogruppen-Substituenten geprüft. Allgemein ist bekannt, dass das Einführen von Alkylsubstituenten am Stickstoff von psychedelischen Phenylalkylaminen eine Abnahme der HT2-Rezeptoraffinitäten zur Folge hat [29, 150, 151]. Die Wirkungsabschwächung konnte mit den potenten Substanzen DOB (2) und DOM (8) im Menschen bestätigt werden [8]: N-Methyl-DOM (316; BEATRICE) und METHYL-DOB (317) erwiesen sich im Vergleich zu den beiden unmethylierten Verbindungen als massiv weniger aktiv; die aktive Dosis wurde dabei noch nicht eruiert. METHYL-DOET (318; DOETM) erwies sich bei einer Dosierung von 18mg bereits als deutlich aktiv [140]; die Wirkungen wurden im Vergleich zu DOET (14) als ruhiger und angenehmer beschrieben. [...] 318; METHYL-DOET, 18mg, 8-10h. [...] [140] P. Rausch. Persönliche Mitteilung, 2009. }}</ref><ref name="PiHKAL" /><ref name="Shulgin_1980" /><ref name="Jacob_1994" /> According to Alexander Shulgin in his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') however, methyl-TMA showed "some mental disturbances" at the highest assessed dose of 240{{nbsp}}mg orally.<ref name="PiHKAL" /> For comparison, the active dose range of TMA is 100 to 250{{nbsp}}mg orally.<ref name="PiHKAL" />
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
== History == Methyl-TMA was first described in the scientific literature by at least 1984.<ref name="Shulgin_2011" /><ref name="Clark_1984">{{cite journal | vauthors = Clark C | title = The Identification of Methoxy-N-Methylamphetamines | journal = Journal of Forensic Sciences | volume = 29 | issue = 4 | pages = 1056–1071 | date = 1 October 1984 | doi = 10.1520/JFS11772J | issn = 0022-1198 }}</ref> It was subsequently described further by Shulgin in ''PiHKAL'' in 1991.<ref name="PiHKAL" />
==Society and culture== ===Legal status=== ====Canada==== Methyl-TMA is a controlled substance in Canada under phenethylamine blanket-ban language.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>
==See also== * 3C (psychedelics) * ''N''-Methylmescaline * Trichocereine (''N'',''N''-dimethylmescaline) * Beatrice (''N''-methyl-DOM) * ''N''-Methyl-DOET * ''N''-Methyl-DOB * ''N''-Methyl-TMA-2 * Methyl-DMA (''N''-methyl-2,5-DMA)
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/288 METHYL-TMA - Isomer Design]
{{Psychedelics}} {{Phenethylamines}}
Category:3C (psychedelics) Category:Methamphetamines Category:Methoxy compounds Category:Psychedelic phenethylamines