Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 3-Methoxy-4-methylamphetamine: Difference between pages

{{Short description|Entactogen and psychedelic drug of the phenethylamine and amphetamine classes}}

| Verifiedfields = changed

| verifiedrevid = 477219322

| legal_DE = NpSG

| legal_UK = Class A

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

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 24160-29-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = BHS67KQE5Q

'''3-Methoxy-4-methylamphetamine''' ('''MMA''') is an [[entactogen]] and [[psychedelic drug|psychedelic]] [[drug]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted amphetamine|amphetamine]] classes.<ref name="HoMcIsaacAn1970">{{cite journal | vauthors = Ho BT, McIsaac WM, An R, Tansey LW, Walker KE, Englert LF, Noel MB | title = Analogs of alpha-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs | journal = Journal of Medicinal Chemistry | volume = 13 | issue = 1 | pages = 26–30 | date = January 1970 | pmid = 5412110 | doi = 10.1021/jm00295a007 }}</ref><ref name="JohnsonFrescasOberlender1991">{{cite journal | vauthors = Johnson MP, Frescas SP, Oberlender R, Nichols DE | title = Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA) | journal = Journal of Medicinal Chemistry | volume = 34 | issue = 5 | pages = 1662–1668 | date = May 1991 | pmid = 1674539 | doi = 10.1021/jm00109a020 }}</ref> It was first [[Organic synthesis|synthesized]] in 1970<ref name="HoMcIsaacAn1970" /> and was encountered as a [[street drug]] in [[Italy]] in the same decade.<ref>{{cite journal | vauthors = de Zorzi C, Cavalli A | title = Un nuovo allucinogeno: la MMA (p-metil-m-metossi anfetamina) | trans-title = A new hallucinogen: MMA (p-methyl-m-methoxy amphetamine) | language = Italian | journal = Zacchia | date = 1974 | volume = 49 | issue = 1 | pages = 58–68 }}</ref> MMA was largely forgotten until being reassayed by [[David E. Nichols]] as a non-[[neurotoxic]] [[MDMA]] [[structural analog|analogue]] in 1991,<ref name="JohnsonFrescasOberlender1991" /> and has subsequently been sold as a [[designer drug]] on the internet since the late 2000s.{{Citation needed|date=December 2024}}

In animal studies, MMA fully substitutes for [[MDMA]] and [[MBDB]], partially substitutes for [[LSD]], and does not substitute for [[amphetamine]].<ref name="JohnsonFrescasOberlender1991" /> Additionally, it has been shown to be a [[potency (pharmacology)|potent]] and highly [[binding selectivity|selective]] [[serotonin releasing agent]] (SSRA) and does not produce [[Serotonin|serotonergic]] [[neurotoxicity]] in rodents.<ref name="JohnsonConartyNichols1991">{{cite journal | vauthors = Johnson MP, Conarty PF, Nichols DE | title = [3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues | journal = Eur J Pharmacol | volume = 200 | issue = 1 | pages = 9–16 | date = July 1991 | pmid = 1685125 | doi = 10.1016/0014-2999(91)90659-e | url = }}</ref><ref name="JohnsonFrescasOberlender1991" /><ref name="RudnickWall1993">{{cite journal | vauthors = Rudnick G, Wall SC | title = Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters | journal = Mol Pharmacol | volume = 43 | issue = 2 | pages = 271–276 | date = February 1993 | pmid = 8429828 | doi = | url = }}</ref> These data appear to confer a profile of MMA as a [[selective serotonin releasing agent]] (SSRA) and [[serotonin]] [[5-HT2A receptor|5-HT_2A receptor]] [[agonist]].<ref name="JohnsonFrescasOberlender1991" />

In humans, MMA has been reported to be [[hallucinogen]]ic, "quite [[dysphoria|dypshoric]]", and long-lasting.<ref name="ShulginShulgin1991">{{cite book | vauthors = Shulgin A, Shulgin A | title = Pihkal: A Chemical Love Story | publisher = Transform Press | year = 1991 | isbn = 0-9630096-0-5 | url = http://www.erowid.org/library/books_online/pihkal/pihkal123.shtml | quote = Some years ago a report appeared in the forensic literature of Italy, of the seizure of a small semi-transparent capsule containing 141 milligrams of a white powder that was stated to be a new hallucinogenic drug. This was shown to contain an analogue of DOM, 3-methoxy-4-methylamphetamine, or MMA. The Italian authorities made no mention of the net weight contained in each dosage unit, but it has been found that the active level of MMA in man is in the area of 40-60 milligrams. The compound can apparently be quite dysphoric, and long lived.}}</ref> The active doses have been reported to be 40 to 60{{nbsp}}mg.<ref name="ShulginShulgin1991" /> [[Capsule (pharmacy)|Capsule]]s containing 140{{nbsp}}mg have been encountered as a designer drug in [[Italy]] in the 1980s.<ref name="ShulginShulgin1991" />

== See also ==

* [[3-Methoxyamphetamine]] (3-MeOA)

* [[3-Methoxymethamphetamine]] (MMMA)

* [[4-Methylamphetamine]] (4-MA)

* [[4-Methylmethamphetamine]] (4-MMA)

* [[4-Methylmethcathinone]] (4-MMC)

* [[4-Cl-3-MMC]]

== References ==

{{Reflist}}

{{Entactogens}}

{{Hallucinogens}}

{{Monoamine releasing agents}}

{{Serotonin receptor modulators}}

{{Phenethylamines}}

{{DEFAULTSORT:Methoxy-4-methylamphetamine, 3-}}

[[Category:Designer drugs]]

[[Category:Entactogens and empathogens]]

[[Category:Phenol ethers]]

[[Category:Serotonin receptor agonists]]

[[Category:Serotonin releasing agents]]

[[Category:Substances discovered in the 1970s]]

[[Category:Substituted amphetamines]]