MMDA-2

{{short description|Psychedelic drug}}

{{Drugbox

| IUPAC_name = 1-(6-Methoxy-1,3-benzodioxol-5-yl)propan-2-amine

| image = MMDA-2.svg

| tradename =

| pregnancy_category =

| legal_CA = Schedule I

| legal_DE = NpSG

| legal_UK = Class A

| legal_status = Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)

| routes_of_administration = Oral, Insufflated, Rectal

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 23693-18-7

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

| UNII = TG0B6ER184

| ATC_prefix = none

| ATC_suffix =

| PubChem = 90966

| ChemSpiderID = 82147

| synonyms = 2-Methoxy-4,5-methylenedioxyamphetamine; 6-Methoxy-MDA; 6-MeO-MDA

| C=11 | H=15 | N=1 | O=3

| smiles = O1c2cc(c(OC)cc2OC1)CC(N)C

}}

MMDA-2, also known as 2-methoxy-4,5-methylenedioxyamphetamine or as 6-methoxy-MDA, is a psychedelic drug of the amphetamine class.{{cite book | vauthors = Shulgin A, Shulgin A | chapter = MMDA-2 (2-Methoxy-4,5-methylenedioxyamphetamine) | title = Pihkal: A Chemical Love Story | publisher = Transform Press | date = 13 May 2016 | isbn = 978-0-9630096-0-9 | chapter-url = http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=133 }} It is closely related to MMDA and MDA.

Alexander Shulgin was likely the first to synthesize MMDA-2. In his book PiHKAL, the dose is listed as 25–50 mg, and the duration is listed as 8–12 hours. Shulgin reports that MMDA-2 produces effects such as enhanced awareness, empathy, and visual facilitation and distortion, as well as some side effects like gastrointestinal upset and appetite loss. He states that 30 mg is very similar to 80 mg of MDA, and also remarks that it would be impossible for anyone to have a bad experience on the drug at that dose.

Scientific research has shown that MMDA-2, unlike MMDA, but similarly to 6-methyl-MDA, is only very weak at inducing the release of serotonin or dopamine,{{cite journal | vauthors = McKenna DJ, Guan XM, Shulgin AT | title = 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine | journal = Pharmacology, Biochemistry, and Behavior | volume = 38 | issue = 3 | pages = 505–512 | date = March 1991 | pmid = 1829838 | doi = 10.1016/0091-3057(91)90005-M | s2cid = 2740262 | doi-access = free }} and accordingly, does not produce amphetamine-like responses in animals in drug discrimination studies.{{cite journal | vauthors = Glennon RA, Yousif M, Naiman N, Kalix P | title = Methcathinone: a new and potent amphetamine-like agent | journal = Pharmacology, Biochemistry, and Behavior | volume = 26 | issue = 3 | pages = 547–551 | date = March 1987 | pmid = 3575369 | doi = 10.1016/0091-3057(87)90164-X | s2cid = 5890314 }} Instead, MMDA-2 is likely to act as a pure serotonin 5-HT₂ receptor agonist similarly to the DOx series of compounds, with activation of the serotonin 5-HT_2A receptor conferring its psychedelic effects.{{cite journal | vauthors = Clare BW | title = QSAR of benzene derivatives: comparison of classical descriptors, quantum theoretic parameters and flip regression, exemplified by phenylalkylamine hallucinogens | journal = Journal of Computer-Aided Molecular Design | volume = 16 | issue = 8–9 | pages = 611–633 | year = 2002 | pmid = 12602954 | doi = 10.1023/A:1021966231380 | s2cid = 9948738 | bibcode = 2002JCAMD..16..611C }}

MMDA-2 has been sold as a designer drug in Japan.{{cite journal | vauthors = Min JZ, Shimizu Y, Toyo'oka T, Inagaki S, Kikura-Hanajiri R, Goda Y | title = Simultaneous determination of 11 designated hallucinogenic phenethylamines by ultra-fast liquid chromatography with fluorescence detection | journal = Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences | volume = 873 | issue = 2 | pages = 187–194 | date = October 2008 | pmid = 18789774 | doi = 10.1016/j.jchromb.2008.08.020 }}