:DMMDA-2

{{Short description|Psychedelic drug}}

{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477210401

| drug_name =

| image = DMMDA-2.svg

| width = 200px

| caption =

| pronounce =

| tradename =

| Drugs.com =

| MedlinePlus =

| licence_CA =

| licence_EU =

| DailyMedID =

| licence_US =

| pregnancy_AU =

| pregnancy_category =

| dependency_liability =

| addiction_liability =

| routes_of_administration =

| class =

| ATC_prefix =

| ATC_suffix =

| legal_status =

| bioavailability =

| protein_bound =

| metabolism =

| metabolites =

| onset =

| elimination_half-life =

| duration_of_action =

| excretion =

| CAS_number_Ref = {{cascite|correct|chemspider}}

| CAS_number = 15183-26-3

| CAS_supplemental =

| PubChem = 16766527

| PubChemSubstance =

| IUPHAR_ligand =

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID =21106292

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

| UNII = EPG4XUJ647

| KEGG =

| ChEBI =

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 424156

| NIAID_ChemDB =

| PDB_ligand =

| synonyms =

| IUPAC_name = 1-(6,7-dimethoxy-2H-1,3-benzodioxol-5-yl)propan-2-amine

| C=12 | H=17 | N=1 | O=4

| SMILES = CC(N)Cc1cc2OCOc2c(OC)c1OC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C12H17NO4/c1-7(13)4-8-5-9-11(17-6-16-9)12(15-3)10(8)14-2/h5,7H,4,6,13H2,1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UQXNREZPUUGSKM-UHFFFAOYSA-N

| melting_point = 178

| melting_high = 180

}}

DMMDA-2 is a bioactive phenethylamine discussed by Alexander Shulgin in his book PiHKAL (Phenethylamines i Have Known And Loved); however, he was not the first to synthesize it.{{cite web |url=http://www.erowid.org/library/books_online/pihkal/pihkal059.shtml |title=#59 DMMDA-2|publisher= Erowid|work=PiHKAL: a chemical love story|access-date= 22 November 2011}} Shulgin comments in his book that a 50 milligram dose of DMMDA-2 produces similar effects to MDA. DMMDA-2 can be synthesized from dillapiole.

DMMDA-2 is equivalent to 5 mescaline units. DMMDA-2's isomer DMMDA is equivalent to 12 mescaline units.{{Cite journal | author = Clare, Brian W. | year = 1990 | title = Structure-Activity Correlations for Psychotomimetics. 1. Phenylalkylamines: Electronic, Volume, and Hydrophobicity Parameters | journal = Journal of Medicinal Chemistry | volume = 33 | issue = 7 | pages = 687–702 | url = https://www.erowid.org/archive/rhodium/pdf/sar.psychotomimetics-1.pdf | access-date = 2025-01-07}}