DMMDA-2

{{short description|Bioactive phenylethylamine}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477210401

| Name = DMMDA-2

| ImageFile = DMMDA-2.svg

| ImageSize =

| ImageName =

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

|Section1={{Chembox Identifiers

| InChI = 1/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

| InChIKey = UQXNREZPUUGSKM-UHFFFAOYAC

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

| ChEMBL = 424156

| PubChem = 16766527

| 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

| CASNo_Ref = {{cascite|correct|chemspider}}

| CASNo = 15183-26-3

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

| UNII = EPG4XUJ647

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

| ChemSpiderID =21106292

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

}}

|Section2={{Chembox Properties

| Formula = C₁₂H₁₇NO₄

| MolarMass = 239.27 g/mol

| MeltingPtC = 178 to 180

| MeltingPt_notes =

}}

}}

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 3,4-methylenedioxy-1-α-methylphenylethylamine. 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}}