MDMAI

{{short description|Chemical compound}}

{{one source|date=October 2014}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 477223870

| IUPAC_name = N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine

| image = MDMAI.svg

| alt = Structural formula of MDMAI

| image2 = MDMAI 3D ball.png

| alt2 = Ball-and-stick model of the MDMAI molecule

| width2 = 250

| drug_name = 5,6-Methylenedioxy-N-methyl-2-aminoindane

| tradename =

| pregnancy_category =

| legal_DE = NpSG

| legal_UK = PSA

| legal_status =

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 132741-82-3

| ATC_prefix = none

| ATC_suffix =

| PubChem = 125559

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

| ChemSpiderID = 111695

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

| UNII = 5N88M9ZTD8

| C=11 | H=13 | N=1 | O=2

| smiles = C3c2cc1OCOc1cc2CC3NC

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

| StdInChI = 1S/C11H13NO2/c1-12-9-2-7-4-10-11(14-6-13-10)5-8(7)3-9/h4-5,9,12H,2-3,6H2,1H3

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

| StdInChIKey = KNZKMFXEUONVMF-UHFFFAOYSA-N

}}

5,6-Methylenedioxy-N-methyl-2-aminoindane (MDMAI), is a drug of the 2-aminoindane group developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) in animals and a putative entactogen in humans.{{cite journal | vauthors = Oberlender R, Nichols DE | title = (+)-N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3,4-methylenedioxy-methamphetamine-like behavioral activity| journal = J Pharmacol Exp Ther | volume = 255 | issue = 3 | pages = 1098–1106 | year = 1990 | pmid = 1979813 }}