MDMAI
Chemical compound
title: "MDMAI" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["2-aminoindanes", "david-e.-nichols", "designer-drugs", "entactogens", "methylenedioxyphenethylamines", "serotonin-releasing-agents"] description: "Chemical compound" topic_path: "general/2-aminoindanes" source: "https://en.wikipedia.org/wiki/MDMAI" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::summary Chemical compound ::
| Verifiedfields = changed | verifiedrevid = 477223870 | drug_name = | image = MDMAI.svg | image_class = skin-invert-image | alt = Structural formula of MDMAI | width = 250px | image2 = MDMAI 3D ball.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model of the MDMAI molecule | width2 = 250px
| tradename = | pregnancy_category = | routes_of_administration = | class = Serotonin releasing agent; Entactogen | ATC_prefix = None | ATC_suffix =
| legal_DE = NpSG | legal_UK = PSA | legal_status =
| bioavailability = | protein_bound = | metabolism = | onset = | elimination_half-life = | duration_of_action = | excretion =
| CAS_number_Ref = | CAS_number = 132741-82-3 | PubChem = 125559 | ChemSpiderID_Ref = | ChemSpiderID = 111695 | UNII_Ref = | UNII = 5N88M9ZTD8 | synonyms = 5,6-Methylenedioxy-N-methyl-2-aminoindane; MDMAI
| IUPAC_name = N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine | C=11 | H=13 | N=1 | O=2 | SMILES = C3c2cc1OCOc1cc2CC3NC | StdInChI_Ref = | 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 = | StdInChIKey = KNZKMFXEUONVMF-UHFFFAOYSA-N
MDMAI, also known as 5,6-methylenedioxy-N-methyl-2-aminoindane, is a drug of the 2-aminoindane family developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic serotonin releasing agent (SRA) in animals and is a putative entactogen in humans.
Interactions
History
MDMAI was first described in the scientific literature by David E. Nichols and colleagues in 1990.
Chemistry
MDMAI can be thought of as a cyclized analogue of MDMA where the α-methyl group of the alkylamino side chain has been joined back round to the 6-position of the aromatic ring to form an indane ring system. This changes the core structure of the molecule from phenethylamine to 2-aminoindane, and causes the pharmacological properties of the two compounds to be substantially different.
References
References
- (2011). "Aminoindanes--the next wave of 'legal highs'?". Drug Test Anal.
- (1990). "(+)-N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3,4-methylenedioxy-methamphetamine-like behavioral activity". J Pharmacol Exp Ther.
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