MDAI

MDAI
Clinical data
Other names5,6-Methylenedioxy-2-aminoindane; 5,6-Methylenedioxy-2-aminoindan; Methylenedioxyaminoindane; Methylenedioxyaminoindan
Routes of
administration		Oral[1]
Drug classSerotonin–norepinephrine releasing agent;[2] Entactogen[1]
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action2–6 hours[4][1]
Identifiers
IUPAC name
  • 6,7-Dihydro-5H-cyclopenta[f] [1,3]benzodioxol-6-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H11NO2
Molar mass177.203 g·mol−1
3D model (JSmol)
SMILES
  • C1C(CC2=CC3=C(C=C21)OCO3)N
InChI
  • InChI=1S/C10H11NO2/c11-8-1-6-3-9-10(13-5-12-9)4-7(6)2-8/h3-4,8H,1-2,5,11H2 Y
  • Key:FQDRMHHCWZAXJM-UHFFFAOYSA-N Y

MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen drug of the 2-aminoindane group which is related to MDMA and produces similar subjective effects.[4][5][6][1]

It acts as a selective serotonin and norepinephrine releasing agent (SNRA).[2] The drug shows greatly reduced serotonergic neurotoxicity in comparison to MDMA in animals, although it still shows weak capacity for neurotoxicity with chronic use or in combination with amphetamine.[7][8][9]

MDAI was developed in the 1990s by a team led by David E. Nichols at Purdue University.[10] It has been encountered as a designer drug and has been used recreationally with reported street names such as "sparkle" and "mindy".[5][11][7][6] In addition to its recreational use, there has been interest in MDAI for potential use in medicine, for instance in drug-assisted psychotherapy.[4]

  1. ^ a b c d Cite error: The named reference AngererSchmidFranz2024 was invoked but never defined (see the help page).
  2. ^ a b Cite error: The named reference HalberstadtBrandtWalther2019 was invoked but never defined (see the help page).
  3. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  4. ^ a b c Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". Journal of Psychopharmacology. 35 (5). SAGE Publications: 512–536. doi:10.1177/0269881120920420. PMC 8155739. PMID 32909493.
  5. ^ a b Pinterova N, Horsley RR, Palenicek T (17 November 2017). "Synthetic Aminoindanes: A Summary of Existing Knowledge". Frontiers in Psychiatry. 8. Frontiers Media SA: 236. doi:10.3389/fpsyt.2017.00236. PMC 5698283. PMID 29204127.
  6. ^ a b Sainsbury PD, Kicman AT, Archer RP, King LA, Braithwaite RA (2011). "Aminoindanes--the next wave of 'legal highs'?". Drug Testing and Analysis. 3 (7–8). Wiley: 479–482. doi:10.1002/dta.318. PMID 21748859.
  7. ^ a b Cite error: The named reference CorkeryElliottSchifano2013 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference NicholsMarona-LewickaHuang1993 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference JohnsonHuangNichols1991 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference JohnsonConartyNichols1991 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference GallagherAssiStair2012 was invoked but never defined (see the help page).
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