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Names

5,6-MDAI
2-Amino-5,6-methylenedioxyindane
MDAI

IUPAC names

6,7-Dihydro-2H,5H-indeno[5,6-d][1,3]dioxol-6-amine
6,7-Dihydro-5H-indeno[5,6-d][1,3]dioxol-6-amine

ID 2149 · Formula C₁₀H₁₁NO₂ · Molecular weight 177.2

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

InChI Key FQDRMHHCWZAXJM-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES NC1Cc2c(C1)cc1c(c2)OCO1

ChemSpider 111694
PubChem 125558
Wikidata Q6715120
Erowid MDAI
Wikipedia: MDAI
Blotter MDAI
PsychonautWiki MDAI
Project Response 1597-16
Project Response 1347-15
swgdrug.org 5,6-Methylenedioxy-2-aminoindane (5,6-MDAI)
bluelight.org The Big & Dandy MDAI Thread: Second Dose

Shulgin Index See #77 MDA · Table 5Page 347Row 24

PiHKAL #100 MDA

Phenethylamine: Von der Strucktur zur Funktion 5,6-MDAI: 7.5 (99) 596

Johnson, MP; Frescas, SP; Oberlender, R; Nichols, DE. Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: Similarities to 3,4-(methylenedioxy)methamphetamine (MDMA). J. Med. Chem., 1 May 1991, 34 (5), 1662–1668. 975 kB. https://doi.org/10.1021/jm00109a020

Nichols, DE; Brewster, WK; Johnson, MP; Oberlender, R; Riggs, RM. Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA). J. Med. Chem., 1 Feb 1990, 33 (2), 703–710. 1.1 MB. https://doi.org/10.1021/jm00164a037

Johnson, MP; Conarty, PF; Nichols, DE. [³H]Monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues. Eur. J. Pharmacol., 23 Jul 1991, 200 (1), 9–16. 1.1 MB. https://doi.org/10.1016/0014-2999(91)90659-E

Oberlender, R; Nichols, DE. Structural variation and (+)-amphetamine-like discriminative stimulus properties. Pharmacol. Biochem. Behav., 1 Mar 1991, 38 (3), 581–586. 586 kB. https://doi.org/10.1016/0091-3057(91)90017-V

Johnson, MP; Huang, X; Nichols, DE. Serotonin neurotoxicity in rats after combined treatment with a dopaminergic agent followed by a nonneurotoxic 3,4-methylenedioxymethamphetamine (MDMA) analogue. Pharmacol. Biochem. Behav., 1 Dec 1991, 40 (4), 915–922. 845 kB. https://doi.org/10.1016/0091-3057(91)90106-C

Elie, L; Baron, M; Croxton, R; Elie, M. Microcrystalline identification of selected designer drugs. Forensic Sci. Int., 10 Jan 2012, 214 (1–3), 182-188. 1.4 MB. https://doi.org/10.1016/j.forsciint.2011.08.005

Oberlender, R; Nichols, DE. (+)-N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3,4-methylenedioxymethamphetamine-like behavioral activity. J. Pharmacol. Exp. Ther., 1 Dec 1990, 255 (3), 1098–1106. 1.9 MB.

Casale, JF; Hays, PA. Characterization of the “methylenedioxy-2-aminoindans”. Microgram J., 1 Jan 2011, 8 (2), 43–52. 1.3 MB.

Iversen, L; Gibbons, S; Treble, R; Setola, V; Huang, X; Roth, BL. Neurochemical profiles of some novel psychoactive substances. Eur. J. Pharmacol., 30 Jan 2013, 700 (1–3), 147–151. 490 kB. https://doi.org/10.1016/j.ejphar.2012.12.006

Corkery, JM; Elliott, S; Schifano, F; Corazza, O; Ghodse, AH. MDAI (5,6-methylenedioxy-2-aminoindane; 6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine; “sparkle”; “mindy”) toxicity: a brief overview and update. Hum. Psychopharmacol. Clin. Exp., 1 Jul 2013, 28 (4), 345–355. 157 kB. https://doi.org/10.1002/hup.2298

EMCDDA. New drugs in Europe, 2010, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 May 2011. 700 kB.

Jones, LE; Stewart, A; Peters, KL; McNaul, M; Speers, SJ; Fletcher, NC; Bell, SEJ. Infrared and Raman screening of seized novel psychoactive substances: a large scale study of >200 samples. Analyst, 25 Jan 2016, 141 (3), 902–909. 1.3 MB. https://doi.org/10.1039/c5an02326b

Burns, L; Roxburgh, A; Bruno, R; Van Buskirk, J. Monitoring drug markets in the Internet age and the evolution of drug monitoring systems in Australia. Drug Test. Anal., 1 Jul 2014, 6 (7-8), 840-845. 113 kB. https://doi.org/10.1002/dta.1613

Nichols, DE; Oberlender, R. Structure-activity relationships of MDMA-like substances. In Pharmacology and Toxicology of Amphetamine and Related Designer Drugs. NIDA Research Monograph 94; Asghar, K; De Souza, E, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1989; pp 1-29. 282 kB.

Simmler, LD; Liechti, ME. Pharmacology of MDMA- and amphetamine-like new psychoactive substances. In New Psychoactive Substances : Pharmacology, Clinical, Forensic and Analytical Toxicology; Maurer, HH; Brandt, SD, Eds., Springer, Berlin, Heidelberg, 1 Jan 2018; pp 143-164. 298 kB. https://doi.org/10.1007/164_2018_113

Chapman, SJ. Novel Psychoactive Spectra: NMR of (mostly) Novel Psychoactive Substances. BLOTTER, 25 Jun 2018, 3 (2). https://doi.org/10.16889/isomerdesign-6 #MDAI NMR

Nichols, DF; Oberlender, R. Structure-activity relationships of MDMA and related compounds: A new class of psychoactive agents? In Ecstasy: The Clinical, Pharmacological and Neurotoxicological Effects of the Drug MDMA; Peroutka, SJ, Ed., Springer US, 1 Jan 1990; pp 105–131. 733 kB. https://doi.org/10.1007/978-1-4613-1485-1_7 #16

Monte, AP; Marona-Lewicka, D; Cozzi, NV; Nichols, DE. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine. J. Med. Chem., 1 Nov 1993, 36 (23), 3700–3706. 1.0 MB. https://doi.org/10.1021/jm00075a027 MS,NMR

Luethi, D; Liechti, ME. Monoamine transporter and receptor interaction profiles in vitro predict reported human doses of novel psychoactive stimulants and psychedelics. Int. J. Neuropsychoph., 1 Oct 2018, 21 (10), 926–931. 254 kB. https://doi.org/10.1093/ijnp/pyy047 #S1 Aminoindanes MDAI

Halberstadt, AL; Brandt, SD; Walther, D; Baumann, MH. 2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α₂-adrenergic receptors. Psychopharmacology, 23 Mar 2019, n/a. 541 kB. https://doi.org/10.1007/s00213-019-05207-1 #MDAI

Kraemer, M; Boehmer, A; Madea, B; Maas, A. Death cases involving certain new psychoactive substances: A review of the literature. Forensic Sci. Int., 1 May 2019, 298 186–267. 6.7 MB. https://doi.org/10.1016/j.forsciint.2019.02.021 #MDAI

Oberlender, RA. Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 May 1989. 8.2 MB. #5,6-MDAI MS,NMR,IR,other

Åstrand, A; Guerrieri, D; Vikingsson, S; Kronstrand, R; Green, H. In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT_1A, and 5-HT2_A receptors—On-target receptor potency and efficacy, and off-target effects. Forensic Sci. Int., 1 Dec 2020, 317 110553. 1.7 MB. https://doi.org/10.1016/j.forsciint.2020.110553 #MDAI

Simmler, LD; Rickli, A; Schramm, Y; Hoener, MC; Liechti, ME. Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives. Biochem. Pharmacol., 15 Mar 2014, 88 (2), 237–244. 504 kB. https://doi.org/10.1016/j.bcp.2014.01.024 #MDAI

4,5-MDAI

MDCPA

MDHH-4 · TDIQ

10211

12188

APAA

4-Hydroxytryptophol

5-Hydroxytryptophol

7 Dec 2019 · · Isomer Design