MDAI

MDAI

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	Illegal in China
Identifiers
IUPAC name 6,7-Dihydro-5H-cyclopenta[f] [1,3]benzodioxol-6-amine
CAS Number	132741-81-2
PubChem CID	125558
ChemSpider	111694 Y
UNII	0DMJ6G3XBF
Chemical and physical data
Formula	C10H11NO2
Molar mass	177.1998 g/mol
3D model (Jmol)	Interactive image
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 (5,6-methylenedioxy-2-aminoindane) is a drug 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 vitro and produces entactogen effects in humans.

The chemical structure of MDAI is indirectly derived from that of the illicit drug MDA, but the alpha-methyl group of the alkyl amino amphetamine side chain has been bound back to the benzene nucleus to form an indane ring system, which changes its pharmacological properties substantially.

MDAI can be produced from 3-(3,4-methylenedioxyphenyl)propionic acid which is converted to the acid chloride and then heated to produce 5,6-Methylenedioxy-1-indanone. Treatment of the indanone with amyl nitrite in methanol with HCl afforded the hydroxyimino ketone. This is reduced to the 2-aminoindan following a modification of Nichols' earlier method from a paper discussing DOM analogues, using a Pd/C catalyst in glacial acetic acid with catalytic H₂SO₄.

MDAI has been shown to inhibit the reuptake of serotonin, dopamine, and norepinephrine with IC₅₀ values of 512 nM, 5,920 nM, and 1,426 nM, respectively. This demonstrates that MDAI has selective affinity for the serotonin transporter (SERT). In animals treated with reserpine and MDAI, greater extracellular concentrations of monoamine neural transmitters resulted, most significantly serotonin. This result indicates that MDAI is a potent releaser of serotonin, while effectively inhibiting the reuptake of serotonin. For comparison, MDAI is similar in potency with releasing serotonin to MDA but significantly less potent than MDMA.