2-AI, or 2-Aminoindane, is a structural analogue of amphetamine. It features the R3 terminal carbon of the propane chain of amphetamine bound to the benzene ring. This creates an indane group, a bicyclic moeity containing a benzene ring fused to a pentane ring. 2-AI contains an amino group NH2 bound to R2 of the indane ring thus giving it the name 2-aminoindane. 2-AI is structurally analogous to NM-2-AI, lacking the N-substituted methyl group.The prototype aminoindane, 2-aminoindane (2-AI), is a cyclic analogue of amphetamine (see Figure 1). The 2-AI backbone structure can be modified to produce diverse chemical substances by substitution on the aromatic ring with a variety of functional groups, or the addition of a methylenedioxy bridge or N-alkylation; generating the following substances, respectively: 5-iodo-2-aminoindane (5-IAI, Figure 2c), 5,6-methylenedioxy-2-aminoindane (MDAI, Figure 2b) and N-methyl-2-aminoindane (NM-2AI, Figure 2d). Analogues of aminoindanes can be prepared using indanone, indene or after intramolecular cyclization of the acyl chloride derivative of 3-phenyl-2-propanoic acid.
Street names of MDAI include ‘MDAI gold’, while 2-AI has been found in party pills known as ‘Pink Champagnes’ . Aminoindanes are commonly found in powder form and crystals and are usually ingested, but snorting is also possible.
Aminoindanes act predominantly as central nervous system stimulants. Stimulants mediate the actions of dopamine, norepinephrine and/or serotonin, mimicking the effects of traditional drugs such as cocaine, amphetamine, methamphetamine, and ecstasy.
Reported adverse effects
Research conducted in animals and in in vitro cell cultures indicates that aminoindanes are relatively benign at recreational doses; however, the effects on humans have not yet been reported . Animal studies have shown that these substances did not present any long-term neurotoxicity at the levels administered, [2,3,9] but slight neurotoxicity in rodents was shown after administration of very high doses of 5-IAI .