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When given, the molecule known as 5,6-methylenedioxy-2-aminoindane, which belongs to the chemical class known as aminoindane, is capable of producing entactogenic effects. Notably, this molecule is principally responsible for producing the non-stimulating effects of archetypal entactogens like MDMA. These effects include drowsiness, relaxing of muscular tissue, and augmentation of tactile sensitivity.
However, very little study has been done on humans to investigate the effects of MDAI, despite the fact that it is known to induce effects that make individuals feel closer and more loving to others (empathogenic).
Chemically speaking, MDAI is produced from the substance known as MDA, which has been available since the 1940s and reached its peak of popularity in the 1960s (See MDA section). There hasn’t been a lot of study done on the possible negative effects and addictive qualities of the substance known as 5,6-methylenedioxy-2-aminoindane.
It has been shown that MDAI is capable of inhibiting the reuptake of serotonin and has been found to have a specific affinity for the serotonin receptor. Studies have shown that rats whose brains were treated with 5,6-methylenedioxy-2-aminoindane had increased extracellular quantities of monoamine neuro transmitters, most substantially serotonin.
Pharmaceutical Analysis of MDAI
To put this into perspective, the potency of MDAI in terms of releasing serotonin is comparable to that of MDA, but it is substantially less powerful than MDMA.
This is accomplished by inhibiting the reuptake and reabsorption of the neurotransmitters after they have performed their function of transmitting a neural impulse. This essentially gives the neurotransmitters permission to accumulate, enables them to be reused, and produces effects that are entactogenic.
It has been shown that 5,6-methylenedioxy-2-aminoindane powerfully stimulates the release of the neurotransmitter serotonin in research models; hence, it is able to be referred to as a “selective serotonin releasing agent” (SSRA). Serotonin, also known as 5-hydroxytryptamine, is primarily located in the intestines as well as the central nervous system. It has a role in the regulation of a variety of functions, including bowel movement, sleep, mood, hunger, learning, and memory.
The degree to which MDAI promotes the release of serotonin is equivalent to that seen with MDA, although it is much less than that observed with 3, 4-methylenedioxy-N-methylamphetamine (MDMA).
MDAI has also been found to inhibit the reuptake, or movement back into cells, of serotonin, as well as (to a lesser degree) the reuptake of the neurotransmitters dopamine and norepinephrine. Dopamine is involved in the regulation of behavior associated with seeking rewards, and norepinephrine is involved in the regulation of blood pressure (or noradrenaline –a primary stress hormone).
The Chemistry Behind MDAI
The synthetic chemical known as 5,6-methylenedioxy-2-aminoindane, or MDAI for short, belongs to the family of aminoindane compounds and has structural similarities with amphetamines. It is distinguished by the presence of the R3 terminal carbon of the amphetamine’s propane chain bonded to the benzene ring. This results in the formation of an indane group, which is a bicyclic molecule that has a benzene ring that has been fused to a pentane ring. 5,6-Methylenedioxy-2-aminoindane has an amino group NH2 attached to R2 of the indane ring. A methylenedioxy group is also formed by MDAI thanks to the presence of two oxygen substitutions at positions R5 and R6, which are connected by a methylene bridge. The only structural difference between MDAI and 2-AI is the presence of a methylenedioxy ring in MDAI.
5,6-Methylenedioxy-2-aminoindane to give it its full name in the chemist’s notation
The IUPAC name for this compound is 6,7-dihydro-5H-cyclopenta[f][1,3].
CAS Number: 132741-81-2
ChemSpider Number: 111694
Molecular Formula: C10H11NO2
The number of grams per mole is 177.1998.