5,6-Methylenedioxy-N-methyl-2-aminoindane

5,6-Methylenedioxy-N-methyl-2-aminoindane (MDMAI), is a drug

Drug

A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...

developed in the 1990s by a team led by David E. Nichols

David E. Nichols

David E. Nichols is an American pharmacologist and medicinal chemist.Presently the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichols has worked in the field of psychoactive drugs since 1969...

at Purdue University

Purdue University

Purdue University, located in West Lafayette, Indiana, U.S., is the flagship university of the six-campus Purdue University system. Purdue was founded on May 6, 1869, as a land-grant university when the Indiana General Assembly, taking advantage of the Morrill Act, accepted a donation of land and...

. It acts as a non-neurotoxic and highly selective

Binding selectivity

Binding selectivity refers to the differing affinities with which different ligands bind to a substrate forming a complex. A selectivity coefficient is the equilibrium constant for the reaction of displacement by one ligand of another ligand in a complex with the substrate...

serotonin releasing agent

Selective serotonin releasing agent

A selective serotonin releasing agent is a type of drug which selectively induces the release of serotonin from the pre-synaptic neuron into the synapse...

(SSRA) in animals and a putative entactogen

Empathogen-entactogen

The terms empathogen and entactogen are used to describe a class of psychoactive drugs that produce distinctive emotional and social effects similar to those of MDMA. Putative members of this class include 2C-B, 2C-I, MDMA, MDA, MDEA, MBDB, 2C-T-7, and 2C-T-2, among others...

in humans.

Chemistry

MDMAI can be thought of as a cyclised analogue

Analog (chemistry)

In chemistry, a structural analog , also known as chemical analog or simply analog, is a compound having a structure similar to that of another one, but differing from it in respect of a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced...

of MDMA where the alpha-methyl carbon of the alkylamino side chain has been joined back round to the 6-position of the aromatic ring to form an indane

Indane

Indane or indan is a hydrocarbon petrochemical compound.-Derivatives:Derivatives include compounds such as 1-methyl-indane and 2-methyl-indane , 4-methyl-indane and 5-methyl-indane , various dimethyl-indanes, and various pharmaceutical derivatives...

ring system. This changes the core structure of the molecule from phenethylamine

Phenethylamine

Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...

to aminoindane, and causes the pharmacological properties of the two compounds to be substantially different.

Chemistry

See also