5,6-Methylenedioxy-2-aminoindane
Encyclopedia
5,6-Methylenedioxy-2-aminoindane (MDAI) 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.
of MDAI is indirectly derived from that of the illicit drug MDA
, but the alpha-methyl group
of the alkylamino amphetamine
side chain has been bound back to the benzene
nucleus to form an indane
ring system, which changes its pharmacological properties substantially.
, a hallucinogen cue typified by drugs such as LSD
and DOM
, and an "entactogen-like" cue which is produced by drugs such as MDAI and MBDB
. These drugs cause drug-appropriate responses in animals trained to recognize the effects of MDMA, but do not produce responses in animals trained selectively to respond to stimulants or hallucinogens. Because these compounds selectively release serotonin in the brain but have little effect on dopamine or noradrenaline levels, they can produce empathogenic effects but without any stimulant action, instead being somewhat sedating.
values of 512nM, 5,920nM, and 1,426nM, 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.
which may be associated with MDMA and some related drugs. No test have been performed on cardiovascular toxicity.
. An analysis of two products on sale on the internet in June 2010 found that one contained mephedrone and that the other had an inorganic composition. Neither contained MDAI. MDAI is only non-neurotoxic in isolation but may become neurotoxic when mixed with other drugs.
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 vitro
In vitro
In vitro refers to studies in experimental biology that are conducted using components of an organism that have been isolated from their usual biological context in order to permit a more detailed or more convenient analysis than can be done with whole organisms. Colloquially, these experiments...
and produces entactogen effects in humans.
Chemistry
The chemical structureChemical structure
A chemical structure includes molecular geometry, electronic structure and crystal structure of molecules. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together. Molecular geometry can range from the very simple, such as...
of MDAI is indirectly derived from that of the illicit drug MDA
3,4-Methylenedioxyamphetamine
3,4-Methylenedioxyamphetamine , also known as tenamfetamine , is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes...
, but the alpha-methyl group
Methyl group
Methyl group is a functional group derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH3. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion...
of the alkylamino amphetamine
Amphetamine
Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...
side chain has been bound back to the benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
nucleus 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, which changes its pharmacological properties substantially.
Effects
The family of drugs typified by MDMA produce their effects through multiple mechanisms of action in the body, and consequently produce three distinct cues which animals can be trained to respond to: a stimulant cue typified by drugs such as methamphetamineMethamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...
, a hallucinogen cue typified by drugs such as LSD
LSD
Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...
and DOM
2,5-Dimethoxy-4-methylamphetamine
2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine...
, and an "entactogen-like" cue which is produced by drugs such as MDAI and MBDB
MBDB
Methylbenzodioxolylbutanamine is an entactogen of the phenethylamine chemical class. MBDB is a closely related chemical analogue of MDMA, with the only difference between the two molecules being an ethyl group instead of a methyl group attached to the alpha carbon.MBDB was first synthesized by...
. These drugs cause drug-appropriate responses in animals trained to recognize the effects of MDMA, but do not produce responses in animals trained selectively to respond to stimulants or hallucinogens. Because these compounds selectively release serotonin in the brain but have little effect on dopamine or noradrenaline levels, they can produce empathogenic effects but without any stimulant action, instead being somewhat sedating.
Pharmacology
MDAI has been shown to inhibit the reuptake of serotonin, dopamine, and norepinephrine with IC50IC50
The half maximal inhibitory concentration is a measure of the effectiveness of a compound in inhibiting biological or biochemical function. This quantitative measure indicates how much of a particular drug or other substance is needed to inhibit a given biological process by half...
values of 512nM, 5,920nM, and 1,426nM, respectively. This demonstrates that MDAI has selective affinity for the serotonin transporter
Serotonin transporter
The serotonin transporter is a monoamine transporter protein.This protein is an integral membrane protein that transports the neurotransmitter serotonin from synaptic spaces into presynaptic neurons. This transport of serotonin by the SERT protein terminates the action of serotonin and recycles it...
(SERT). In animals treated with reserpine
Reserpine
Reserpine is an indole alkaloid antipsychotic and antihypertensive drug that has been used for the control of high blood pressure and for the relief of psychotic symptoms, although because of the development of better drugs for these purposes and because of its numerous side-effects, it is rarely...
and MDAI, greater extracellular concentrations of monoamine neural transmitters
Monoamine neurotransmitter
thumb|right|350px| A phylogenetic tree showing how a number of monoamine receptors are related to each other.Monoamine neurotransmitters are neurotransmitters and neuromodulators that contain one amino group that is connected to an aromatic ring by a two-carbon chain...
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.
Use in scientific research
MDAI and other similar drugs have been widely used in scientific research, as they are able to replicate many of the effects of MDMA, but without causing the neurotoxicityNeurotoxicity
Neurotoxicity occurs when the exposure to natural or artificial toxic substances, which are called neurotoxins, alters the normal activity of the nervous system in such a way as to cause damage to nervous tissue. This can eventually disrupt or even kill neurons, key cells that transmit and process...
which may be associated with MDMA and some related drugs. No test have been performed on cardiovascular toxicity.
Use as a recreational drug
MDAI has been advertised as a designer drugDesigner drug
Designer drug is a term used to describe drugs that are created to get around existing drug laws, usually by preparing analogs or derivatives of existing drugs by modifying their chemical structure to varying degrees, or less commonly by finding drugs with entirely different chemical structures...
. An analysis of two products on sale on the internet in June 2010 found that one contained mephedrone and that the other had an inorganic composition. Neither contained MDAI. MDAI is only non-neurotoxic in isolation but may become neurotoxic when mixed with other drugs.
See also
- 2-Aminoindane2-Aminoindane2-Aminoindane is a psychoactive drug and research chemical with stimulant properties. It is a rigid analogue of amphetamine and partially substitutes for it in rat discrimination tests.-Chemical Derivatives:...
- 5-IAI5-Iodo-2-aminoindane5-Iodo-2-aminoindane is a drug which acts as a releasing agent of serotonin, norepinephrine, and dopamine. It was developed in the 1990s by a team led by David E. Nichols at Purdue University. 5-IAI fully substitutes for MDMA in rodents and is a putative entactogen in humans...
- AMMI1-Aminomethyl-5-methoxyindane1-Aminomethyl-5-methoxyindane , is a drug developed by a team led by David E. Nichols at Purdue University, which acts as a selective serotonin releasing agent and binds to the serotonin transporter with similar affinity to DFMDA....
- DFMDADifluoromethylenedioxyamphetamineDifluoromethylenedioxyamphetamine is a substituted derivative of methylenedioxyamphetamine , which was developed by Daniel Trachsel and coworkers, along with the corresponding fluorinated derivatives of MDMA, MDEA, BDB and MBDB, with the aim of finding a non-neurotoxic drug able to be used as a...
- MMAI5-Methoxy-6-methyl-2-aminoindane5-Methoxy-6-methyl-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 and produces entactogen effects in humans...
- MDMAI5,6-Methylenedioxy-N-methyl-2-aminoindane5,6-Methylenedioxy-N-methyl-2-aminoindane , is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University...
- MDAT