3-Methyl-4,5-methylenedioxyamphetamine

5-Methyl-3,4-methylenedioxyamphetamine (5-Methyl-MDA) is an entactogen and psychedelic

Psychedelic drug

A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...

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...

of the amphetamine

Substituted amphetamine

Substituted amphetamines are a chemical class of stimulants, entactogens, hallucinogens, and other drugs. They feature a phenethylamine core with a methyl group attached to the alpha carbon resulting in amphetamine, along with additional substitutions...

class. It is a ring

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...

-methylated derivative of MDA

3,4-Methylenedioxyamphetamine

3,4-Methylenedioxyamphetamine , also known as tenamfetamine , is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes...

and a structural isomer of MDMA. Drug discrimination

Classical conditioning

Classical conditioning is a form of conditioning that was first demonstrated by Ivan Pavlov...

studies showed that 5-methyl-MDA substitutes for MDA, MMAI

5-Methoxy-6-methyl-2-aminoindane

5-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...

, and LSD, but not 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,...

, suggesting that it produces a mix of entactogen and hallucinogenic effects without any stimulant

Stimulant

Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...

effects.

5-Methyl-MDA acts as a selective 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) with IC₅₀

IC50

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 107nM, 11,600nM, and 1,494nM for serotonin

Serotonin

Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...

, dopamine

Dopamine

Dopamine is a catecholamine neurotransmitter present in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this substituted phenethylamine functions as a neurotransmitter, activating the five known types of dopamine receptors—D1, D2, D3, D4, and D5—and their...

, and norepinephrine

Norepinephrine

Norepinephrine is the US name for noradrenaline , a catecholamine with multiple roles including as a hormone and a neurotransmitter...

efflux. It is over 5x more potent than MDA, with a suitable active dose possibly being around 15-25 mg. 2-Methyl-MDA

2-Methyl-MDA

2-Methyl-3,4-methylenedioxyamphetamine is an entactogen and psychedelic drug of the amphetamine class. It acts as a selective serotonin releasing agent , with IC50 values of 93nM, 12,000nM, and 1,937nM for serotonin, dopamine, and norepinephrine efflux. 2-Methyl-MDA is more potent than MDA,...

is also much more potent than MDA, but is not quite as potent as 5-methyl-MDA. Both 6-methyl-MDA

6-Methyl-MDA

6-Methyl-3,4-methylenedioxyamphetamine is an entactogen and psychedelic drug of the amphetamine class. It was first synthesized in the late 1990s by a team including David E...

and 6-methyl-MDMA

Madam-6

Madam-6, or 2,N-dimethyl-4,5-methylenedioxyamphetamine, is a lesser-known hallucinogenic psychedelic drug. Madam-6 was first synthesized by Alexander Shulgin. In his book PiHKAL , the minimum dosage is listed as 280 mg, and the duration unknown. Madam-6 produces few to no effects...

(also known as Madam-6) are inactive, likely due to steric hindrance.

Recent research has used data on 2-methyl-MDA and 5-methyl-MDA to help guide computer modeling of 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...

complex.

The synthesis

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...

of 5-methyl-MDA can be found online.

See also