3-Methoxy-4-methylamphetamine
Encyclopedia
3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic
drug
of the phenethylamine
and amphetamine
classes. It was first synthesized
in 1970 and was encountered as a street drug in Italy
in the same decade. MMA was largely forgotten until being reassayed by David E. Nichols
as a non-neurotoxic MDMA analogue in 1991, and has subsequently been sold as a designer drug
on the internet since the late 2000s.
In animal studies, MMA fully substitutes for MDMA and MBDB
, partially substitutes for LSD
, and does not substitute for amphetamine
. Additionally, it has been shown to potent
ly inhibit
the reuptake
of serotonin
and does not produce serotonergic
neurotoxicity
in rodents. These data appear to confer a profile of MMA as a selective serotonin releasing agent
(SSRA) and 5-HT2A receptor
agonist
.
According to anecdotal reports, MMA is active in humans at doses of 20-60 mg and possesses a duration of approximately 12-16 hours. It is said to produce empathy
and mild 2C
-like psychedelic
effects, and although it is mood-lifting, it is not euphoric
like MDMA and is more antidepressant
-like in comparison. At higher doses, such as 140 mg, the effects are much more psychedelic (comparable to DOM
) but can be dysphoric and very long-lived.
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 phenethylamine
Substituted phenethylamine
The substituted phenethylamines are chemical compounds with the 2-phenethylamine chemical structure modified at the phenyl ring, sidechain, and/or amino group. Some of them are psychoactive drugs, including stimulants, psychedelics, opioids, and entactogens, which exert their effects primarily...
and 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...
classes. It was first synthesized
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...
in 1970 and was encountered as a street drug in Italy
Italy
Italy , officially the Italian Republic languages]] under the European Charter for Regional or Minority Languages. In each of these, Italy's official name is as follows:;;;;;;;;), is a unitary parliamentary republic in South-Central Europe. To the north it borders France, Switzerland, Austria and...
in the same decade. MMA was largely forgotten until being reassayed 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...
as a non-neurotoxic MDMA analogue in 1991, and has subsequently been sold as a designer drug
Designer 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...
on the internet since the late 2000s.
In animal studies, MMA fully substitutes for MDMA 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...
, partially substitutes for 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 does not substitute for 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,...
. Additionally, it has been shown to potent
Potency (pharmacology)
In the field of pharmacology, potency is a measure of drug activity expressed in terms of the amount required to produce an effect of given intensity. A highly potent drug evokes a larger response at low concentrations, while a drug of lower potency evokes a small response at low concentrations...
ly inhibit
Reuptake inhibitor
A reuptake inhibitor , also known as a transporter blocker, is a drug that inhibits the plasmalemmal transporter-mediated reuptake of a neurotransmitter from the synapse into the pre-synaptic neuron, leading to an increase in the extracellular concentrations of the neurotransmitter and therefore an...
the reuptake
Reuptake
Reuptake, or re-uptake, is the reabsorption of a neurotransmitter by a neurotransmitter transporter of a pre-synaptic neuron after it has performed its function of transmitting a neural impulse....
of 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...
and does not produce serotonergic
Serotonergic
Serotonergic or serotoninergic means "related to the neurotransmitter serotonin". A synapse is serotonergic if it uses serotonin as its neurotransmitter...
neurotoxicity
Neurotoxicity
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...
in rodents. These data appear to confer a profile of MMA 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) and 5-HT2A receptor
5-HT2A receptor
The mammalian 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor . This is the main excitatory receptor subtype among the GPCRs for serotonin , although 5-HT2A may also have an inhibitory effect on certain areas such...
agonist
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
.
According to anecdotal reports, MMA is active in humans at doses of 20-60 mg and possesses a duration of approximately 12-16 hours. It is said to produce empathy
Empathy
Empathy is the capacity to recognize and, to some extent, share feelings that are being experienced by another sapient or semi-sapient being. Someone may need to have a certain amount of empathy before they are able to feel compassion. The English word was coined in 1909 by E.B...
and mild 2C
2C (psychedelics)
2C is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of the benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and longer acting...
-like psychedelic
Psychedelic
The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...
effects, and although it is mood-lifting, it is not euphoric
Euphoriant
A euphoriant is a type of psychoactive drug which tends to induce feelings of euphoria, the effects of which may include relaxation, anxiolysis, stress relief, mood lift, pleasure, and a rush although these effects are not necessary for a drug to be a euphoriant. Many euphoriants are notorious for...
like MDMA and is more antidepressant
Antidepressant
An antidepressant is a psychiatric medication used to alleviate mood disorders, such as major depression and dysthymia and anxiety disorders such as social anxiety disorder. According to Gelder, Mayou &*Geddes people with a depressive illness will experience a therapeutic effect to their mood;...
-like in comparison. At higher doses, such as 140 mg, the effects are much more psychedelic (comparable to DOM
2,5-Dimethoxy-4-methylamphetamine
2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine...
) but can be dysphoric and very long-lived.
See also
- 3-Methoxyamphetamine3-Methoxyamphetaminemeta-Methoxyamphetamine , also known as 3-methoxyamphetamine , is a stimulant drug from the amphetamine family...
(3-MeOA) - 3-Methoxymethamphetamine3-Methoxymethamphetamine3-Methoxymethamphetamine , is an amphetamine-derived stimulant drug, which is most closely related to 3-methoxyamphetamine and PMMA and shares similar monoamine releasing effects, although its effects have not been studied so extensively as other related drugs.- See also :* PMA* Fenfluramine*...
(MMMA) - 4-Methylamphetamine4-Methylamphetamine4-Methylamphetamine is a stimulant and anorectic drug of the phenethylamine and amphetamine chemical classes....
(4-MA) - 4-Methylmethamphetamine4-Methylmethamphetamine4-Methylmethamphetamine is a putative stimulant and entactogen drug of the amphetamine class. It is the β-deketo analogue of mephedrone.- See also :* 4-Methylamphetamine * 4-Methylmethcathinone * 3-Methoxymethamphetamine...
(4-MMA) - 4-Methylmethcathinone4-MethylmethcathinoneMephedrone, also known as 4-methylmethcathinone , or 4-methylephedrone, is a synthetic stimulant and entactogen drug of the amphetamine and cathinone classes. Slang names include meph, drone, and MCAT. It is reportedly manufactured in China and is chemically similar to the cathinone compounds found...
(4-MMC)