4-Methyl-α-methyltryptamine
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4-Methyl-α-methyltryptamine (4-Me-αMT or 4-Me-AMT), also known as 4,α-dimethyltryptamine (4,α-DMT) and by its developmental code name MP-809, is an
experimental An experiment is a procedure carried out to support or refute a hypothesis, or determine the efficacy or likelihood of something previously untried. Experiments provide insight into cause-and-effect by demonstrating what outcome occurs whe ...
antidepressant Antidepressants are a class of medications used to treat major depressive disorder, anxiety disorders, chronic pain, and addiction. Common side effects of antidepressants include Xerostomia, dry mouth, weight gain, dizziness, headaches, akathi ...
of the
tryptamine Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the firs ...
and
α-alkyltryptamine Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all trypt ...
families. It is closely structurally related to
serotonergic psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...
s and
entactogen Entactogens, also known as empathogens or connectogens, are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, connectedness, emotional openness—that is, empathy—as particularly observe ...
s like α-methyltryptamine (αMT) and
α-ethyltryptamine α-Ethyltryptamine (αET, AET), also known as etryptamine, is an entactogen and stimulant drug of the tryptamine family. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s before bei ...
(αET). 4-Me-αMT was investigated as an antidepressant by
Sandoz Sandoz Group AG is a Swiss company that focuses on generic pharmaceuticals and biosimilars. Prior to October 2023, it was part of a division of Novartis that was established in 2003, when Novartis united all of its generics businesses under the ...
in
Canada Canada is a country in North America. Its Provinces and territories of Canada, ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, making it the world's List of coun ...
in the early 1960s, although it was never marketed.


Dosage and effects

It is active at a dosage of 20 to 60mg orally in humans, though described as being an antidepressant rather than a
hallucinogen Hallucinogens, also known as psychedelics, entheogens, or historically as psychotomimetics, are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mo ...
. It was found to be effective as an antidepressant in preliminary
clinical studies Clinical trials are prospective biomedical or behavioral research studies on human participants designed to answer specific questions about biomedical or behavioral interventions, including new treatments (such as novel vaccines, drugs, dietar ...
.
Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...
has said that 4-Me-αMT produced some feelings of unreality at a dose of 20mg, as well as skin flushing, muscle tightness, and
mydriasis Mydriasis is the Pupillary dilation, dilation of the pupil, usually having a non-physiological cause, or sometimes a physiological pupillary response. Non-physiological causes of mydriasis include disease, Physical trauma, trauma, or the use of c ...
. However, he has said that it could not be called a hallucinogen at assessed doses and has listed the hallucinogenic dosage as being greater than 60mg.


Pharmacology

4-Me-αMT partially reverses
reserpine Reserpine is a drug that is used for the treatment of hypertension, high blood pressure, usually in combination with a thiazide diuretic or vasodilator. Large clinical trials have shown that combined treatment with reserpine plus a thiazide diur ...
-induced behavioral depression in rodents (by up to 60%), but does not produce
hyperlocomotion Locomotor activity is a measure of animal behavior which is employed in scientific research. Hyperlocomotion, also known as locomotor hyperactivity, hyperactivity, or increased locomotor activity, is an effect of certain drugs in animals in whi ...
. This was the case at a dose of 50mg/kg, whereas αMT produced clear hyperlocomotion and near-fully reversed reserpine-induced hypoactivity (by 95%) at a dose of 15mg/kg. Hence, 4-Me-αMT shows reduced antidepressant- and
psychostimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition ...
-like
potency Potency may refer to: * Potency (pharmacology), a measure of the activity of a drug in a biological system * Virility * Cell potency, a measure of the differentiation potential of stem cells * In homeopathic dilutions, potency is a measure of ho ...
compared to αMT. It is also less active than αET. The drug is said to have very weak
monoamine oxidase inhibition Monoamine oxidase inhibitors (MAOIs) are a class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressants, especia ...
.


History

4-Me-αMT was first described in the
scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...
by 1962.


See also

* 4-Methyl-αET * 4-HO-αMT *
RS134-49 RS134-49 is a tetrahydropyridine derivative related to psychedelic tryptamines which acts as a 5-HT2A receptor agonist, with a 5-HT2A Ki of 11.5nM and an EC50 of 22nM. It is a biased agonist selective for activation of the Gq coupled signalling ...


References


External links


4-Methyl-AMT - Isomer Design
{{DEFAULTSORT:Methyl-α-methyltryptamine, 4- Abandoned drugs Alpha-Alkyltryptamines Experimental antidepressants Methyl compounds Psychedelic tryptamines