''N''-Methyltryptamine (NMT), also known as monomethyltryptamine, is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

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 ...

family and a

naturally occurring A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical ...

compound found in the human body and certain plants. It is biosynthesized in humans from

by certain ''N''-methyltransferase

enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...

s, such as indolethylamine ''N''-methyltransferase. It is a known component in human urine. NMT is an

alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...

derived from L-tryptophan that has been found in the bark, shoots and

leaves A leaf (: leaves) is a principal appendage of the stem of a vascular plant, usually borne laterally above ground and specialized for photosynthesis. Leaves are collectively called foliage, as in "autumn foliage", while the leaves, stem, ...

of several plant

genera Genus (; : genera ) is a taxonomic rank above species and below family as used in the biological classification of living and fossil organisms as well as viruses. In binomial nomenclature, the genus name forms the first part of the binomial s ...

, including '' Virola'', ''

Acacia ''Acacia'', commonly known as wattles or acacias, is a genus of about of shrubs and trees in the subfamily Mimosoideae of the pea family Fabaceae. Initially, it comprised a group of plant species native to Africa, South America, and Austral ...

'', '' Mimosa'', and '' Desmanthus''—often together with the related compounds ''N'',''N''-dimethyltryptamine (DMT) and 5-methoxy-''N'',''N''-dimethyltryptamine (5-MeO-DMT). NMT acts as a serotonin receptor agonist and serotonin releasing agent and is said to produce

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 ...

ic effects in humans.

Effects

Orally administered NMT appears to produce no

psychoactive A psychoactive drug, psychopharmaceutical, mind-altering drug, consciousness-altering drug, psychoactive substance, or psychotropic substance is a chemical substance that alters psychological functioning by modulating central nervous system acti ...

effects, likely as a result of extensive

first-pass metabolism The first pass effect (also known as first-pass metabolism or presystemic metabolism) is a phenomenon of drug metabolism at a specific location in the body which leads to a reduction in the concentration of the active drug before it reaches the ...

. Per Roger W. Brimblecombe and colleagues, NMT is inactive in humans, with few details provided. On the other hand, according to Alexander Shulgin and others, NMT is active via non-oral routes. It has been said to produce psychedelic effects at doses of 50 to 120mg by

smoking Smoking is a practice in which a substance is combusted, and the resulting smoke is typically inhaled to be tasted and absorbed into the bloodstream of a person. Most commonly, the substance used is the dried leaves of the tobacco plant, whi ...

vaporization Vaporization (or vapo(u)risation) of an element or compound is a phase transition from the liquid phase to vapor. There are two types of vaporization: evaporation and boiling. Evaporation is a surface phenomenon, whereas boiling is a bulk phenome ...

, with a duration of seconds to minutes. Based on preliminary reports, NMT is reported to produce

visual The visual system is the physiological basis of visual perception (the ability to detect and process light). The system detects, transduces and interprets information concerning light within the visible range to construct an image and buil ...

s, but its effects are described as primarily spatial in nature, among other effects. NMT has also been reported to be orally active in

combination In mathematics, a combination is a selection of items from a set that has distinct members, such that the order of selection does not matter (unlike permutations). For example, given three fruits, say an apple, an orange and a pear, there are ...

with a

monoamine oxidase inhibitor Monoamine oxidase inhibitors (MAOIs) are a drug class, 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 antidepressa ...

(MAOI).

Pharmacology

NMT is known to act as a potent

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT_2A receptor full agonist ( = 50.7nM; = 96%). It has been reported to be inactive in activating the β-arrestin pathway of the receptor and hence appears to be a biased agonist of the serotonin 5-HT_2A receptor. In contrast to the serotonin 5-HT_2A receptor, the drug is not an agonist of the serotonin 5-HT_1A receptor. In addition to its serotonin 5-HT_2A receptor agonism, NMT is a potent serotonin releasing agent ( = 22.4nM). It also releases

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...

and

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic compound, organic chemical in the catecholamine family that functions in the brain and human body, body as a hormone, neurotransmitter and neuromodulator. The ...

much more weakly ( = 321nM and 733nM, respectively; 14- and 33-fold less than for serotonin, respectively).

Society and culture

Legal status

In the United States NMT is considered a schedule 1 controlled substance as an positional isomer of Alpha-methyltryptamine (AMT).

References

External links