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''N''-Methyltryptamine (NMT) is a member of the
substituted tryptamine Substituted tryptamines, or serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino group, amino (NH2) group ...
chemical class Chemical classification systems attempt to classify elements or compounds according to certain chemical functional or structural properties. Whereas the structural properties are largely intrinsic, functional properties and the derived classificat ...
and a
natural product 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 syn ...
which is
biosynthesized Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. ...
in the human body from
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 f ...
by certain
N-methyltransferase N-methyltransferase may refer to: * (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline N-methyltransferase * 3-hydroxy-16-methoxy-2,3-dihydrotabersonine N-methyltransferase * Amine N-methyltransferase * Anthranilate N-methyltransferase * (cytochrome c)-a ...
enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. A ...
s, such as indolethylamine ''N''-methyltransferase. It is a common component in human urine. NMT is an
alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...
derived from L-tryptophan that has been found in the bark,
shoot In botany, a plant shoot consists of any plant stem together with its appendages, leaves and lateral buds, flowering stems, and flower buds. The new growth from seed germination that grows upward is a shoot where leaves will develop. In the spri ...
s and
leaves A leaf (plural, : leaves) is any of the principal appendages of a vascular plant plant stem, stem, usually borne laterally aboveground and specialized for photosynthesis. Leaves are collectively called foliage, as in "autumn foliage", wh ...
of several plant
genera Genus ( plural genera ) is a taxonomic rank used in the biological classification of living and fossil organisms as well as viruses. In the hierarchy of biological classification, genus comes above species and below family. In binomial nomenclat ...
, including ''
Virola ''Virola'' is a genus of medium-sized trees native to the South American rainforest and closely related to other Myristicaceae, such as nutmeg. Species are known commonly as ''epená'', ''patricá'', or ''cumala''. They have glossy, dark green le ...
'', ''
Acacia ''Acacia'', commonly known as the wattles or acacias, is a large genus of shrubs and trees in the subfamily Mimosoideae of the pea family Fabaceae. Initially, it comprised a group of plant species native to Africa and Australasia. The genus na ...
'', ''
Mimosa ''Mimosa'' is a genus of about 590 species of herbs and shrubs, in the mimosoid clade of the legume family Fabaceae. The generic name is derived from the Greek word (''mimos''), an "actor" or "mime", and the feminine suffix -''osa'', "resembl ...
'', and ''
Desmanthus ''Desmanthus'' is a genus of flowering plants in the mimosoid clade of the subfamily Caesalpinioideae of the pea family, Fabaceae. The name is derived from the Greek words δεσμός (''desmos''), meaning "bundle", and ἄνθος (''anthos' ...
''—often together with the related
compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fortified with defensive struct ...
s ''N'',''N''-dimethyltryptamine (DMT) and 5-methoxy-''N'',''N''-dimethyltryptamine (5-MeO-DMT). Orally administered NMT appears to produce no
psychoactive A psychoactive drug, psychopharmaceutical, psychoactive agent or psychotropic drug is a chemical substance, that changes functions of the nervous system, and results in alterations in perception, mood, consciousness, cognition or behavior. Th ...
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 whereby the concentration of a drug, specifically when administered orally, is greatly reduced before it reaches the systemi ...
.Foye's principles of medicinal chemistry By William O. Foye, Thomas L. Lemke, David A. Williams However, it may become
active Active may refer to: Music * ''Active'' (album), a 1992 album by Casiopea * Active Records, a record label Ships * ''Active'' (ship), several commercial ships by that name * HMS ''Active'', the name of various ships of the British Royal ...
upon
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 th ...
with a MAOA inhibitor (MAOI). By vaporization NMT shows activity at 50–100 mg, with a duration of 45–70 minutes; duration of visual effects 15–30 seconds. Effects are primarily non-visual.Nen - lecture presented EGA conference, Victoria, Australia 4/12/2011; and Breaking Conventions, London 12/7/2013.


See also

* ''N''-Ethyltryptamine (NET) * ''N'',''N'',-Dimethyltryptamine (DMT) * ''
Acacia confusa ''Acacia confusa'' is a perennial tree native to South-East Asia. Some common names for it are acacia petit feuille, Ayangile, small Philippine acacia, Formosa acacia (Taiwan acacia), Philippine Wattle, and Formosan koa. It grows to a height of 1 ...
'' (a natural source of NMT, with other tryptamines, 1.63%. Buchanan et al. 2007) * ''
Acacia obtusifolia ''Acacia obtusifolia'', commonly known as stiff-leaf wattle or blunt-leaf wattle, is a perennial tree in subfamily Mimosoideae of family Fabaceae. Description ''Acacia obtusifolia'' is an upright or spreading perennial tree which grows from 1. ...
'' (NMT up to 2/3 alkaloid content) * '' Acacia simplicifolia (synon. A. simplex) (1.44% NMT in bark, 0.29% twigs, Pouet ''et al.'' 1976) * ''
Desmanthus illinoensis ''Desmanthus illinoensis'', commonly known as Illinois bundleflower, prairie-mimosa or prickleweed, is a common plant in many areas of the south central and Midwestern US. Habitat It can often be found growing on the sides of roads, needing fu ...
'' (NMT major component seasonally)


References


External links


NMT Entry in ''TIHKAL''

NMT Entry in TiHKAL • info
{{DEFAULTSORT:Methyltryptamine, N- Tryptamine alkaloids Psychedelic tryptamines Serotonin receptor agonists