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  • 2-(1H-Indol-3-yl)-N-methylethan-1-amine
CAS Number
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Chemical and physical data
Formula C11H14N2
Molar mass 174.247 g·mol−1
3D model (JSmol)
Melting point 87 to 89 °C (189 to 192 °F)
  • CNCCc1c[nH]c2ccccc12
  • InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3 Yes check.svgY
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N-Methyltryptamine (NMT) is a member of the substituted tryptamine chemical class and a natural product which is biosynthesized in the human body from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase. [1] [2] It is a common component in human urine. [3] NMT is an alkaloid derived from L-tryptophan that has been found in the bark, shoots and leaves of several plant genera, including Virola , Acacia , Mimosa , and Desmanthus —often together with the related compounds N,N-dimethyltryptamine (DMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).[ citation needed ]


Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism. [4] However, it may become active upon combination with a MAOA inhibitor (MAOI). [4] 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. [5] [6]


In the United States N-Methyltryptamine is considered a schedule 1 controlled substance as an positional isomer of Alpha-methyltryptamine (AMT) [7]

See also

Related Research Articles

<span class="mw-page-title-main">Ayahuasca</span> South American psychoactive brew

Ayahuasca is a South American psychoactive and entheogenic brewed drink traditionally used both socially and as a ceremonial or shamanic spiritual medicine among the indigenous peoples of the Amazon basin, and more recently in North America and Europe. The tea causes altered states of consciousness often known as "psychedelic experiences" which include visual hallucinations and altered perceptions of reality.

<i>N</i>,<i>N</i>-Dimethyltryptamine Chemical compound

N,N-Dimethyltryptamine is a substituted tryptamine that occurs in many plants and animals, including humans, and which is both a derivative and a structural analog of tryptamine. It is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.

<span class="mw-page-title-main">5-MeO-DMT</span> Chemical compound

5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine) or O-methyl-bufotenin is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the Colorado River toad. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include Five-methoxy, The power, and Toad venom.

A biogenic amine is a biogenic substance with one or more amine groups. They are basic nitrogenous compounds formed mainly by decarboxylation of amino acids or by amination and transamination of aldehydes and ketones. Biogenic amines are organic bases with low molecular weight and are synthesized by microbial, vegetable and animal metabolisms. In food and beverages they are formed by the enzymes of raw material or are generated by microbial decarboxylation of amino acids.

<span class="mw-page-title-main">5-MeO-DET</span> Chemical compound

5-MeO-DET or 5-methoxy-N,N-diethyltryptamine is a hallucinogenic tryptamine.

<i>Acacia obtusifolia</i> Species of legume

Acacia obtusifolia, commonly known as stiff-leaf wattle or blunt-leaf wattle, is a perennial tree in subfamily Mimosoideae of family Fabaceae.

<i>Vachellia rigidula</i> Species of plant

Vachellia rigidula, commonly known as blackbrush acacia or chaparro prieto, and also known as Acacia rigidula, is a species of shrub or small tree in the legume family, Fabaceae. Its native range stretches from Texas in the United States south to central Mexico. This perennial is not listed as being threatened. It reaches a height of 5–15 feet (1.5–4.6 m). Blackbrush acacia grows on limestone hillsides and canyons.

<span class="mw-page-title-main">5-MeS-DMT</span> Chemical compound

5-MeS-DMT (5-methylthio-N,N-dimethyltryptamine) is a lesser-known psychedelic drug. It is the 5-methylthio analog of dimethyltryptamine (DMT). 5-MeS-DMT was first synthesized by Alexander Shulgin. In his book TiHKAL, the minimum dosage is listed as 15-30 mg. The duration listed as very short, just like DMT. 5-MeS-DMT produces similar effects to DMT, but weaker. Shulgin describes his feelings while on a low dose of this drug as "pointlessly stoned", although at a higher dose of 20 mg he says it is "quite intense" and suggests that a higher dose still might have full activity.

<span class="mw-page-title-main">5-MeO-NMT</span> Chemical compound

5-MeO-NMT (5-methoxy-N-methyltryptamine) is an organic chemical compound, being the 5-methoxy analog of N-methyltryptamine (NMT). It was first isolated from Phalaris arundinacea. It has also been synthesized by Alexander Shulgin and reported in his book TiHKAL. Like other members of the N-methyltryptamine family of compounds, 5-MeO-NMT is believed to produce few or no psychedelic effects, although very little data exists about its pharmacological properties or toxicity.

<i>N</i>-Methylphenethylamine Chemical compound

N-Methylphenethylamine (NMPEA) is a naturally occurring trace amine neuromodulator in humans that is derived from the trace amine, phenethylamine (PEA). It has been detected in human urine and is produced by phenylethanolamine N-methyltransferase with phenethylamine as a substrate, which significantly increases PEA's effects. PEA breaks down into Phenylacetaldehyde which is further broken down into Phenylacetic acid by Monoamine oxidase. When this is inhibited by Monoamine oxidase inhibitors, it allows more of the PEA to be metabolized into nymphetamine (NMPEA) and not wasted on the weaker inactive metabolites.

<span class="mw-page-title-main">Alpha,N-DMT</span> Chemical compound

Alpha,N-DMT, or α,N-dimethyltryptamine, is a lesser-known psychedelic drug. It is the α,N-dimethyl analog of DMT. α,N-DMT was first synthesized by Alexander Shulgin. In his book TiHKAL, Shulgin lists the dosage as 50-100 mg, and the duration as 6–8 hours. α,N-DMT causes an unpleasant body load. Very little data exists about the pharmacological properties, metabolism, and toxicity of α,N-DMT. α,N-DMT is known to be a potent monoamine oxidase inhibitor

Amine <i>N</i>-methyltransferase Class of enzymes

In enzymology, an amine N-methyltransferase is an enzyme that is ubiquitously present in non-neural tissues and that catalyzes the N-methylation of tryptamine and structurally related compounds.

<i>N</i>-Methyltyramine Chemical compound

N-Methyltyramine (NMT), also known as 4-hydroxy-N-methylphenethylamine, is a human trace amine and natural phenethylamine alkaloid found in a variety of plants. As the name implies, it is the N-methyl analog of tyramine, which is a well-known biogenic trace amine with which NMT shares many pharmacological properties. Biosynthetically, NMT is produced by the N-methylation of tyramine via the action of the enzyme phenylethanolamine N-methyltransferase in humans and tyramine N-methyltransferase in plants.

<span class="mw-page-title-main">Substituted tryptamine</span> Class of indoles

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 (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.

<span class="mw-page-title-main">Lespedamine</span> Chemical compound

Lespedamine is an indole alkaloid and substituted tryptamine present in the plant Lespedeza bicolor. The alkaloid bears a close structural resemblance to the psychedelic alkaloid dimethyltryptamine and was speculated to have psychoactivity by Alexander Shulgin. No reports on lespedamine's biological activity have been published.

<i>O</i>-Acetylbufotenine Chemical compound

O-Acetylbufotenine is a tryptamine derivative which produces psychedelic-appropriate responding in animal studies. It is an acylated derivative of bufotenine with higher lipophilicity that allows it to cross the blood–brain barrier; once inside the brain, it is metabolised to bufotenine. It also acts directly as an agonist at 5-HT1A and 5-HT1D receptors.

<span class="mw-page-title-main">2-HO-NMT</span> Chemical compound

2-Hydroxy-N-methyltryptamine (2-HO-NMT) is a tryptamine and is the 2-hydroxy analog of N-methyltryptamine (NMT). It is briefly mentioned in Alexander Shulgin's book TiHKAL under the DMT entry and is stated to be found in Desmanthus illinoensis.

<span class="mw-page-title-main">5,6-Dibromo-DMT</span> Chemical compound

5,6-Dibromo-DMT is a substituted tryptamine alkaloid found in some marine sponges. It is briefly mentioned in Alexander Shulgin's book TiHKAL under the DMT entry and is stated to be found, along with other tryptamines, in Smenospongia aurea and other sponges.


  1. Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family". Trends in Pharmacological Sciences. 26 (5): 274–281. doi:10.1016/j.tips.2005.03.007. PMID   15860375.
  2. Burchett SA, Hicks TP (August 2006). "The mysterious trace amines: protean neuromodulators of synaptic transmission in mammalian brain". Progress in Neurobiology. 79 (5–6): 223–246. doi:10.1016/j.pneurobio.2006.07.003. PMID   16962229. S2CID   10272684.
  3. Forsström T, Tuominen J, Karkkäinen J (2001). "Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS". Scandinavian Journal of Clinical and Laboratory Investigation. 61 (7): 547–56. doi:10.1080/003655101753218319. PMID   11763413. S2CID   218987277.
  4. 1 2 Foye WO, Lemke TL, Williams DA (2002). "Hallucinogens, Stimulatants, and Drugs of Abuse". Foye's Principles of Medicinal Chemistry (5th ed.). p. 439. ISBN   9780683307375.
  5. Shulgin A, Shulgin A (1997). TIKHAL. Berkeley: Transform Press.
  6. Nen - lecture presented EGA conference, Victoria, Australia 4/12/2011; and Breaking Conventions, London 12/7/2013.
  7. https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf [ bare URL PDF ]