N-Methyltryptamine

Last updated
N-Methyltryptamine
NMT structure.svg
Legal status
Legal status
Identifiers
  • 2-(1H-Indol-3-yl)-N-methylethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.462 OOjs UI icon edit-ltr-progressive.svg
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
  • Key:NCIKQJBVUNUXLW-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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 ]

Contents

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]

Legality

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

<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. DMT 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, bufo, 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">Diisopropyltryptamine</span> Chemical compound

Diisopropyltryptamine is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily aural.

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

DET, also known under its chemical name N,N-diethyltryptamine and as T-9, is a psychedelic drug closely related to DMT and 4-HO-DET. However, despite its structural similarity to DMT, its activity is induced by an oral dose of around 50–100 mg, without the aid of MAO inhibitors, and the effects last for about 2–4 hours.

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

Harmaline is a fluorescent indole alkaloid from the group of harmala alkaloids and beta-carbolines. It is the partly hydrogenated form of harmine.

<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.

<span class="mw-page-title-main">4-Hydroxy-5-methoxydimethyltryptamine</span> Chemical compound

4-Hydroxy-5-methoxydimethyltryptamine, also known as 4-HO-5-MeO-DMT or psilomethoxin, is a hypothetical novel psychedelic drug. It is the 4-hydroxy counterpart of 5-MeO-DMT, or the 5-methoxy counterpart of psilocin.

α,<i>N</i>,<i>N</i>-Trimethyltryptamine Psychoactive drug

α,N,N-Trimethyltryptamine is a psychoactive drug of the tryptamine chemical class which acts as a psychedelic hallucinogen. It is similar in structure to the other psychedelics of the tryptamine class such as dimethyltryptamine (DMT) and α-methyltryptamine (α-MT).

<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-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.

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

Amine N-methyltransferase, also called indolethylamine N-methyltransferase, and thioether S-methyltransferase, is an enzyme that is ubiquitously present in non-neural tissues and catalyzes the N-methylation of tryptamine and structurally related compounds. More recently, it was discovered that this enzyme can also catalyze the methylation of thioether and selenoether compounds, although the physiological significance of this biotransformation is not yet known.

<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">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.

References

  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. "Orange Book - List of Controlled Substances and Regulated Chemicals" (PDF). U.S. Department of Justice Diversion Control Division. August 2023. Archived (PDF) from the original on September 6, 2023.