5-MeO-NMT

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5-MeO-NMT
5-MeO-NMT.png
Names
Preferred IUPAC name
2-(5-Methoxy-1H-indol-3-yl)-N-methylethan-1-amine
Other names
5-Methoxy-N-methyltryptamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C12H16N2O/c1-13-6-5-9-8-14-12-4-3-10(15-2)7-11(9)12/h3-4,7-8,13-14H,5-6H2,1-2H3 Yes check.svgY
    Key: NFDDCRIHMZGWBP-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H16N2O/c1-13-6-5-9-8-14-12-4-3-10(15-2)7-11(9)12/h3-4,7-8,13-14H,5-6H2,1-2H3
    Key: NFDDCRIHMZGWBP-UHFFFAOYAI
  • CNCCC1=CNC2=CC=C(C=C21)OC
Properties
C12H16N2O
Molar mass 204.273 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 (reed canary grass). [1] It has also been synthesized by Alexander Shulgin and reported in his book TiHKAL . [2] 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.

See also

Related Research Articles

NMT may refer to:

<i>Anadenanthera peregrina</i> Species of plant

Anadenanthera peregrina, also known as yopo, jopo, cohoba, parica or calcium tree, is a perennial tree of the genus Anadenanthera native to the Caribbean and South America. It grows up to 20 m (66 ft) tall, and has a horny bark. Its flowers grow in small, pale yellow to white spherical clusters resembling Acacia inflorescences. It is an entheogen which has been used in healing ceremonies and rituals for thousands of years in northern South America and the Caribbean.

<i>Phalaris arundinacea</i> Species of Plant

Phalaris arundinacea, or reed canary grass, is a tall, perennial bunchgrass that commonly forms extensive single-species stands along the margins of lakes and streams and in wet open areas, with a wide distribution in Europe, Asia, northern Africa and North America. Other common names for the plant include gardener's-garters in English, alpiste roseau in French, rohrglanzgras in German, kusa-yoshi in Japanese, caniço-malhado in Portuguese, and hierba cinta and pasto cinto in Spanish.

5-Methoxy-<i>N</i>,<i>N</i>-diisopropyltryptamine

5-Methoxy-N,N-diisopropyltryptamine is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT).

5-MeO-aMT

5-MeO-aMT or 5-methoxy-α-methyltryptamine, α,O-Dimethylserotonin (Alpha-O) is a potent psychedelic tryptamine. It is soluble in ethanol.

<i>N</i>-Ethyltryptamine

N-Ethyltryptamine (NET), or merely ethyltryptamine, is a tryptamine that is structurally related to N-methyltryptamine (NMT) and the psychedelic drugs N,N-dimethyltryptamine (DMT) and N,N-diethyltryptamine (DET).

<i>Phalaris</i> (plant) genus of flowering plant in the grass family Poaceae

Phalaris is a genus of grasses. Various species of Phalaris grow on every continent except Antarctica. They can be found in a broad range of habitats from below sea level to thousands of feet above sea level and from wet marshy areas to dry places. P. arundinacea and P. aquatica are sometimes invasive species in wetlands.

<i>Anadenanthera</i> Genus of plants

Anadenanthera is a genus of South American trees in the Legume family, Fabaceae. The genus contains two to four species, including A. colubrina and A. peregrina. These trees respectively are known to the western world primarily as sources of the hallucinogenic snuffs Vilca/Cebil and Yopo/Cohoba.

5-MeO-MiPT

5-MeO-MiPT is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.

5-MeO-DPT

5-MeO-DPT, is a psychedelic and entheogenic drug.

<i>N</i>-Methyltryptamine

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. It is a common component in human urine. 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).

5-MeO-AET

5-Methoxy-alpha-ethyltryptamine (5-MeO-α-ET) is a psychoactive drug and member of the tryptamine chemical class. It produces psychedelic, entactogenic, and stimulant effects.

4-Hydroxy-5-methoxydimethyltryptamine

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

5-MeO-2-TMT

5-Methoxy-2,N,N-trimethyltryptamine is a psychoactive drug of the tryptamine chemical class which acts as a psychedelic. It was first synthesized by Alexander Shulgin and reported in his book TiHKAL. 5-MeO-TMT is claimed to show psychoactive effects at a dosage of 75–150 mg orally, but these are relatively mild compared to those of other similar compounds. This suggests that while the methyl group on the 2-position of the molecule has impaired the binding of metabolic enzymes like monoamine oxidase (MAO), it is also interfering with binding to and/or activation of the serotonin 5-HT2A receptor, the target responsible for mediating the hallucinogenic effects of such compounds.

5-MeO-pyr-T Chemical compound

5-MeO-pyr-T (5-methoxy-N,N-tetramethylenetryptamine) is a lesser-known psychedelic drug. It is the 5-methoxy analog of pyr-T. 5-MeO-pyr-T was first synthesized by Hunt & Brimblecombe, who credited S. Mitzal for characterization of chemical properties. Later human tests were reported by Alexander Shulgin, in his book TiHKAL. An oral dosage of 0.5 to 2 mg, and an inhaled dosage of 2–3 mg are reported. 5-MeO-pyr-T causes varying reactions, such as amnesia, tinnitus, vomiting, and a 5-MeO-DMT-like rushing sensation. At the highest dosage reported in TiHKAL, the subject describes awakening from an apparent fugue state during which they were wandering the streets, with complete amnesia upon awakening.

5-MeO-MPMI

5-MeO-MPMI is a tryptamine derivative that is a psychedelic drug. It was first developed by the team led by JE Macor in 1992, and subsequently investigated by the team led by David Nichols from Purdue University in the late 1990s. This compound produces psychedelic-appropriate responding in animal tests with a similar potency to the amphetamine-derived psychedelic DOI, and has two enantiomers, with only the (R)-enantiomer being active.

4-HO-αMT

4-Hydroxy-α-methyltryptamine (4-HO-αMT) is a psychedelic drug of the tryptamine class. It is a close structural analogue of α-methyltryptamine (αMT) and produces similar effects to it, but with exacerbated side effects similarly to 5-MeO-αMT. Alexander Shulgin describes 4-HO-αMT briefly in his book TiHKAL:

The 4-hydroxy analogue of αMT has been looked at in human subjects. It is reported to be markedly visual in its effects, with some subjects reporting dizziness and a depressed feeling. There were, however, several toxic signs at doses of 15 to 20 milligrams orally, including abdominal pain, tachycardia, increased blood pressure and, with several people, headache and diarrhea.

Lespedamine 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.

References

  1. Wilkinson, S. (1958). "428. 5-Methoxy-N-methyltryptamine: a new indole alkaloid from Phalaris arundinacea L.". Journal of the Chemical Society (Resumed): 2079. doi:10.1039/jr9580002079.
  2. 5-MeO-NMT Entry in TIHKAL