2,N,N-TMT

Last updated
2,N,N-TMT
2-Me-DMT.svg
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
  • (2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C13H18N2
Molar mass 202.301 g·mol−1
3D model (JSmol)
  • Cc1c(c2ccccc2[nH]1)CCN(C)C
  • InChI=1S/C13H18N2/c1-10-11(8-9-15(2)3)12-6-4-5-7-13(12)14-10/h4-7,14H,8-9H2,1-3H3
  • Key:NDGCOWDSLVNLGE-UHFFFAOYSA-N
   (verify)

2,N,N-trimethyltryptamine, 2,N,N-TMT, or 2-Me-DMT is a tryptamine derivative that is a psychedelic drug. It was invented by Alexander Shulgin and reported in his book TiHKAL (#34). [1] It is claimed to show psychoactive effects at a dosage of 50–100 mg orally, but these are relatively mild compared to other similar drugs, suggesting that while the 2-methyl group has blocked the binding of metabolic enzymes, it is also interfering with binding to the 5HT2A receptor target that mediates the hallucinogenic effects of these drugs.

Contents

Sweden's public health agency suggested classifying 2-Me-DMT as a hazardous substance, on May 15, 2019. [2]

See also

Related Research Articles

<i>alpha</i>-Methyltryptamine Chemical compound

α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by workers at Upjohn in the 1960s, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.

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

N,N-Dipropyltryptamine (DPT) is a psychedelic entheogen belonging to the tryptamine family. Use as a designer drug has been documented by law enforcement officials since as early as 1968. However, potential therapeutic use was not investigated until the 1970s. It is found either as a crystalline hydrochloride salt or as an oily or crystalline base. It has not been found to occur endogenously. It is a close structural homologue of dimethyltryptamine and diethyltryptamine.

<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">Bufotenin</span> Psychedelic drug found in toads, mushrooms and plants

Bufotenin is a tryptamine derivative, more specifically, a DMT analog, related to the neurotransmitter serotonin. It is an alkaloid found in some species of mushrooms, plants and toads, especially the skin.

<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">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-HO-MiPT</span> Chemical compound

4-HO-MiPT is a synthetic substituted aromatic compound and a lesser-known psychedelic tryptamine. It is thought to be a serotonergic psychedelic, similar to magic mushrooms, LSD and mescaline. Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine psilocin, which is the primary psychoactive chemical in magic mushrooms.

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

N-Methyl-N-isopropyltryptamine (MiPT) is a psychedelic tryptamine, closely related to DMT, DiPT and Miprocin.

<span class="mw-page-title-main">5,N,N-TMT</span> Chemical compound

5,N,N-trimethyltryptamine is a tryptamine derivative that is a psychedelic drug. It was first made in 1958 by E. H. Young. In animal experiments it was found to be in between DMT and 5-MeO-DMT in potency which would suggest an active dosage for humans in the 20–60 mg range. Human psychoactivity for this compound has been claimed in reports on websites such as Erowid but has not been independently confirmed.

<span class="mw-page-title-main">5-MeO-2-TMT</span> Chemical compound

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.

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

N,N-Dibutyltryptamine (DBT) is a psychedelic drug belonging to the tryptamine family. It is found either as its crystalline hydrochloride salt or as an oily or crystalline base. DBT was first synthesized by the chemist Alexander Shulgin and reported in his book TiHKAL . Shulgin did not test DBT himself, but reports a human dosage of "1 mg/kg i.m." being active, but less so than DMT or DET. This suggests that an active dosage of DBT will be in the 100 mg range. This compound has been sold as a "research chemical" and has been confirmed to be an active hallucinogen although somewhat weaker than other similar tryptamine derivatives. It produces a head-twitch response in mice.

<span class="mw-page-title-main">4-MeO-MiPT</span> Chemical compound

4-MeO-MiPT, or 4-methoxy-N-methyl-N-isopropyltryptamine, is a lesser-known psychedelic drug. It is the 4-methoxy analog of MiPT. 4-MeO-MiPT was first synthesized by Alexander Shulgin and is mentioned in his book TiHKAL. Subsequent testing by Shulgin on human test subjects showed the effective dose as 20-30 mg ; the onset time between ingestion and the first noticeable effects was 45-60 min, with sensations lasting between 2-2.5 hours. The sensation were significantly milder than those of 4-HO-MiPT, with 4-MeO-MiPT producing erotic-enhancing effects, and few of the visuals common with tryptamines. Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-MeO-MiPT.

<span class="mw-page-title-main">5-MeO-pyr-T</span> 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.

<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">5,6-MDO-DMT</span> Chemical compound

5,6-MDO-DMT, or 5,6-methylenedioxy-N,N-dimethyltryptamine, is a lesser-known psychedelic drug. It is the 5,6-methylenedioxy analog of DMT. 5,6-MDO-DMT was first synthesized by Alexander Shulgin. In his book TiHKAL, 5,6-MDO-DMT produces no noticeable psychoactive effects, although it was only tested up to a dose of 5 mg. Very little data exists about the pharmacological properties, metabolism, and toxicity of 5,6-MDO-DMT.

<span class="mw-page-title-main">4,5-MDO-DMT</span> Chemical compound

4,5-MDO-DMT, or 4,5-methylenedioxy-N,N-dimethyltryptamine, is a lesser-known psychedelic drug. It is the 4,5-methylenedioxy analog of DMT. 4,5-MDO-DMT was first synthesized by Alexander Shulgin, though in his book TiHKAL it was not tested to determine its psychoactive effects. 4,5-MDO-DMT has been the subject of limited subsequent testing; with behavioral disruption studies performed in male rats indicating that its hallucinogenic potency is less than that of 4,5-MDO-DiPT but greater than that of 5,6-MDO-DiPT.

<span class="mw-page-title-main">4-HO-αMT</span> Chemical compound

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.

5-Methoxy-7,<i>N</i>,<i>N</i>-trimethyltryptamine Chemical compound

5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7,N,N-TMT, 5-MeO-7-TMT), is a tryptamine derivative which acts as an agonist at the 5-HT2 serotonin receptors. In animal tests, both 7,N,N-TMT and 5-MeO-7,N,N-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT and 5-MeO-DMT, but compounds with larger 7-position substituents such as 7-ethyl-DMT and 7-bromo-DMT did not produce psychedelic-appropriate responding despite high 5-HT2 receptor binding affinity, suggesting these may be antagonists or weak partial agonists for the 5-HT2 receptors. The related compound 7-MeO-MiPT (cf. 5-MeO-MiPT) was also found to be inactive, suggesting that the 7-position has poor tolerance for bulky groups at this position, at least if agonist activity is desired.

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

5-MeO EiPT is a psychedelic of the tryptamine class that has been sold online as a designer drug.

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

5-MeO-MALT (5-methoxy-N-methyl-N-allyltryptamine) is a lesser-known psychedelic drug that is closely related to 5-MeO-DALT and has been sold online as a designer drug.

References

  1. Erowid Online Books : "TIHKAL" - #34 2-ME-DMT
  2. "Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 15 May 2019. Archived from the original on 20 October 2021. Retrieved 11 November 2019.