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N-Methyltryptamine
Chemical compound
Chemical compound
| Field | Value | ||
|---|---|---|---|
| Verifiedfields | verified | ||
| Watchedfields | verified | ||
| verifiedrevid | 464372446 | ||
| drug_name | *N*-Methyltryptamine | ||
| image | NMT structure.svg | ||
| image_class | skin-invert-image | ||
| width | 200px | ||
| image2 | NMT 3D.png | ||
| image_class2 | bg-transparent | ||
| width2 | 200px | ||
| routes_of_administration | Smoking, oral (with an ) | ||
| class | Non-selective serotonin receptor agonist; Serotonin [5-HT2A receptor](5-ht2a-receptor) agonist; Serotonergic psychedelic; Hallucinogen | ||
| duration_of_action | Seconds to minutes | ||
| CAS_number_Ref | |||
| legal_US | Schedule I (isomer of AMT) | ||
| CAS_number | 61-49-4 | ||
| UNII_Ref | |||
| UNII | 6FRL4L3Z7V | ||
| PubChem | 6088 | ||
| ChemSpiderID_Ref | |||
| ChemSpiderID | 5863 | ||
| KEGG_Ref | |||
| KEGG | C06213 | ||
| ChEBI_Ref | |||
| ChEBI | 28136 | ||
| ChEMBL_Ref | |||
| ChEMBL | 348588 | ||
| synonyms | NMT; Methyltryptamine; *N*-MT; Monomethyltryptamine; Dipterine; PAL-152; PAL152 | ||
| IUPAC_name | 2-(1*H*-indol-3-yl)-*N*-methylethan-1-amine | ||
| C | 11 | H = 14 | N = 2 |
| SMILES | CNCCc1c[nH]c2ccccc12 | ||
| StdInChI_Ref | |||
| StdInChI | 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 | ||
| StdInChIKey_Ref | |||
| StdInChIKey | NCIKQJBVUNUXLW-UHFFFAOYSA-N | ||
| melting_point | 87 | ||
| melting_high | 89 |
| elimination_half-life =
N-Methyltryptamine (NMT), also known as monomethyltryptamine, is a chemical compound of the tryptamine family and a naturally occurring compound found in the human body and certain plants.
It is biosynthesized in humans from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase. It is a known 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).
NMT acts as a serotonin receptor agonist and serotonin releasing agent and is said to produce hallucinogenic effects in humans.
NMT was encountered as a novel designer drug by 2014, though it is not commonly used itself due to its weak effects.
Use and effects
Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.
According to Roger W. Brimblecombe and colleagues, NMT is inactive in humans, with few details provided. On the other hand, according to reports given to Alexander Shulgin and by others, NMT is active via non-oral routes. It has been said to produce psychedelic effects at doses of 50 to 120mg by smoking or vaporization, with a duration of seconds to minutes. Based on preliminary reports, NMT is reported to produce visuals, but its effects are described as primarily spatial in nature, among other effects.
NMT has also been reported to be orally active in combination with a monoamine oxidase inhibitor (MAOI).
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| [5-HT1A](5-ht1a-receptor) | IA |
| [5-HT2A](5-ht2a-receptor) | 51 () |
| 96% () | |
| SERT | 22a (EC50) |
| 733a (EC50) | |
| 321a (EC50) | |
| **Notes:** The smaller the value, the more avidly the drug interacts with the site. **Footnotes:** a = Neurotransmitter release. **Sources: ** |
NMT is known to act as a potent serotonin 5-HT2A receptor full agonist. It has been reported to be inactive in activating the β-arrestin2 pathway of the receptor and hence appears to be a biased agonist of the serotonin 5-HT2A receptor. The drug does not seem to be an agonist of the serotonin 5-HT1A receptor.
In addition to its serotonin 5-HT2A receptor agonism, NMT is a potent serotonin releasing agent. It also releases dopamine and norepinephrine much more weakly (14- and 33-fold less than for serotonin, respectively).
NMT has also been evaluated for binding affinity at the sigma σ1 and sigma σ2 receptors. It's affinity towards both sigma receptors is intermediate between the unmethylated tryptamine and the fully dimethylated DMT.
Pharmacokinetics
NMT undergoes oxidative deamination by monoamine oxidase (MAO), particularly MAO-A, which preferentially metabolizes serotonin and tryptamine derivatives. The intermediate methylation state of NMT makes it a substrate for further N-methylation to DMT by amine N-methyltransferase (INMT).
Chemistry
Synthesis
The chemical synthesis of NMT has been described.
Analogues
Analogues of NMT include N-ethyltryptamine (NET), methylethyltryptamine (MET), and dimethyltryptamine (DMT), among others.
Natural occurrence
NMT is naturally occurring in Acacia species like Acacia confusa (1.63%; Buchanan et al., 2007), Acacia obtusifolia (up to two-thirds of total alkaloid content), and Acacia simplicifolia (A. simplex; 1.44% in bark, 0.29% twigs; Pouet et al., 1976) and Desmanthus illinoensis (major component seasonally).
History
NMT was encountered as a novel designer drug by 2014.
Society and culture
Legal status
Canada
NMT is not a controlled substance in Canada.
United States
In the United States, NMT is considered a schedule 1 controlled substance as an positional isomer of α-methyltryptamine (AMT).
References
References
- (May 2005). "A renaissance in trace amines inspired by a novel GPCR family". Trends in Pharmacological Sciences.
- (August 2006). "The mysterious trace amines: protean neuromodulators of synaptic transmission in mammalian brain". Progress in Neurobiology.
- (2001). "Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS". Scandinavian Journal of Clinical and Laboratory Investigation.
- Ott, Jonathan. (1996). "Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History". Natural Products Company.
- "NMT (N-Метилтриптамин)".
- (2002). "Foye's Principles of Medicinal Chemistry". Lippincott Williams & Wilkins.
- (1975). "Hallucinogenic Agents". Wright-Scientechnica.
- (1997). "[[TiHKAL: The Continuation]]". Transform Press.
- Nen. (4 December 2011). "Entheogenic effects of NMT from Acacia".
- Nen. (13 July 2013). "NMT: A Spatial Hallucinogen With Therapeutic Applications".
- (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl).
- (October 2010). "Serotonin, But Not N-Methyltryptamines, Activates the Serotonin 2A Receptor Via a β-Arrestin2/Src/Akt Signaling Complex In Vivo". The Journal of Neuroscience.
- (February 2009). "The Hallucinogen N,N -Dimethyltryptamine (DMT) Is an Endogenous Sigma-1 Receptor Regulator". Science.
- (5 December 2025). "Controlled Drugs and Substances Act".
- (August 2023). "Orange Book - List of Controlled Substances and Regulated Chemicals".
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