N-Methyltryptamine

Template:Short description Template:Template other{{Infobox drug/maintenance categoriesTemplate:Yesno | drug_name = N-Methyltryptamine | INN = | _drugtype =

| _has_physiological_data= | _has_gene_therapy=

| vaccine_type= | mab_type= | _number_of_combo_chemicals= | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=11142CNCCc1c[nH]c2ccccc121S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3NCIKQJBVUNUXLW-UHFFFAOYSA-NTemplate:StdinchiciteTemplate:Stdinchicite8789 | _combo_data= | _physiological_data= | _clinical_data=

| _legal_data=Schedule I (isomer of AMT)

| _other_data=2-(1H-Indol-3-yl)-N-methylethan-1-amine

| _image_0_or_2 = NMT structure.svg | _image_LR =

| _datapage = N-Methyltryptamine (data page) | _vaccine_target=_type_not_vaccine | _legal_all=Schedule I (isomer of AMT) | _ATC_prefix_supplemental= | _has_EMA_link = | CAS_number=61-49-4 | PubChem=6088 | ChemSpiderID=5863 | ChEBI=28136 | ChEMBL=348588 | DrugBank= | KEGG=C06213 | _hasInChI_or_Key=yes | UNII=6FRL4L3Z7V | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =

| _countSecondIDs= | _countIndexlabels= | _trackListSortletter= |QID = |QID2 = |Verifiedfields=verified |Watchedfields=verified |verifiedrevid=464372446}}

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.

Effects

Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.

Per Roger W. Brimblecombe and colleagues, NMT is inactive in humans, with few details provided. On the other hand, according to Alexander Shulgin and 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).

Pharmacology

NMT is known to act as a potent serotonin 5-HT_2A receptor full agonist (EC₅₀Tooltip half-maximal effective concentration = 50.7nM; E_maxTooltip maximal efficacy = 96%). It has been reported to be inactive in activating the β-arrestin pathway of the receptor and hence appears to be a biased agonist of the serotonin 5-HT_2A receptor. In contrast to the serotonin 5-HT_2A receptor, the drug is not an agonist of the serotonin 5-HT_1A receptor.

In addition to its serotonin 5-HT_2A receptor agonism, NMT is a potent serotonin releasing agent (EC₅₀ = 22.4nM). It also releases dopamine and norepinephrine much more weakly (EC₅₀ = 321nM and 733nM, respectively; 14- and 33-fold less than for serotonin, respectively).

Society and culture

Legal status

In the United States NMT is considered a schedule 1 controlled substance as an positional isomer of Alpha-methyltryptamine (AMT).

See also

• N-Ethyltryptamine (NET)
• N,N,-Dimethyltryptamine (DMT)
• Acacia confusa (a natural source of NMT, with other tryptamines, 1.63%. Buchanan et al. 2007)
• Acacia obtusifolia (NMT up to 2/3 alkaloid content)
• Acacia simplicifolia (synon. A. simplex) (1.44% NMT in bark, 0.29% twigs, Pouet et al. 1976)
• Desmanthus illinoensis (NMT major component seasonally)

External links

• NMT - Isomer Design
• NMT - TiHKAL - Erowid
• NMT - TiHKAL - Isomer Design
• N-Methyltryptamine (NMT) - Trout's Notes