5-MeO-NMT

5-MeO-NMT, also known as 5-methoxy-N-methyltryptamine, is an organic chemical compound, being the 5-methoxy analogue of N-methyltryptamine (NMT). It was first isolated from Phalaris arundinacea (reed canary grass) and also occurs in other species such as Virola species and Bufo alvarius skin.^[1][2] The compound has been synthesized by Alexander Shulgin and reported in his book TiHKAL.^[1]

5-MeO-NMT

Names
Preferred IUPAC name 2-(5-Methoxy-1H-indol-3-yl)-N-methylethan-1-amine
Other names 5-Methoxy-N-methyltryptamine
Identifiers
CAS Number	2009-03-2 (freebase) Y 2426-68-8 (hydrochloride) Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:189635 Y
ChEMBL	ChEMBL58579 Y
ChemSpider	15360 Y
PubChem CID	16184
UNII	YBO217L5YV (freebase) Y 3390M5391J (hydrochloride) Y
CompTox Dashboard (EPA)	DTXSID40173909
InChI 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 Y Key: NFDDCRIHMZGWBP-UHFFFAOYSA-N Y 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
SMILES CNCCC1=CNC2=CC=C(C=C21)OC
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

Use and effects

Shulgin included 5-MeO-NMT as an entry in TiHKAL.^[1] However, he does not appear to have tried it and states that the dosage and duration of the compound are unknown.^[1] In any case, Shulgin stated that it would be expected to be rapidly metabolized by monoamine oxidase and that it would likely only be active parenterally.^[1]

Pharmacology

5-MeO-NMT is a potent agonist of the serotonin 5-HT_1A, 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[3] It is a full agonist or near-full agonist of all of these receptors except for the serotonin 5-HT_2A receptor, where it is a partial agonist.^[3] The drug is also a very weak serotonin releasing agent.^[3][4]

5-MeO-NMT does not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.^[3] On the other hand, it does induce serotonin 5-HT_1A receptor-mediated hypothermia and hypolocomotion.^[3] Earlier reports had stated that 5-MeO-NMT and its N-demethylated analogue 5-methoxytryptamine were inactive, but this proved not to be the case.^[5]

Chemistry

Notable analogues of 5-MeO-NMT include NMT, 5-MeO-NET, 5-MeO-NiPT, norpsilocin (4-HO-NMT), baeocystin (4-PO-NMT), 4-HO-NALT, and 5-MeO-NBpBrT, among others.^[3][4] 5-MeO-NMT is the N-monodemethylated analogue of 5-MeO-DMT.

Society and culture

Legal status

United States

In the United States, this substance is a Schedule 1 analogue of bufotenin.^{[citation needed]}