5-MeO-T-NB3OMe

5-MeO-T-NB3OMe, or 5MT-NB3OMe, also known as N-(3-methoxybenzyl)-5-methoxytryptamine, is a serotonin receptor modulator and psychedelic drug of the tryptamine, 5-methoxytryptamine, and N-benzyltryptamine families related to the 25-NB (NBOMe) psychedelics.^[1][2][3][4] It is a positional isomer of 5-MeO-T-NBOMe (5-MeO-T-NB2OMe).^[2]

Other names5MT-NB3OMe; NB3MeO-5-MeO-T; 5-MeO-T-NB3MeO; 5-MeO-NB3OMeT; N-(3-Methoxybenzyl)-5-methoxytryptamine

Drug classSerotonin receptor modulator; Serotonin 5-HT_2A receptor agonist; Serotonergic psychedelic; Hallucinogen

ATC code

• None

CAS Number

• 1648553-42-7

Quick facts Clinical data, Other names ...

5-MeO-T-NB3OMe

Clinical data
Other names	5MT-NB3OMe; NB3MeO-5-MeO-T; 5-MeO-T-NB3MeO; 5-MeO-NB3OMeT; N-(3-Methoxybenzyl)-5-methoxytryptamine
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name 2-(5-methoxy-1H-indol-3-yl)-N-[(3-methoxyphenyl)methyl]ethanamine
CAS Number	1648553-42-7
PubChem CID	172915172
ChemSpider	128484569
Chemical and physical data
Formula	C19H22N2O2
Molar mass	310.397 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC2=C(C=C1)NC=C2CCNCC3=CC(=CC=C3)OC
InChI InChI=1S/C19H22N2O2/c1-22-16-5-3-4-14(10-16)12-20-9-8-15-13-21-19-7-6-17(23-2)11-18(15)19/h3-7,10-11,13,20-21H,8-9,12H2,1-2H3 Key:CJLDIVRTIQMENX-UHFFFAOYSA-N

Close

The drug shows affinity for many serotonin receptors and acts as an agonist of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[4] It had similar affinity and activational potency at the human serotonin 5-HT_2A receptor as 5-MeO-T-NBOMe.^[4] In addition, the drug had around 10-fold lower affinity for the human serotonin 5-HT_2A receptor as 25I-NBOMe (25I-NB2OMe) but showed similar activational potency at this receptor as 25I-NBOMe.^[4] 5-MeO-T-NB3OMe produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.^[2][4] It had similar potency in this test as 5-MeO-T-NBOMe and 25I-NB3OMe, but showed dramatically or 42- to 45-fold lower potency than 25I-NBOMe.^[2][4]

The chemical synthesis of 5-MeO-T-NB3OMe has been described.^[4] Various analogues of 5-MeO-T-NB3OMe besides 5-MeO-T-NBOMe have also been described.^[2][4][5][6]

5-MeO-T-NB3OMe was first described in the scientific literature by David E. Nichols and colleagues in 2015.^[1][2][3][4] It is not a controlled substance in Canada as of 2025.^[7] It is also not an explicitly controlled substance in the United States,^[8] but it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.