5-MeO-NBpBrT

5-MeO-NBpBrT
Clinical data
Other names	5-Methoxy-N-(4-bromobenzyl)tryptamine
ATC code	None;
Identifiers
	IUPAC name N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine;
CAS Number	155639-13-7 ;
PubChem CID	5124753;
ChemSpider	4299315 ;
UNII	UG43REN7BR;
ChEMBL	ChEMBL57427 ;
CompTox Dashboard (EPA)	DTXSID901029953 ;
Chemical and physical data
Formula	C18H19BrN2O
Molar mass	359.267 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES BrC1=CC=C(CNCCC2=CNC3=CC=C(OC)C=C23)C=C1;
	InChI InChI=1S/C18H19BrN2O/c1-22-16-6-7-18-17(10-16)14(12-21-18)8-9-20-11-13-2-4-15(19)5-3-13/h2-7,10,12,20-21H,8-9,11H2,1H3 ; Key:XHLOUFPZLUULGI-UHFFFAOYSA-N ;
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5-MeO-NBpBrT, also known as 5-methoxy-N-(4-bromobenzyl)tryptamine, is an N-substituted member of the 5-methoxytryptamine family of compounds. Like other such compounds, it acts as an antagonist for the serotonin 5-HT_2A receptor, with a claimed 100-fold selectivity over the closely related serotonin 5-HT_2C receptor.^[1] While N-benzyl substitution of psychedelic phenethylamines often results in potent serotonin 5-HT_2A agonists, it had been thought that N-benzyltryptamines show much lower efficacy and are either very weak partial agonists or antagonists at the serotonin 5-HT_2A receptor,^[2]^[3] though more recent research has shown stronger agonist activity for 3-substituted benzyl derivatives.^[4] Extending the benzyl group to a substituted phenethyl can also recover agonist activity in certain cases.^[5]