NBOMe-escaline

NBOMe-escaline, also known as escaline-NBOMe or as N-(2-methoxybenzyl)-4-ethoxy-3,5-dimethoxyphenethylamine, is a serotonin receptor agonist and putative psychedelic drug of the phenethylamine, scaline, and N-benzylphenethylamine (NBOMe) families.^[1][2] It is the N-(2-methoxybenzyl) derivative of escaline.^[1][2]

NBOMe-escaline

Clinical data
Other names	Escaline-NBOMe; Esc-NBOMe; N-(2-Methoxybenzyl)-4-ethoxy-3,5-dimethoxyphenethylamine
Drug class	Serotonin 5-HT2A receptor partial agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name 2-(4-ethoxy-3,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number	1027079-85-1
PubChem CID	10405293
ChemSpider	8580731
Chemical and physical data
Formula	C20H27NO4
Molar mass	345.439 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCOC1=C(C=C(C=C1OC)CCNCC2=CC=CC=C2OC)OC
InChI InChI=1S/C20H27NO4/c1-5-25-20-18(23-3)12-15(13-19(20)24-4)10-11-21-14-16-8-6-7-9-17(16)22-2/h6-9,12-13,21H,5,10-11,14H2,1-4H3 Key:VIFKVOUQWKUXLL-UHFFFAOYSA-N

The drug acts as a potent serotonin 5-HT_2A receptor partial agonist, with an affinity (A₂) of 0.537 nM, an activational potency (K_P) of 7.08 nM, and an intrinsic activity (E_maxTooltip maximal efficacy) of 48%.^[1][2] As a serotonin 5-HT_2A receptor agonist in vitro, it was 7-fold more potent than NBOMe-mescaline, 50-fold more potent than escaline, and 476-fold more potent than mescaline.^[1]

NBOMe-escaline was first described in the scientific literature by Heinz Pertz and colleagues by 1999.^[1][2] Along with NBOMe-mescaline, it was one of the first psychedelic N-benzylphenethylamines to be discovered, slightly preceding the publication of 25-NB drugs like 25I-NBOMe by the same group of researchers.^[3]

See also

• Substituted mescaline analogue
• N-Benzylphenethylamine
• NBOMe-mescaline