NBOMe-escaline

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;

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]

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]

References

^ ^a ^b ^c ^d ^e Pertz HH, Rheineck A, Elz S (1999). "N-Benzylated derivatives of the hallucinogenic drugs mescaline and escaline as partial agonists at rat vascular 5-HT2A receptors". Naunyn-Schmiedeberg's Archives of Pharmacology. 359 (Suppl 3): R29.
^ ^a ^b ^c ^d Ratzeburg K, Heim R, Mahboobi S, Henatsch J, Pertz HH, Elz S (March 2003). "Abstracts (pages 29-35): Potent Partial 5-HT_2A-Receptor Agonism of Phenylethanamines Related to Mescaline in the Rat Tail Artery Model". Naunyn-Schmiedeberg's Archives of Pharmacology. 367 (S1): R29–R35 (R31–R31). doi:10.1007/s00210-003-0720-9. ISSN 0028-1298. Retrieved 31 May 2025.
^ Heim R, Pertz HH, Elz S (1999). "Preparation and in vitro pharmacology of novel secondary amine-type 5-HT2A receptor agonists: from submillimolar to subnanomolar activity". Arch. Pharm. Pharm. Med. Chem. 332 (Suppl. 1): 34.

External links

NBOMe-escaline - Isomer Design

This hallucinogen-related article is a stub. You can help Wikipedia by expanding it.

[Pertz_1999-1] Pertz HH, Rheineck A, Elz S (1999). "N-Benzylated derivatives of the hallucinogenic drugs mescaline and escaline as partial agonists at rat vascular 5-HT2A receptors". Naunyn-Schmiedeberg's Archives of Pharmacology. 359 (Suppl 3): R29.

[Ratzeburg_2003-2] Ratzeburg K, Heim R, Mahboobi S, Henatsch J, Pertz HH, Elz S (March 2003). "Abstracts (pages 29-35): Potent Partial 5-HT_2A-Receptor Agonism of Phenylethanamines Related to Mescaline in the Rat Tail Artery Model". Naunyn-Schmiedeberg's Archives of Pharmacology. 367 (S1): R29–R35 (R31–R31). doi:10.1007/s00210-003-0720-9. ISSN 0028-1298. Retrieved 31 May 2025.

[Heim_1999-3] Heim R, Pertz HH, Elz S (1999). "Preparation and in vitro pharmacology of novel secondary amine-type 5-HT2A receptor agonists: from submillimolar to subnanomolar activity". Arch. Pharm. Pharm. Med. Chem. 332 (Suppl. 1): 34.

[1]

[2]

[3]

See also

References

External links