N-Bn-THAZ

N-Bn-THAZ is a selective agonist of the serotonin 5-HT_2A and 5-HT_2C receptors.^[1][2] It is a derivative of THAZ, which itself is a weak antagonist of the glycine and GABA_A receptors related to THIP (gaboxadol).^[2]

N-Bn-THAZ

Clinical data
Other names	N-Benzyl-THAZ
Drug class	Serotonin receptor agonist; Serotonin 5-HT2A and 5-HT2C receptor agonist
ATC code	None
Identifiers
IUPAC name 2-benzyl-5,6,7,8-tetrahydro-4H-[1,2]oxazolo[4,5-d]azepin-3-one
CAS Number	125115-66-4
PubChem CID	14515725
ChemSpider	14676439
ChEMBL	ChEMBL2331807
Chemical and physical data
Formula	C14H16N2O2
Molar mass	244.294 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CNCCC2=C1C(=O)N(O2)CC3=CC=CC=C3
InChI InChI=1S/C14H16N2O2/c17-14-12-6-8-15-9-7-13(12)18-16(14)10-11-4-2-1-3-5-11/h1-5,15H,6-10H2 Key:BWAFYEDXZXBSIK-UHFFFAOYSA-N

N-Bn-THAZ shows high affinity, activational potency, and efficacy at the serotonin 5-HT_2A and 5-HT_2C receptors.^[1][2] Its affinities (K_i) were 8,800 nM at the serotonin 5-HT_2A receptor and 2,300 nM at the serotonin 5-HT_2C receptor, while its activational activities (EC₅₀Tooltip half-maximal effective concentration [E_maxTooltip maximal efficacy]) were 550 to 2,400 nM (80–95%) at the serotonin 5-HT_2A receptor and 420 to 1,700 nM (90–92%) at the serotonin 5-HT_2C receptor.^[1][2] N-Bn-THAZ showed selectivity for these receptors over numerous other targets, notably including the serotonin 5-HT_2B receptor antitarget.^[2]

The drug has been found to produce pro-cognitive-like effects in rodents.^[2] These effects could be fully reversed by the selective serotonin 5-HT_2C receptor antagonist SB-242084.^[2] The researchers did not assess N-Bn-THAZ in terms of psychedelic-like effects, but as a serotonin 5-HT_2A receptor agonist, they noted that the drug could potentially produce hallucinogenic effects.^[2] Due to its lack of serotonin 5-HT_2B receptor activity, N-Bn-THAZ would not be expected to have the cardiovascular adverse effects of agonists of this receptor.^[2]

N-Bn-THAZ was developed by Povl Krogsgaard-Larsen and colleagues and was first described in the scientific literature by 2013.^[1][2] Structurally, N-Bn-THAZ is an isoxazole and is distinct from other serotonin 5-HT₂ receptor agonists, such as the tryptamines and phenethylamines.^[1][2] Other analogues of N-Bn-THAZ, such as O-Bn-THAZ, which is also active as a serotonin 5-HT₂ receptor agonist, have been synthesized and studied as well.^[1][2]

See also

• List of miscellaneous 5-HT_2A receptor agonists