ZC-B

ZC-B
Identifiers
	IUPAC name 3-(4-bromo-2,5-dimethoxyphenyl)azetidine;
CAS Number	2641630-65-9;
PubChem CID	156337249;
UNII	9EP4MV3URL;
Chemical and physical data
Formula	C11H14BrNO2
Molar mass	272.142 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC(=C(C=C1C2CNC2)OC)Br;
	InChI InChI=1S/C11H14BrNO2/c1-14-10-4-9(12)11(15-2)3-8(10)7-5-13-6-7/h3-4,7,13H,5-6H2,1-2H3; Key:YFCASESLVDHSAW-UHFFFAOYSA-N;

ZC-B (3-(4-bromo-2,5-dimethoxyphenyl)azetidine) is a phenethylamine derivative which acts as a serotonin receptor agonist selective for the 5-HT₂ subtypes, with an EC₅₀ of 1.6nM at 5-HT_2A, vs 5.8nM at 5-HT_2C. It is structurally related to the psychedelic phenethylamines 2C-B and DOB, but with the amine side chain conformationally restricted as an azetidine ring.^[1]^[2]^[3]

References

^ US 2021/0137908, Kristensen JL, Jensen AA, Märcher-Rørsted E, "5-HT2A Agonists for Use in Treatment of Depression.", published 13 May 2021, assigned to Lophora ApS.
^ WO 2022/221774, Johnson G, Nichols DE, Maillet EL, "Aryl-ring-substituted 3-phenylazetidines and their use in methods for treating 5-HT2 responsive conditions", published 2022-10-20, assigned to leusis Therapeutics US Inc.
^ Sabnis RW (September 2025). "Novel Compounds as 5‑HT2A Agonists for Treating Depression". ACS Medicinal Chemistry Letters. 16 (9): 1709–1710. doi:10.1021/acsmedchemlett.5c00461. PMID 40959260.

[1] US 2021/0137908, Kristensen JL, Jensen AA, Märcher-Rørsted E, "5-HT2A Agonists for Use in Treatment of Depression.", published 13 May 2021, assigned to Lophora ApS.

[2] WO 2022/221774, Johnson G, Nichols DE, Maillet EL, "Aryl-ring-substituted 3-phenylazetidines and their use in methods for treating 5-HT2 responsive conditions", published 2022-10-20, assigned to leusis Therapeutics US Inc.

[Sabnis_2025-3] Sabnis RW (September 2025). "Novel Compounds as 5‑HT2A Agonists for Treating Depression". ACS Medicinal Chemistry Letters. 16 (9): 1709–1710. doi:10.1021/acsmedchemlett.5c00461. PMID 40959260.

[1]

[2]

[3]

See also

References