ADB-5′Br-EZO-CA (N-[(2S)-1-amino-3,3-dimethyl-1-oxobutan-2-yl]-5-bromo-1H-benzimidazole-2-carboxamide, C₁₄H₁₇BrN₄O₂, MW 353.21) represents a structurally distinct cannabinoid chemotype featuring a benzimidazole core rather than the indazole scaffold common to the INACA series.
Molecular Identity
| Parameter | Value |
|---|---|
| Common Name | ADB-5′Br-EZO-CA |
| IUPAC Name | N-[(2S)-1-Amino-3,3-dimethyl-1-oxobutan-2-yl]-5-bromo-1H-benzimidazole-2-carboxamide |
| Molecular Formula | C₁₄H₁₇BrN₄O₂ |
| Molecular Weight | 353.21 g/mol |
| InChI Key | VFBTZKNPNPCLDM-SNVBAGLBSA-N |
| SMILES | NC(=O)[C@H](C(C)(C)C)NC(=O)c1nc2c([nH]1)ccc(c2)Br |
Benzimidazole vs Indazole Core
The “EZO” designation indicates a benzimidazole-2-carboxamide scaffold — distinct from the indazole-3-carboxamide (INACA) series. Benzimidazole places two nitrogen atoms in a 1,3-arrangement (imidazole), whereas indazole has adjacent nitrogens (pyrazole). This alters hydrogen-bonding capability and electronic distribution across the core.
Analytical Data
¹H NMR (400 MHz, DMSO-d₆): δ 13.20 (br s, 1H, N-H), 8.40 (d, 1H, amide N-H), 7.85 (d, 1H, H-4), 7.55 (dd, 1H, H-6), 7.40 (d, 1H, H-7), 7.25 (br s, 1H, CONH₂), 7.05 (br s, 1H, CONH₂), 4.48 (d, 1H, CH-CONH₂), 1.02 (s, 9H, C(CH₃)₃).
ESI-MS: [M+H]⁺ m/z 353.1/355.1 (Br isotope, 1:1) | HPLC: ≥ 97% purity
Reference
- Aipsin, Issue 40, Apr 2023: I-316 — ADB-5′Br-EZO-CA
Supply Information
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