5Br-INACA (5-bromo-1H-indazole-3-carboxamide, C₈H₆BrN₃O, MW 240.06) represents the simplest member of the 5-bromoindazole-3-carboxamide family — the fundamental scaffold shared by all 5-bromoindazole-based synthetic cannabinoids. Unlike its more complex analogues (MDMB-5Br-INACA, ADB-5Br-INACA, MMB-5Br-INACA), this compound lacks a lipophilic tail, serving as the synthetic precursor and analytical reference for the entire class.
Molecular Identity
| Parameter | Value |
|---|---|
| Common Name | 5Br-INACA |
| IUPAC Name | 5-Bromo-1H-indazole-3-carboxamide |
| Molecular Formula | C₈H₆BrN₃O |
| Molecular Weight | 240.06 g/mol |
| InChI Key | BLPIUDHMDGSMME-UHFFFAOYSA-N |
| SMILES | NC(=O)c1n[nH]c2c1cc(Br)cc2 |
| PubChem CID | 91809596 |
Significance as Core Scaffold
The carboxamide moiety (CONH₂) at position 3 replaces the carboxylic acid found in the precursor building block 5-bromo-1H-indazole-3-carboxylic acid (CAS 1077-94-7). This scaffold is invariant across all 5-bromoindazole cannabinoids — the tail groups (MMB, MDMB, ADB) attach via amide coupling at this position.
| Compound | Tail | MW |
|---|---|---|
| 5Br-INACA | None (NH₂) | 240.06 |
| MMB-5Br-INACA | Isopropyl | 354.20 |
| MDMB-5Br-INACA | tert-Butyl | 368.23 |
| ADB-5Br-INACA | tert-Butyl amide | 367.24 |
Analytical Data
¹H NMR (400 MHz, DMSO-d₆): δ 13.60 (br s, 1H, N-H), 8.10 (d, 1H, H-4), 7.85 (br s, 1H, CONH₂), 7.72 (br s, 1H, CONH₂), 7.62 (dd, 1H, H-6), 7.48 (d, 1H, H-7).
ESI-MS: [M+H]⁺ m/z 240.0/242.0 (Br isotope, 1:1) | HPLC: ≥ 97% purity
References
- Aipsin, Issue 38, Feb 2023: I-280; IV-23
- ChemSpider ID 44210086
- PubChem CID 91809596
Supply Information
Sun Pharma Chemical offers 5-bromo-1H-indazole-3-carboxylic acid (CAS 1077-94-7, $800/KG) — the direct synthetic precursor to 5Br-INACA and all 5-bromoindazole cannabinoid analogues. Available from stock.
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For laboratory research use only.