MDMB-5Br-INACA (methyl (2S)-2-[(5-bromo-1H-indazole-3-carbonyl)amino]-3,3-dimethylbutanoate) is a synthetic cannabinoid featuring a 5-bromo-substituted 1H-indazole-3-carboxamide core coupled with an MDMB tail. The bromine at the 5-position introduces distinct electronic and steric effects that modulate cannabinoid receptor affinity compared to the parent MDMB-INACA.
Molecular Identity
| Parameter | Value |
|---|---|
| Common Name | MDMB-5Br-INACA |
| IUPAC Name | Methyl (2S)-2-[(5-bromo-1H-indazole-3-carbonyl)amino]-3,3-dimethylbutanoate |
| Molecular Formula | C₁₅H₁₈BrN₃O₃ |
| Molecular Weight | 368.23 g/mol |
| InChI Key | QGEVEXPJOKFMAN-GFCCVEGCSA-N |
| SMILES | COC(=O)[C@H](C(C)(C)C)NC(=O)c1n[nH]c2c1cc(Br)cc2 |
| PubChem CID | 165362085 |
Halogen Substitution Effects
The 5-bromo substitution (MW 368.23, logP ~3.3) compared to parent MDMB-INACA (MW 289.33, logP ~2.8) increases lipophilicity by ~0.5 log units. The bromine atom provides a distinctive 1:1 isotopic doublet in mass spectrometry (⁷⁹Br:⁸¹Br) and serves as a key structural feature for forensic identification. This 5-bromo pattern is a common SAR motif in indazole-3-carboxamide cannabinoids, often correlated with enhanced CB₁ receptor affinity.
Synthetic Route
The synthesis utilizes 5-bromo-1H-indazole-3-carboxylic acid (CAS 1077-94-7) as the key building block, activated with CDI or HATU and coupled with (S)-methyl 2-amino-3,3-dimethylbutanoate hydrochloride under basic conditions (DIPEA, DCM). Typical yields range from 70-85% after purification. This 5-bromo carboxylic acid building block is commercially available and versatile for a broad range of 5-substituted indazole-3-carboxamides.
Analytical Data
¹H NMR (400 MHz, DMSO-d₆): δ 13.80 (br s, 1H, N-H), 8.55 (d, 1H, amide N-H), 8.15 (d, 1H, H-4), 7.68 (dd, 1H, H-6), 7.52 (d, 1H, H-7), 4.65 (d, 1H, CH-CO₂Me), 3.72 (s, 3H, OCH₃), 1.08 (s, 9H, C(CH₃)₃).
ESI-MS: [M+H]⁺ m/z 368.1/370.1 (Br isotope pattern, 1:1) | HPLC: ≥ 97% purity
References
- Aipsin, Issue 33, Sep 2022: III-125
- Aipsin, Issue 27, Mar 2022: I-199
- Aipsin, Issue 47, Nov 2023: VII-268
- ChemSpider 114952001
- PubChem CID 165362085
- CFSRE Chemistry Report, May 2022
Supply Information
Sun Pharma Chemical offers high-purity 5-bromo-1H-indazole-3-carboxylic acid (CAS 1077-94-7) and related indazole building blocks for pharmaceutical research.
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