MDMB-INACA (methyl N-(1H-indazole-3-carbonyl)-3-methylvalinate) is a synthetic cannabinoid belonging to the indazole-3-carboxamide class. This compound features a 1H-indazole-3-carboxylic acid core coupled with a methyl 3,3-dimethylbutanoate (MDMB) tail via an amide linkage. Structurally analogous to the ADB-5Br-INACA series but lacking halogen substitution, MDMB-INACA represents a foundational scaffold within the indazole-3-carboxamide cannabinoid family.
Molecular Identity
| Parameter | Value |
|---|---|
| Common Name | MDMB-INACA |
| IUPAC Name | Methyl N-(1H-indazole-3-carbonyl)-3-methylvalinate |
| CAS Number | 2709672-58-0 |
| Molecular Formula | C₁₅H₁₉N₃O₃ |
| Molecular Weight | 289.33 g/mol |
| InChI Key | QEXPVGIGOZJEOO-UHFFFAOYSA-N |
| SMILES | COC(=O)C(C(C)(C)C)NC(=O)c1n[nH]c2c1cccc2 |
| PubChem CID | 165361543 |
Structural Overview
The molecular architecture of MDMB-INACA consists of three key structural components:
- 1H-Indazole Core — A fused bicyclic heteroaromatic system comprising a benzene ring fused to a pyrazole ring. This core provides the primary π-stacking interaction surface for cannabinoid receptor (CB₁/CB₂) binding.
- Carboxamide Linker — The 3-position of the indazole ring bears a carboxamide (-CONH-) functional group, which serves as the critical hydrogen-bond donor/acceptor motif responsible for receptor recognition.
- MDMB Ester Tail — The N-(methyl 3,3-dimethylbutanoate) substituent features a bulky tert-butyl group (3,3-dimethyl) adjacent to the chiral α-carbon center. The methyl ester terminus contributes to the overall lipophilicity required for blood-brain barrier penetration.
Physicochemical Properties
- logP (calculated): ~2.8 — Optimal lipophilicity for CNS penetration
- Hydrogen Bond Donors: 2 (indazole N-H, amide N-H)
- Hydrogen Bond Acceptors: 4 (amide C=O, ester C=O, indazole N, ester O)
- Rotatable Bonds: 5 — Conformational flexibility for receptor adaptation
- Polar Surface Area (PSA): ~84 Ų — Within the acceptable range for CNS-active compounds
Receptor Pharmacology
MDMB-INACA acts as a potent agonist at both cannabinoid receptor subtypes. The indazole-3-carboxamide scaffold, when paired with the MDMB tail, exhibits enhanced CB₁ selectivity compared to its indole-based analogs (e.g., MDMB-ICA). The absence of a 5-halogen substituent (cf. ADB-5Br-INACA or MDMB-5Br-INACA) may modulate the binding kinetics and functional selectivity profile.
Synthetic Considerations
The general synthetic route to MDMB-INACA involves activation of 1H-indazole-3-carboxylic acid (CAS 4498-67-3) via CDI or thionyl chloride, followed by amide coupling with methyl 3-amino-3,3-dimethylbutanoate hydrochloride under basic conditions (Et₃N or DIPEA in anhydrous DCM or THF). Typical yields range from 65-85% after purification by column chromatography.
Analytical Data
¹H NMR (400 MHz, CDCl₃): δ 10.85 (br s, 1H, indazole N-H), 8.25 (d, J = 8.0 Hz, 1H, Ar-H), 7.62 (d, J = 8.2 Hz, 1H, Ar-H), 7.45 (t, J = 7.6 Hz, 1H, Ar-H), 7.28 (t, J = 7.6 Hz, 1H, Ar-H), 6.95 (br d, 1H, amide N-H), 4.68 (d, J = 9.0 Hz, 1H, CH-CO₂Me), 3.78 (s, 3H, OCH₃), 1.12 (s, 9H, C(CH₃)₃).
ESI-MS: [M+H]⁺ m/z 290.2, [M+Na]⁺ m/z 312.1
HPLC Purity: ≥ 97% (area normalization, UV 254 nm, C18 reverse phase, MeCN/H₂O gradient)
References
- Aipsin, Issue 17, May 2021: V-15
- Aipsin, Issue 39, Mar 2023: XII-64; XII-65
- Aipsin, Issue 41, May 2023: XII-73
- PubChem CID 165361543
- Project Response — MDMB-INACA, Report 2074-19
Supply Information
Sun Pharma Chemical offers high-purity MDMB-INACA (CAS 2709672-58-0) for research purposes.
For inquiries, quotations, or technical documentation, please contact us:
Telegram: @vv998800
Email: sunlele8888@gmail.com
Signal: aaaa.521
WhatsApp: +447942842649
All products are intended for laboratory research use only. Not for human consumption.