MMDPPA CAS 858215-05-1 is comprised of a 1,3-benzodioxole (methylenedioxyphenyl) moiety connected via a three-carbon chain to a primary amide (-CONH₂) group. The presence of a methyl substituent at the alpha-carbon (C-2) of the propanamide chain creates a chiral center, resulting in (R)- and (S)-enantiomers. The benzodioxole ring is a common pharmacophore known to influence metabolic stability and receptor binding.
Nombre :
MMDPPAN.º CAS :
858215-05-1MF :
C₁₁H₁₃NO₃MW :
207.23Pureza :
≥97%Apariencia :
a white to off-white crystalline or powdery solidCondición de almacenamiento :
Store in a cool, dry place.Chemical Properties
IUPAC Name: 3-(1,3-Benzodioxol-5-yl)-2-methylpropanamide
Synonyms: AG-205 (common research code); 2-Methyl-3-(3,4-methylenedioxyphenyl)propanamide; 3-(Benzo[d][1,3]dioxol-5-yl)-2-methylpropanamide
CAS Registry Number: 858215-05-1
Molecular Formula: C₁₁H₁₃NO₃
Molecular Weight: 207.23 g/mol
Appearance: Typically a white to off-white crystalline or powdery solid.
Melting Point: Data is limited. Estimated range: 120-140 °C (depending on purity and crystal form).
Solubility: Exhibits moderate lipophilicity. Expected to be:
Soluble in common organic solvents (DMSO, ethanol, methanol, acetone).
Sparingly soluble to slightly soluble in water due to the amide group.
Stability: Stable under standard laboratory conditions. The amide bond is generally stable, but the compound should be protected from prolonged exposure to strong acids/bases, light, and moisture. Store in a cool, dry place.
Biological Activities
This compound is best characterized as a research chemical or a pharmaceutical intermediate. Its primary biological interest is structural, related to its role as a precursor or analog in medicinal chemistry.
Primary Research Context: It is primarily reported in scientific and patent literature as a key intermediate in the synthesis of compounds targeting the endocannabinoid system, specifically for the development of cannabinoid receptor 1 (CB1) inverse agonists/antagonists.
Mechanism & Analogy: The structure incorporates elements (lipophilic aromatic system, amide linker) found in first-generation CB1 antagonists like Rimonabant. While the amide itself may not be a potent drug, it serves as a crucial building block for constructing more complex molecules designed to modulate appetite, metabolism, and energy balance.
Potential Activity: As a standalone molecule, specific pharmacological data (IC₅₀, Ki values) is scarce. Its activity would be expected to be significantly lower than that of the final drug candidates it helps to build. Any activity would likely be related to weak interaction with peripheral or central receptors of the endocannabinoid system.
Biosynthesis/Synthesis
This is a synthetic compound with no known natural biosynthetic pathway. A typical laboratory synthesis route involves:
1.Starting Material: 3,4-Methylenedioxyphenylacetone (piperonylacetone) or a similar benzodioxole-containing precursor.
2.Chain Elongation & Functionalization: The ketone is subjected to a reaction like the Henry reaction (nitroaldol) or homologation to introduce the additional carbon and a nitrile group.
3.Stereoselective Reduction/Modification: For enantiomerically pure material, an asymmetric reduction or resolution step may be employed to control the stereochemistry at the chiral 2-methyl center.
4.Amide Formation: The final step involves the hydrolysis of a nitrile intermediate or the direct amidation of the corresponding acid (3-(1,3-benzodioxol-5-yl)-2-methylpropanoic acid) to yield the target amide.
Applications
FAQs
Q1: What is the main purpose of this compound?
A: It is predominantly a synthetic intermediate used in academic and industrial research labs to create more complex drug candidates, particularly those related to cannabinoid receptor research.
Q2: Is it a controlled substance or banned?
A: As of now, 3-(1,3-benzodioxol-5-yl)-2-methylpropanamide itself is not specifically listed in major international drug control schedules (like the UN 1961/1971 Conventions or the US CSA). However, due to its structural relationship to regulated compounds, its sale and use may be monitored. It is sold for research purposes only and is not intended for human or veterinary use.
Q3: Where can I purchase it, and what purity is available?
A: It is available from specialized suppliers of fine chemicals and research compounds, such as Thermo Fisher Scientific etc. It is typically offered in milligram to gram quantities with purities ranging from 95% to 98%+ (by HPLC). Chiral versions (enantiomerically pure) may also be available at a higher cost.
Q4: What are the safety and handling precautions?
A: While a full toxicological profile may not be established, it should be treated as a potential health hazard.
Personal Protective Equipment (PPE): Always wear appropriate PPE: lab coat, safety glasses, and nitrile gloves.
Handling: Use in a well-ventilated area or chemical fume hood. Avoid creating dust or aerosols.
Storage: Store in a cool, dry, and well-ventilated place, away from incompatible materials. Keep the container tightly closed.
Always consult the Safety Data Sheet (SDS) provided by the supplier before handling.
Q5: Does it have any direct therapeutic or supplement use?
A: No. This compound is strictly a research chemical. It has not been approved as a drug or dietary supplement by any regulatory agency (FDA, EMA, etc.). Its use is confined to laboratory research.
Q6: What are its main spectroscopic identifiers for analysis?
A: Key identifiers include:
HPLC/LC-MS: Retention time and [M+H]⁺/m/z208.1.
¹H NMR: The distinctive singlet for the methylenedioxy protons (~5.95 ppm) and the amide proton signals.
IR Spectroscopy: Strong stretches for the amide carbonyl (C=O, ~1680 cm⁻¹) and N-H bonds.
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