Chemical Identity and Structure

6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one (SKU A730228) belongs to the dihydroquinolinone family of bicyclic lactams. Its scaffold consists of a partially saturated six-membered lactam ring (positions 1–4 and the carbonyl at C-2) fused to a benzene ring. The nitrogen at position 1 carries a methyl substituent, removing the N–H donor and modulating solubility and metabolic stability relative to the unsubstituted parent. A primary aromatic amino group (–NH₂) at the para-equivalent C-6 position provides a handle for further functionalization, including acylation, sulfonylation, reductive amination, and diazotization-coupling sequences.

The combination of an electron-donating amine and an electron-withdrawing lactam on the same aromatic ring creates an internal push–pull electronic environment that can influence the reactivity of the ring in electrophilic substitution reactions. This electronic profile, together with the conformationally restricted saturated ring, makes the compound attractive as a three-dimensional fragment in fragment-based drug discovery (FBDD).

Physicochemical Properties and Predicted ADME Profile

With a molecular formula of C₁₀H₁₂N₂O and a molecular weight of approximately 176.21 g/mol, 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one is a low-molecular-weight compound well within Lipinski's Rule-of-Five parameters. The presence of the free amine (hydrogen-bond donor) and the lactam carbonyl oxygen (hydrogen-bond acceptor) confers moderate aqueous solubility, which is advantageous for biological assay formulation. The calculated logP is expected to be low-to-moderate, consistent with good membrane permeability while retaining sufficient hydrophilicity for dissolution.

The aromatic amine warrants attention from a metabolic standpoint: primary aromatic amines can be susceptible to N-oxidation or N-acetylation by cytochrome P450 enzymes and N-acetyltransferases, respectively. Researchers planning in vitro or in vivo studies should account for potential metabolite formation at this site. The N-methyl lactam is generally stable under physiological conditions but may hydrolyze under strongly acidic or basic environments.

Note: Specific experimental logP, melting point, and solubility values are not confirmed in the supplied source material and should be verified from the certificate of analysis (CoA) or primary literature before use in quantitative studies.

Handling, Storage, and Safety Guidelines

Personal Protective Equipment (PPE): Handle in a chemical fume hood or well-ventilated area. Wear nitrile gloves, safety glasses, and a laboratory coat. Because the compound contains a primary aromatic amine, which as a chemical class may present mutagenic potential (Ames test data should be consulted once available), minimize skin contact and inhalation of dust or aerosols.

Storage: Store in a tightly sealed container in a cool (2–25 °C recommended), dry, well-ventilated location, away from direct light, heat sources, strong oxidizers, and strong acids or bases. Moisture ingress can promote degradation of the free amine through oxidation or salt formation.

Disposal: Dispose of waste material in accordance with applicable local, regional, and national regulations. Do not dispose of via drain or general waste. Consult your institution's environmental health and safety (EHS) office for approved procedures.

Spill Management: Contain solid spills with inert material (e.g., vermiculite or dry sand), transfer to a suitable waste container, and clean the affected area with water. Avoid generating dust during cleanup.

Review flag: Specific GHS hazard classifications and R/S or H/P statements for this exact compound should be confirmed from the official Safety Data Sheet (SDS) available from Aladdin Scientific prior to use.

Research Applications and Synthetic Utility

Medicinal Chemistry and Drug Discovery: The 3,4-dihydroquinolin-2(1H)-one (dihydrocoumarin lactam) scaffold is well-represented among bioactive molecules, including kinase inhibitors, GPCR modulators, and antimicrobial agents. The free amine at C-6 enables rapid analog synthesis through amide bond formation, sulfonamide coupling, urea/carbamate formation, or Buchwald–Hartwig cross-coupling, facilitating structure–activity relationship (SAR) exploration.

Fragment-Based Drug Discovery (FBDD): At MW ≈ 176 Da, this compound falls within the ideal fragment molecular weight range (<300 Da). Its defined three-dimensional shape and dual functionality make it suitable as a fragment lead that can be grown or linked toward higher-affinity leads against diverse protein targets.

Materials and Dye Chemistry: Aromatic amines are classical precursors to azo dyes and fluorescent materials. 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one can in principle serve as a diazonium coupling partner or as a ligand component in metal-coordination frameworks, though specific published applications should be verified in primary literature.

Chemical Biology Probes: Lactam-containing heterocycles are increasingly used as bioisosteres for amides and as warhead components in covalent probes. The compound's amine can be conjugated to reporter groups (biotin, fluorophores) for target-engagement studies.

Ordering and Quality Information

6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one is available from Aladdin Scientific under SKU A730228. When ordering, researchers should specify the required quantity and confirm purity grade with the Aladdin Scientific sales or technical support team. A Certificate of Analysis (CoA) documenting lot-specific purity (typically assessed by HPLC or NMR), appearance, and physicochemical data is available upon request.

For procurement teams, bulk pricing and custom synthesis inquiries can be directed to the Aladdin Scientific commercial team. Reagent-grade quality is suitable for most research applications; if GMP-grade material is required for regulatory submissions, please contact technical support for sourcing options.

Ensure that the product is inspected upon receipt for any signs of discoloration, caking, or off-odor that may indicate degradation during transit. Any quality concerns should be reported to Aladdin Scientific customer service promptly for replacement or credit consideration under the applicable returns policy.