(6R)-1,6-Dihydro-N2,N2,6-trimethyl-1,3,5-triazine-2,4-diamine hydrochloride
[CAS# 775351-61-6]

Identification

• Classification: API >> Other chemicals
• Name: (6R)-1,6-Dihydro-N2,N2,6-trimethyl-1,3,5-triazine-2,4-diamine hydrochloride
• Synonyms: (4R)-6-N,6-N,4-trimethyl-1,4-dihydro-1,3,5-triazine-2,6-diamine;hydrochloride
• Molecular Formula: C₆H₁₃N₅.x(HCl)
• CAS Registry Number: 775351-61-6
• SMILES: C[C@@H]1N=C(NC(=N1)N(C)C)N.Cl

Properties

• Solubility: H2O: 2 mg/mL (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

(6R)-1,6-Dihydro-N₂,N₂,6-trimethyl-1,3,5-triazine-2,4-diamine hydrochloride is a chemical compound belonging to the class of triazine derivatives. The molecule features a 1,3,5-triazine ring, a six-membered heterocyclic system containing three nitrogen atoms at alternating positions. The designation (6R) specifies the absolute configuration at the chiral center located at the sixth position of the ring, indicating the spatial arrangement of the substituents in the molecule.

This compound is characterized by methyl substitutions at the N₂ and 6 positions, alongside diamine functionalities at the 2 and 4 positions of the triazine ring. The hydrochloride form indicates that the compound exists as a salt, with protonation occurring typically at the amino groups, which enhances its solubility and stability under various conditions.

The discovery and synthesis of such triazine derivatives stem from the extensive research into heterocyclic compounds due to their broad biological and chemical significance. Triazine rings are well-known scaffolds in medicinal chemistry, agrochemicals, and materials science because they offer versatile chemical reactivity and the ability to engage in hydrogen bonding and other intermolecular interactions.

Applications of (6R)-1,6-dihydro-N₂,N₂,6-trimethyl-1,3,5-triazine-2,4-diamine hydrochloride primarily relate to its potential use as a building block or intermediate in pharmaceutical and chemical synthesis. The structural features of this compound allow it to participate in reactions that yield more complex molecules, including drugs or functional materials.

In medicinal chemistry, triazine derivatives have been studied for their antiviral, antibacterial, and anticancer properties. While specific biological activities of this exact compound are limited in well-established literature, its close structural relatives have shown bioactivity, making this compound of interest for further research and development.

Additionally, the hydrochloride salt form facilitates its use in aqueous systems and biological assays, enabling studies of its interactions and effects in physiological conditions.

In summary, (6R)-1,6-dihydro-N₂,N₂,6-trimethyl-1,3,5-triazine-2,4-diamine hydrochloride is a triazine-based compound characterized by specific methyl and amino substitutions and chiral configuration. It serves as a valuable intermediate in synthetic chemistry, with potential applications in pharmaceutical development and materials science due to the versatile chemistry of the triazine core.

References

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DOI: 10.1007/s40262-020-00948-1

2021. Imeglimin Hydrochloride: First Approval. Drugs, 81(14).
DOI: 10.1007/s40265-021-01589-9

2022. Pharmacokinetics of Imeglimin in Caucasian and Japanese Healthy Subjects. Clinical Drug Investigation, 42(8).
DOI: 10.1007/s40261-022-01181-3