2,4-Diamino-6-(hydroxymethyl)pteridine hydrochloride
[CAS# 73978-41-3]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 2,4-Diamino-6-(hydroxymethyl)pteridine hydrochloride
• Synonyms: (2,4-Diaminopteridin-6-yl)methanol hydrochloride
• Molecular Formula: C₇H₈N₆O.HCl
• Molecular Weight: 228.64
• CAS Registry Number: 73978-41-3
• EC Number: 700-274-8
• SMILES: C1=C(N=C2C(=NC(=NC2=N1)N)N)CO.Cl

Properties

• Melting point: 220 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

2,4-Diamino-6-(hydroxymethyl)pteridine hydrochloride is a pteridine derivative that has gained interest due to its unique structural features and potential applications in medicinal chemistry. Pteridines are heterocyclic compounds that play a key role in the biochemistry of living organisms, as they are involved in various metabolic pathways, including those related to the synthesis of cofactors such as folates and biopterins. The presence of amino and hydroxymethyl groups at specific positions on the pteridine ring makes 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride a versatile compound for developing therapeutic agents.

The discovery of 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride is linked to the ongoing search for inhibitors and modulators of enzymes involved in the biosynthesis of folic acid. This compound is structurally related to folate, a cofactor essential for DNA synthesis and repair. As a result, 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride and its derivatives have been studied for their potential to inhibit dihydrofolate reductase (DHFR), an enzyme critical in the folate metabolism pathway. By inhibiting DHFR, these compounds can interfere with cell growth and division, making them useful in cancer treatment.

The primary application of 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride is as a potential therapeutic agent in cancer and microbial infections. Due to its similarity to folate, it has been considered as a lead compound for the development of folate analogs that can block DHFR activity. DHFR inhibitors are important in cancer chemotherapy, as they can block the synthesis of nucleotides required for the growth of rapidly dividing cells. Furthermore, the compound’s potential use extends to treating infections caused by folate-dependent pathogens, such as certain bacteria and parasites.

In addition to its role in cancer and antimicrobial research, 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride has been explored for its activity in modulating the immune system. Some studies have suggested that pteridine derivatives may influence immune responses by interacting with enzymes involved in the metabolism of biopterins, which are essential for the production of nitric oxide. Nitric oxide is a signaling molecule that plays a crucial role in immune responses, vascular regulation, and neurotransmission. This makes 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride a promising compound for exploring novel treatments for immune-related diseases.

References

2012. The Pharmaceutical and Cosmetic Industries. Kanerva's Occupational Dermatology
DOI: 10.1007/978-3-642-02035-3_180