8-Aminoisoquinoline
[CAS# 23687-27-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: 8-Aminoisoquinoline
• Synonyms: isoquinolin-8-amine
• Molecular Formula: C₉H₈N₂
• Molecular Weight: 144.17
• CAS Registry Number: 23687-27-6
• EC Number: 691-616-4
• SMILES: C1=CC2=C(C=NC=C2)C(=C1)N

Properties

• Melting point: 155-157 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

8-Aminoisoquinoline is a compound of significant interest in organic chemistry and medicinal research due to its unique structure and diverse range of applications. As a member of the isoquinoline family, 8-aminoisoquinoline features an amino group attached to the 8-position of the isoquinoline ring, which is a bicyclic heterocyclic system comprising a benzene ring fused to a pyridine ring.

The discovery of 8-aminoisoquinoline dates back to early research into isoquinoline derivatives, which have been known for their varied biological activities. The amino group at the 8-position introduces additional reactivity and potential for forming new derivatives with modified properties. The synthesis of 8-aminoisoquinoline typically involves the nitration of isoquinoline followed by reduction and amination steps, which allow for the selective introduction of the amino group.

The applications of 8-aminoisoquinoline span several fields, with a notable emphasis on medicinal chemistry. One of its primary applications is as a scaffold in the development of pharmaceuticals. The compound's ability to form hydrogen bonds and interact with biological targets makes it a valuable building block for designing new drugs. For instance, 8-aminoisoquinoline derivatives have been investigated for their potential as enzyme inhibitors and receptor modulators.

In particular, 8-aminoisoquinoline and its derivatives have shown promise in the development of antimalarial agents. Researchers have explored these compounds for their ability to inhibit the growth of Plasmodium species, the parasites responsible for malaria. The structural modifications made to the 8-aminoisoquinoline core can enhance its potency and selectivity against these parasites, contributing to the search for effective treatments for malaria.

Additionally, 8-aminoisoquinoline has been studied for its potential in treating cancer. The compound's interaction with cellular targets involved in cancer progression, such as kinases and transcription factors, makes it a candidate for anticancer drug development. The development of novel derivatives with improved bioactivity and reduced toxicity is an ongoing area of research.

In the field of material science, 8-aminoisoquinoline has also found applications. Its ability to form coordination complexes with metal ions makes it useful in the synthesis of new materials with specific optical and electronic properties. These materials can be utilized in sensors, catalysts, and other advanced technologies.

The synthesis of 8-aminoisoquinoline typically involves the preparation of the isoquinoline core followed by selective nitration, reduction, and amination. This process requires careful control of reaction conditions to achieve high yields and purity of the final product.

In summary, 8-aminoisoquinoline is a versatile compound with significant potential in medicinal chemistry and material science. Its unique structural features enable a range of applications, from drug development to advanced materials. Continued research into its derivatives and their biological activities promises to uncover new therapeutic possibilities and applications.

References

2007. Application of fragment screening by X-ray crystallography to beta-secretase. Journal of Medicinal Chemistry, 50(5), 1124–1132.
DOI: 10.1021/jm0611962

2019. Rhodium-catalyzed C–H activation/annulation of amidines with 4-diazoisochroman-3-imines toward isochromeno[3,4-c]isoquinolines. Organic & Biomolecular Chemistry, 17(36), 8424–8428.
DOI: 10.1039/c9ob01576a

1956. Studies of the amino-isoquinolines, -cinnolines, and -quinazolines. Journal of the Chemical Society, 4206–4212.