3-Amino-3-azabicyclo[3.3.0]octane hydrochloride
[CAS# 58108-05-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: 3-Amino-3-azabicyclo[3.3.0]octane hydrochloride
• Molecular Formula: C₇H₁₄N₂.HCl
• Molecular Weight: 162.66
• CAS Registry Number: 58108-05-7
• EC Number: 261-131-9
• SMILES: C1CC2CN(CC2C1)N.Cl

Properties

• Melting point: 170-174 °C (Expl.)

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
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	2	H335

Discovery and Applications

3-Amino-3-azabicyclo[3.3.0]octane hydrochloride is a bicyclic amine compound known for its unique structure and wide application in medicinal chemistry, especially as a building block in the synthesis of pharmaceutical agents. Its discovery stems from research into rigid amine structures, which offer valuable three-dimensional frameworks for drug development, improving both specificity and binding efficiency to target biomolecules. The bicyclic framework of 3-amino-3-azabicyclo[3.3.0]octane creates a constrained structure that limits conformational flexibility, often enhancing receptor selectivity and interaction.

Primarily, this compound is utilized in the synthesis of ligands and inhibitors in central nervous system (CNS) drug development. Its unique structure allows it to serve as a versatile scaffold for designing drugs targeting various neurological pathways, including dopamine and serotonin receptors. These pathways are central to numerous CNS conditions, such as depression, schizophrenia, and Parkinson’s disease. The constrained amine group within this compound makes it particularly effective in binding to receptors involved in neurotransmission, providing a starting point for developing selective receptor modulators with minimized side effects.

In addition to CNS applications, 3-amino-3-azabicyclo[3.3.0]octane hydrochloride has also found utility in the study of enzyme inhibitors. The rigidity and stability of the bicyclic scaffold are advantageous in developing compounds with prolonged binding activity, making it valuable for time-dependent enzyme inhibition. Recent research has also expanded its applications to oncology, where its derivatives show promise in cancer research as potential inhibitors of specific cancer cell growth receptors. This compound’s versatility continues to make it an area of interest in both medicinal and synthetic chemistry for producing biologically active molecules with enhanced selectivity and efficacy.

References

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