(1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride
[CAS# 601515-79-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: (1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride
• Molecular Formula: C₅H₁₀ClNO
• Molecular Weight: 135.59
• CAS Registry Number: 601515-79-1
• EC Number: 844-441-4
• SMILES: C1[C@@H]2CN[C@H]1CO2.Cl

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
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

(1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride is a hydrochloride salt form of a structurally rigid bicyclic compound containing both nitrogen and oxygen heteroatoms in a fused ring system. The compound is a derivative of the azabicycloheptane scaffold, commonly known as tropane or related to oxazabicyclic structures, with stereochemistry defined at the 1 and 4 positions, which contributes to its conformational stability and potential biological activity.

This compound was developed in the context of research on neurotransmitter reuptake inhibitors and receptor ligands. The bicyclic framework of (1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptane shares structural features with known pharmacophores in neuromodulatory agents, particularly those targeting monoamine systems such as the dopamine, norepinephrine, and serotonin transporters. The hydrochloride form is often used to improve the solubility and stability of the compound for experimental and pharmaceutical applications.

The initial identification and synthesis of this molecule were part of medicinal chemistry efforts to create analogs of biologically active alkaloids and synthetic neurotransmitter inhibitors. The presence of both nitrogen and oxygen atoms in a bridged bicyclic system makes the compound a valuable scaffold for probing central nervous system (CNS) targets. The structural rigidity imposed by the bicyclic ring system reduces conformational flexibility, which can enhance the binding affinity and selectivity of ligands for their biological targets.

Applications of (1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride are primarily found in drug discovery and receptor binding studies. The compound has been investigated as a building block in the synthesis of ligands for CNS receptors, including those involved in mood regulation and cognitive function. In particular, the compound's ability to serve as a conformationally restricted analog of neurotransmitter amines makes it useful for the design of selective ligands that can differentiate between closely related receptor subtypes or transporter proteins.

Additionally, this compound is utilized in structure–activity relationship (SAR) studies, where modifications to the core structure help elucidate the molecular determinants of receptor binding and activity. Its bicyclic structure serves as a rigid template that allows systematic substitution at specific positions to modulate pharmacological properties such as potency, selectivity, and metabolic stability.

Beyond its use in neuropharmacology, the compound has also been explored in the context of chemical biology and synthetic organic chemistry. The functional groups present in (1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride offer opportunities for further derivatization, making it a versatile intermediate in the preparation of complex molecular architectures. Its ability to maintain stereochemical integrity during chemical transformations enhances its utility in asymmetric synthesis and chiral drug development.

References

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