Alpha eucaine, also known as α-eucaine, is a synthetic organic compound known for its historical use as a local anesthetic. Its complex chemical architecture is characterized by a specific arrangement of carbon, hydrogen, nitrogen, and oxygen atoms, giving it a distinctive bicyclic structure.
Chemical Composition and Key Properties
The fundamental properties of alpha eucaine, including its atomic composition and molecular weight, are crucial for understanding its chemical identity.
| Property | Value |
|---|---|
| Formula | C19H27NO4 |
| Molar Mass | 333.428 g·mol⁻¹ |
Detailed Structural Description
The exact chemical structure of alpha eucaine can be precisely represented by its SMILES (Simplified Molecular Input Line Entry System) string, which provides a textual way to describe its molecular graph.
SMILES: O=C(OC1CC2C(C(C)(C)C1)N(C)C2)C3=CC=CC=C3
This SMILES notation reveals the following key structural features of alpha eucaine:
- Bicyclic Core: The molecule features a bicyclo[3.2.1]octane ring system, a bridged ring structure that is characteristic of compounds derived from the tropane alkaloid family. This rigid framework forms the backbone of the molecule.
- Ester Functional Group: A critical component is an ester linkage (
-COO-). This group connects a benzoic acid moiety to a hydroxyl group on the bicyclic core. Esters are often sites of metabolic breakdown in the body. - Aromatic Ring: A phenyl group (a benzene ring,
C6H5) is directly attached to the ester, contributing to the molecule's overall hydrophobicity and its ability to interact with biological receptors. - Tertiary Amine: Within the bicyclic system, there is a tertiary amine group (a nitrogen atom bonded to three carbon atoms), specifically methylated. This nitrogen is typically protonated in physiological environments, forming a charged species that is essential for its pharmacological action.
- Alkyl Substituents: The bicyclic ring also includes multiple methyl groups, including two gem-dimethyl groups (two methyl groups attached to the same carbon atom) and another single methyl group, influencing the molecule's three-dimensional shape and binding specificities.
Historical Significance
Alpha eucaine was among the first successful synthetic alternatives to cocaine, introduced in the late 19th century. Its development marked a significant step in the search for effective local anesthetics with a reduced potential for abuse compared to naturally derived compounds. Although largely superseded by newer, more potent, and safer anesthetics today, its structural design provided valuable insights for future drug development in the field of pain management.
