adamantane

Adamantane is the simplest member of the adamantane family of hydrocarbons. It is a saturated hydrocarbon with the molecular formula C10H16 and the IUPAC name tricyclo[3.3.1.1^3,7]decane. The molecule features a rigid, cage-like framework with high symmetry, described by a tricyclic, fully saturated structure that forms a three-dimensional, diamond-like lattice at a molecular scale.

Structure and properties

Adamantane consists of three fused cyclohexane rings arranged to create a tetrahedral, highly symmetric cage. The framework is composed entirely of carbon–carbon single bonds, giving it exceptional stability compared with many other hydrocarbons. Its rigid geometry confers notable thermal stability and chemical inertness relative to many other saturated hydrocarbons. It is a solid at room temperature, insoluble in water, and soluble in many organic solvents.

Reactivity and derivatives

As a saturated hydrocarbon, adamantane itself is relatively unreactive. Functionalization is possible at the cage’s bridgehead or 1-position to yield 1-substituted adamantanes, among other derivatives. The adamantane scaffold is prized in medicinal chemistry and materials science for its rigid, bulky, hydrophobic core, which can improve the pharmacokinetic and binding properties of molecules.

Applications and notable compounds

Adamantane derivatives are widely used as building blocks in drug design. Notable examples include amantadine, a drug with antiviral and anti-Parkinsonian indications, and memantine, used in the management of Alzheimer's disease. The adamantane skeleton remains a valuable motif in supramolecular chemistry and pharmaceutical research.

Name and origin

The name adamantane derives from adamant, a historical term for diamond-like hardness, reflecting the compound’s rigid, cage-like structure.