History, now and future of Adamantane

Adamantane is a colorless, crystalline chemical compound with a camphor-like odor. With a formula C10H16, it is a cycloalkane and also the simplest diamondoid. The molecules consist of four connected cyclohexane rings arranged in the "armchair" configuration. It is unique in that it is both rigid and virtually stress-free. 

Adamantane(CAS NO:281-23-2) is the most stable among all the isomers with formula C10H16, which include the somewhat similar twistane. The spatial arrangement of carbon atoms is the same in adamantane molecule and in the diamond crystal. This motivates the name adamantane, which is derived from the Greek adamantinos (relating to steel or diamond).

The discovery of adamantane in petroleum in 1933 launched a new chemistry field studying the synthesis and properties of polyhedral organic compounds. It derivatives have found practical application as drugs, polymeric materials and thermally stable lubricants.

The first attempt of laboratory synthesis was made by German chemist Hans Meerwein in 1924 using reaction of formaldehyde with diethyl malonate in the presence of piperidine. Instead of adamantane, Meerwein obtained 1,3,5,7-tetracarbomethoxybicyclo[3.3.1]nonane-2,6-dione. This compound was later named Meerwein's ester and used in the syntheses of adamantane and its derivatives.Later, another German chemist D. Bottger tried to obtain adamantane using Meerwein's ester as precursor. However, the product, tricyclo-[3.3.1.13,7] decane ring system, was again an adamantane derivative.

Adamantane itself enjoys few applications since it is merely an unfunctionalized hydrocarbon. It is used in some dry etching masks and polymer formulations. In solid-state NMR spectroscopy, adamantane is a common standard for chemical shift referencing. In dye lasers, adamantane may be used to extend the life of the gain medium; it cannot be photoionized under atmosphere because its absorption bands lie in the vacuum-ultraviolet region of the spectrum. Photoionization energies have been determined for this medicine as well as for several bigger diamondoids.

All medical applications known so far involve not pure adamantane, but its derivatives. The first adamantane derivative used as a drug was amantadine-first (1967) as an antiviral drug against various strains of flu and then to treat Parkinson's disease. Other drugs among adamantane derivatives include adapalene, amantadine, dopamantin, karmantadin, memantine, rimantadine, saxagliptin, tromantadine and vildagliptin. Polymers of adamantane have been patented as antiviral agents against HIV.

It was recently identified as a key structural subunit in several synthetic cannabinoid designer drugs, namely AB-001 and SDB-001

Some alkyl derivatives of adamantane have been used as a working fluid in hydraulic systems. Adamantane-based polymers might find application for coatings of touchscreens, and there are prospects for using adamantane and its homologues in nanotechnology. For example, the soft cage-like structure of adamantane solid allow incorporation of guest molecules, which can be released inside the human body upon breaking the matrix.

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