|Molar mass||136.238 g/mol|
|Appearance||white to off-white powder|
|Density and phase||1.07 g/cm3|
|Solubility in water||insoluble in water|
|Solubility in other solvents||Soluble in hydrocarbons|
|Crystal structure||cubic, space group Fm3m|
|Dipole moment||0 D|
|Related compounds|| Memantine, NH2
| Except where noted otherwise, data are given for|
materials in their standard state (at 25 °C, 100 kPa)
Disclaimer and references
Adamantane is a diamondoid that was synthesized in 1941. Diamondoids are carbon cage molecules, which are the smallest unit cage structure of the diamond crystal lattice. It is a hydrocargon composed of ten carbon atoms and sixteen hydrogen atoms. Its derivatives are used in drugs, especially antivirals for ailments such as influenza and Parkinson's disease. It can also be potentially harmful to the body if it comes into contact with the skin, eyes, or is consumed.
Adamantane is an organic substance that can be toxic to aquatic life and can have harmful or irritating effects on humans if excessive exposure occurs. This substance and all of its derivatives are very highly reactive. It is known to be able to block ion channels, preventing the multiplication of various viruses. This is why adamantane's derivatives are so useful in the medical field.
Adamantane is a colorless, diamond-shaped solid that has good thermal stability and can be distilled via water vapor distillation process. It smells similar to camphor (C₁₀H₁₆O) and has a higher melting point than all other Hydrocarbons with similar molecular weights. It is the most simple diamondoid and is also a cycloalkane.
The actual adamantane molecule has three Cyclohexane rings (each ring is cycloalkane with a formula of C6H12) and is oriented in the "armchair" formation. The distance between the Hydrogen and Carbon in the molecule is about 1.112Å (Angstrom, which is 1/10,000,000,000 meters) and the length between the Carbons bonded is around 1.54Å-- this is almost the same as bonds in a diamond.
Synthesis / Occurrences
At a conference in the year 1924, H. Decker put forth the idea that there may be a Hydrocarbon with a molecular structure comparable to a diamond. This hypothetical molecule, dubbed "Decaterpene", would have the formula C10H16.
There was a lot of effort put in to try to synthesize this compound. Hans Meerwein used Piperidine to react Diethyl and Formaldehyde, but instead of the fabled "Decaterpene" got 1, 3, 5, 7-tetracarbomethoxybicyclo [3.3.1] nonane-2, 6-dione, which was named "Meerwein's Ester". It should be noted that Meerwein's Ester was actually used in the process of synthesizing not only adamantane, but all of its derivatives as well.
In 1932, adamantine was discovered amid crude oil via fractional distillation by V. Machacek and S. Landa. This relied on the constituents of the oil having differing boiling points. They heated the petroleum to the point where all impurities left behind were completely solid, and then the steam went through a fractional distillation column. The hydrocarbon fractions ended up condensing in the column at different points (according to each respective boiling point) due to the temperature decrease of the column. Very little of the substance was actually produced during this process, but everyone took note of the high boiling and melting point. However, it wasn't given much attention until the substance was synthesized by Vladimir Prelog in 1941. Prelog used a very complicated method in synthesizing adamantane from Meerwein's Ester from larger organic molecules. Thankfully, Paul von Ragué Schleyer accidentally discovered a much simpler process in 1959, a two-stage hydrogenation and restructuring process using dicyclopentadiene, a naptha derivative.
Derivatives of adamantane include:
- 2-Adamantanone or C10H14O
- 1-Acetamidoadamantane or C12H19NO
- 1,3-Dihydroxyadamantane (1,3-Adamantanediol) C10H16O2
- 2-Aminoadamantane Hydrochloride or C10H17NHC
- 1-Chloro-3,5- Dimethyladamantane or C12H19Cl
- 1-Adamantanemethanol (1-Adamantylmethanol) C11H18O
- 1-Adamantyl methyl ketone (1-Acetyladamantane) or C12H18O
- 2-Adamantanol (2-Hydroxyadamantane) or C10H16O
- 1-Aminoadamantane Sulfate ( Bis[1-Aminotricyclo (22.214.171.124.3.7)decane]sulfate) or (C10H17N)2H2SO4
- 1- Amino -3-Hydroxy –Adamantane or C10H17NO
One of the main uses for adamantane is in the medical realm. However, it should be noted that, in it's pure form, adamantane is never used medically. Only certain derivatives of this compound are used as antiviral medicines, including the treatment of Parkinson's disease and the Influenza A virus, as well as HIV, herpes, and hepatitis, however Swine Flu and H1N1 can resist adamantane-based antivirals. Derivative drugs include karmantadin, tromantadine, dopamantin, memantine, vildagliptin, and rinmantadine.
When it comes to influenza A, there is a membrane called M2, and it functions as an ion channel during some of the stages of replication inside the host cell of the virus. This is at the fusion of viral membrane and endosome membrane stages, which is when new virions are made and released. Thankfully, adamantine antivirals effectively block the ion channel, preventing any replication of the virus.
Possible Heath Issues
Like most other substances, adamantane can be harmful or irritating if exposed to certain areas or too much substance is used.
For humans, adamantane can irritate both the skin and eyes. In the case of exposure to the eyes, the compound should be washed out with a generous amount of water right away before going to a hospital for further treatment. Skin irritation isn't as serious, but should still be washed with soap and water immediately and the clothes that are affected should be washed before re-wearing. Now, if a person ingests adamantane, they are going to need to immediately get medical help. It is suggested that they drink 2-4 glasses of either milk or water so that the compound is diluted, but vomiting should not be forced or induced. And if the compound causes respiratory problems, then the person needs to get immediate medical assistance to receive oxygen or even artificial respiratory help. 
A video displaying the structure of adamantine.
- Adamantane Wikipedia. Web. Last modified 6 January, 2018. Authors unknown.
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- Clegg, Brian. Adamantane Chemistry World. Web. Published 26 January, 2017.
- Molecule of the Week Archive Adamantane American Chemical Society. Web. Last Updated October 5, 2017. Author Unknown.