Structure via PubChem · Public domain (PubChem)
adamantane
Sign in to saveAdamantane is an organic compound with formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually strain-free. Adamantane is the most stable isomer of C10H16. The spatial arrangement of carbon atoms in the adamantane molecule is the same as in the diamond crystal. This similarity led to the name adamantane, which is derived from the Greek adamantinos (relating to steel or diamond). It is a white solid with a camphor-like odor. It is the simplest diamondoid.
Chemical data
- Formula
- C10H16
- Molecular weight
- 136.23 g/mol
- IUPAC name
- adamantane
- SMILES
- C1C2CC3CC1CC(C2)C3
- InChIKey
- ORILYTVJVMAKLC-UHFFFAOYSA-N
- XLogP
- 3.8
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Research
13,341 papers- Nascent pharmacological advancement in adamantane derivatives.Archiv der Pharmazie · 2024
- The adamantane scaffold: Beyond a lipophilic moiety.European journal of medicinal chemistry · 2025
- Adamantane in Drug Delivery Systems and Surface Recognition.Molecules (Basel, Switzerland) · 2017
- Adamantane - A Lead Structure for Drugs in Clinical Practice.Current medicinal chemistry · 2016
- Potential for the Repurposing of Adamantane Antivirals for COVID-19.Drugs in R&D · 2021
via PubMed
Wikidata facts
- Mass
- 136.125
Show 6 more facts
- canonical SMILES
- C1C2CC3CC1CC(C2)C3
- Commons category
- Adamantane
- chemical formula
- C₁₀H₁₆
- melting point
- 267
- standard enthalpy of formation
- -197.2
- refractive index
- 1.568
Sources (7)
via Wikidata · CC0
~18 min read
Article
18 sectionsContents
- History and synthesis
- Natural occurrence
- Physical properties
- Structure
- Hardness
- Spectroscopy
- Optical activity
- Nomenclature
- Chemical properties
- Bridgehead reactions
- Substitution at bridging carbons
- Uses
- In medicine
- In designer drugs
- Spacecraft propellant
- Potential technological applications
- Adamantane analogues
- References
Adamantane is an organic compound with formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually strain-free. Adamantane is the most stable isomer of C10H16. The spatial arrangement of carbon atoms in the adamantane molecule is the same as in the diamond crystal. This similarity led to the name adamantane, which is derived from the Greek adamantinos (relating to steel or diamond). It is a white solid with a camphor-like odor. It is the simplest diamondoid.
The discovery of adamantane in petroleum in 1933 launched a new field of chemistry dedicated to the synthesis and properties of polyhedral organic compounds. Adamantane derivatives have found practical application as drugs, polymeric materials, and thermally stable lubricants.