Adamantane

• CAS: 281-23-2
• Catalog Number: ACM281232-1
• Category: Alkanes
• Molecular Weight: 136.23
• Molecular Formula: C10H16
• Synonyms: Tricyclo[3.3.1.13,7]decan
• IUPAC Name: Adamantane
• Canonical SMILES: C1C2CC3CC1CC(C2)C3
• InChI: InChI=1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2
• InChI Key: ORILYTVJVMAKLC-UHFFFAOYSA-N
• Melting Point: 209-212 °C
• Density: 1.07 g/ml
• Appearance: Powder
• Complexity: 75.1
• Covalently-Bonded Unit Count: 1
• EC Number: 206-001-4
• Exact Mass: 136.125201g/mol
• Formal Charge: 0
• Hazard Statements: H317
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Heavy Atom Count: 10
• LogP: 4.24 (LogP)
• Monoisotopic Mass: 136.125201g/mol
• NSC Number: 527913
• RIDADR: NONH for all modes of transport
• Rotatable Bond Count: 0
• Solubility In Water: Insoluble
• Symbol: GHS07
• UNII: PJY633525U
• XLogP3: 3.8

Case Study

Application Cases of Adamantane in Drug Delivery Systems and Surface Recognition

Štimac, Adela, et al. Molecules, 2017, 22(2), 297.

Adamantane is a highly symmetric and highly functional polycyclic cage-like molecule that has been widely used in the design and synthesis of novel drug delivery systems and in surface recognition studies. Some relevant research cases are listed below.
· Liposomes containing adamantane aminoguanidine:
Adamantane aminoguanidine derivatives have been reported to be successfully encapsulated in liposomes as model membrane systems. The size of liposomes containing incorporated adamantane aminoguanidine is similar to that of empty liposomes, but the surface charge of the guest-containing liposomes is significant, which confirms the anchor recognition site model. The proof-of-principle molecular recognition of this encapsulated adamantane aminoguanidine comes from probing the interaction of the liposomes.
· Adamantane cyclodextrin complexes:
Taking advantage of the strong interaction between adamantane and cyclodextrin and the ease of forming host-guest complexes, various cyclodextrin-based self-assembled systems have been developed for drug and gene delivery, as well as fluorescence sensing and bioimaging. Artificial glycocalyx on the surface of amphiphilic β-cyclodextrin vesicles can be used to study specific lectines, such as concanavalin A (ConA) in maltose and peanut agglutinin (PNA) in lactose.

Development of Catalysts Based on the Adamantane Framework

Agnew-Francis, Kylie A., et al. Advanced Synthesis & Catalysis, 2016, 358(5), 675-700.

The synthesis of di(1-adamantyl)phosphines can be achieved through the straightforward and cost-effective initial production of either Ad2PH or Ad2Cl, both of which are now available commercially. This synthesis was first documented by Gçrlich and Schmutzler in the mid-1990s, involving the reaction of adamantane with PCl3 and AlCl3 under Friedel-Crafts conditions, resulting in a 93% yield of Ad2P(O)Cl. This compound is then reduced at room temperature with HSiCl3 to yield Ad2PH (13) with 93% efficiency, which can subsequently undergo quantitative chlorination with CCl4 (see Scheme 2).
Constructing trialkylphosphines from these starting materials is easily accomplished by substituting alkyl halides with commercially available Ad2PH, typically yielding high product returns, especially with primary halides (approximately 90% yield). Purification often involves simply filtering out insoluble phosphonium salts, and the free phosphines can be recovered by treatment with triethylamine. Additionally, other methods, such as Beller's approach for synthesizing the commercially available Ad2PBu (15), utilize the corresponding chlorophosphine (i.e., 14) along with lithiated alkyl compounds (refer to Scheme 3).

Preliminary Synthesis Strategies of Multifunctional Adamantane Derivatives Used in Drug Development

Grillaud, Maxime, et al. Journal of Peptide Science, 2015, 21(5), 330-345.

A large number of monofunctional adamantane compounds have been studied, and they are mainly used as antiviral drugs. The four bridgehead positions of adamantane provide many possibilities for designing multifunctional derivatives.
Multi-functionalization of the Bridgehead Positions Starting from Adamantane Core
Stepwise functionalization of adamantane with halogens such as fluorine, chlorine, bromine and fluorine leads to products with bihalogenated, trihalogenated or tetrahalogenated configurations. The process permits various halogen insertion combinations before reaching the fully substituted 1-bromo-3-chloro-5-fluoro-7-iodoadamantane. By selecting proper conditions you can perform halogen exchange. The general protocol utilizes CH3I or CH2I2 solvents for iodine transfer while CH2Br2 or CHBr3 solvents serve bromine transfer purposes and CHCl3 or CCl4 solvents handle chlorine transfer.
The right table provides a summary of these tetra-functionalized adamantane derivatives, detailing their respective yields for each halogen in the bridgehead positions. A particularly notable compound is adamantane with four carboxylic acid groups (compound 7), which is valued for its water solubility and high reactivity, making it a versatile scaffold for constructing various tetravalent adamantane structures.

Custom Q&A

What is the PubChem CID for Adamantane?

PubChem CID: 9238

What is the molecular formula of Adamantane?

Molecular Formula: C10H16

What is the molecular weight of Adamantane?

Molecular Weight: 136.23 g/mol

What is the IUPAC Name of Adamantane?

IUPAC Name: Adamantane

What is the InChI of Adamantane?

InChI: InChI=1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2

What is the InChIKey of Adamantane?

InChIKey: ORILYTVJVMAKLC-UHFFFAOYSA-N

What is the Canonical SMILES of Adamantane?

Canonical SMILES: C1C2CC3CC1CC(C2)C3

What is the CAS number of Adamantane?

CAS: 281-23-2

What is the EC number of Adamantane?

EC Number: 206-001-4

What is the ChEMBL ID of Adamantane?

ChEMBL ID: CHEMBL1230831