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Sigma-Aldrich

Adamantane

≥99%

Synonym(s):

Tricyclo[3.3.1.13,7]decane

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About This Item

Empirical Formula (Hill Notation):
C10H16
CAS Number:
281-23-2
Molecular Weight:
136.23
Beilstein:
1901173
EC Number:
206-001-4
MDL number:
MFCD00074719
UNSPSC Code:
12352100
PubChem Substance ID:
24846519
NACRES:
NA.22

Assay

≥99%

form

solid

mp

209-212 °C (subl.) (lit.)

SMILES string

C1[C@H]2C[C@H]3C[C@@H]1C[C@@H](C2)C3

InChI

1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2/t7-,8+,9-,10+

InChI key

ORILYTVJVMAKLC-YNFQOJQRSA-N

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Application

Adamantane is the structural backbone of various medicinally important compounds such as amantadine, memantine, saxagliptin and vildagliptin. It is used in the synthesis of adamantine-based dirhodium tetracarboxylate catalyst for carbenoid reactions. It can also be used as a seeding material for the nucleation of nanocrystalline diamond films.

Hazard Statements

H413

Precautionary Statements

P273

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kenneth J Olejar et al.
Antioxidants (Basel, Switzerland), 8(7) (2019-07-25)
Valorization of agricultural waste has become increasingly important. Wastes generated by wineries are high in phenolic compounds with antioxidant and antibacterial properties, which contribute to phytotoxicity, making their immediate use for agricultural means limited. Utilizing a water-based extraction method, the
Ayako Takahashi et al.
American journal of physiology. Heart and circulatory physiology, 304(10), H1361-H1369 (2013-03-19)
Incretin hormones, including glucagon-like peptide-1 (GLP-1), a target for diabetes mellitus (DM) treatment, are associated with cardioprotection. As dipeptidyl-peptidase IV (DPP-IV) inhibition increases plasma GLP-1 levels in vivo, we investigated the cardioprotective effects of the DPP-IV inhibitor vildagliptin in a
Federico M Paruzzo et al.
Journal of magnetic resonance (San Diego, Calif. : 1997), 293, 41-46 (2018-06-12)
Coherence lifetimes in homonuclear dipolar decoupled 1H solid-state NMR experiments are usually on the order of a few ms. We discover an oscillation that limits the lifetime of the coherences by recording spin-echo dephasing curves. We find that this oscillation
Adamantane?a lead structure for drugs in clinical practice.
Spilovska K, et al.
Current Medicinal Chemistry, 23(29), 3245-3266 (2016)
The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives.
Lukas Wanka et al.
Chemical reviews, 113(5), 3516-3604 (2013-02-26)
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