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Sigma-Aldrich

Adamantane

≥99%

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Synonym(s):
Tricyclo[3.3.1.13,7]decane
Empirical Formula (Hill Notation):
C10H16
CAS Number:
281-23-2
Molecular Weight:
136.23
Beilstein:
1901173
EC Number:
206-001-4
MDL number:
MFCD00074719
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

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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
Nucleation enhancement of nanocrystalline diamond growth at low substrate temperatures by adamantane seeding.
Tsugawa K, et al.
The Journal of Physical Chemistry C, 114(9), 3822-3824 (2010)
Vlad Badilita et al.
PloS one, 7(8), e42848-e42848 (2012-09-01)
This article describes the development and testing of the first automatically microfabricated probes to be used in conjunction with the magic angle coil spinning (MACS) NMR technique. NMR spectroscopy is a versatile technique for a large range of applications, but
The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives.
Lukas Wanka et al.
Chemical reviews, 113(5), 3516-3604 (2013-02-26)
Adamantane?a lead structure for drugs in clinical practice.
Spilovska K, et al.
Current Medicinal Chemistry, 23(29), 3245-3266 (2016)
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