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Merck

138576

1-Adamantylamine

97%

Synonym(s):

1-Aminoadamantane

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About This Item

Empirical Formula (Hill Notation):
C10H17N
CAS Number:
768-94-5
Molecular Weight:
151.25
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24848359
EC Number:
212-201-2
Beilstein/REAXYS Number:
2204333
MDL number:
MFCD00074732

Product Name

1-Adamantylamine, 97%

InChI key

DKNWSYNQZKUICI-CHIWXEEVSA-N

InChI

1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2/t7-,8+,9-,10-

SMILES string

NC12C[C@H]3C[C@H](C[C@H](C3)C1)C2

assay

97%

mp

206-208 °C (lit.)

solubility

1 M HCl: soluble 5%, clear to hazy, colorless to faint yellow or tan

Quality Level

200

Gene Information

human ... GRIN2A(2903)

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Application

1-Adamantylaminecan be used as a reactant to synthesize:
  • Adamantyl ureas by reacting with isocyanates in the presence of triethylamine.
  • N-(1-adamantyl)-2-chloroacetamide from chloroacetyl chloride in the presence of potassium carbonate.

General description

1-Adamantylamine, also known as Amantadine, is an adamantane derivative where an amino group is replaced by one of the methyl groups of adamantane. It is commonly used as a starting material in various organic reaction, such as monomer synthesis and one-pot synthesis of 1-adamantylhydrazine.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW8663
MKCW8255
0000227068
MKCS5254
MKCT4661

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Jinglun Huang et al.
The Journal of organic chemistry, 72(1), 204-208 (2006-12-30)
The enantioselective Strecker reaction of N-diphenylphosphinoyl ketoimines has been achieved by use of in situ prepared chiral N,N'-dioxide catalyst from l-piperidinamide 3f and m-chloroperoxybenzoic acid (m-CPBA). Excellent yields (up to 99%) and high enantioselectivities (up to 92% ee) were obtained.
Lei Deng et al.
Nature communications, 9(1), 359-359 (2018-01-26)
Current influenza vaccines provide limited protection against circulating influenza A viruses. A universal influenza vaccine will eliminate the intrinsic limitations of the seasonal flu vaccines. Here we report methodology to generate double-layered protein nanoparticles as a universal influenza vaccine. Layered
Terminal Modification with 1-Adamantylamine to Endow Hyperbranched Polyamidoamine with Thermo-/pH-Responsive Properties.
Guo Z, et al.
Macromolecular Rapid Communications, 29(21), 1746-1751 (2008)
Márió Gajdács et al.
Antibiotics (Basel, Switzerland), 8(4) (2019-12-22)
Background: The emergence of multidrug-resistant organisms (MDROs) is a global public health issue, severely hindering clinicians in administering appropriate antimicrobial therapy. Drug repurposing is a drug development strategy, during which new pharmacological applications are identified for already approved drugs. From
Torsten Arndt et al.
Clinica chimica acta; international journal of clinical chemistry, 359(1-2), 125-131 (2005-05-26)
Amantadine (1-adamantylamine) is used for treatment of influenza, hepatitis C, parkinsonism, and multiple sclerosis. Current amantadine analysis by HPLC or gas chromatography (GC) requires a laborious sample pretreatment with extraction and/or derivatization steps. We established an LC-MS/MS method without protein
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