ChemicalBook Product Catalog Organic Chemistry Organosulfur compounds 1-Adamantanamine sulfate

1-Adamantanamine sulfate

Product Name1-Adamantanamine sulfate
CAS31377-23-8
MFC10H19NO4S
MW249.33
EINECS250-604-5
MOL File31377-23-8.mol

Chemical Properties

Melting point	300 °C
storage temp.	Store below +30°C.
solubility	Aqueous Acid (Slightly), Aqueous Base (Slightly)
form	Fine Crystalline Powder
color	White
PH	4.9 (100g/l, H2O, 20°C) (slurry)
Stability	Hygroscopic
InChI	InChI=1S/C10H17N.H2O4S/c11-10-4-7-1-8(5-10)3-9(2-7)6-10;1-5(2,3)4/h7-9H,1-6,11H2;(H2,1,2,3,4)
InChIKey	MYWTWSQFJLXGGQ-JUMAMQMDSA-N
SMILES	NC12CC3CC(CC(C3)C1)C2.S(O)(O)(=O)=O
CAS DataBase Reference	31377-23-8(CAS DataBase Reference)

Safety Information

Safety Statements	24/25
WGK Germany	WGK 3 highly water endangering
HS Code	2921 30 99
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
ACROS	English

Usage And Synthesis

Preparation

Amantadine hydrochloride was dissolved in distilled water, and sodium sulfate solution (anhydrous sodium sulfate dissolved in distilled water) was added dropwise with stirring at room temperature. A large amount of white precipitate was formed. After the addition was complete, the solution was filtered, washed with water, and dried to obtain 1-ADAMANTANAMINE SULFATE.

Chemical Properties

white fine crystalline powder

Uses

Amantadine (1-Adamantanamine) sulfate is an orally avtive and potent antiviral agent with activity against influenza A viruses. Amantadine sulfate inhibits several ion channels such as NMDA and M2, and also inhibits Coronavirus ion channels. Amantadine sulfate also has anti-orthopoxvirus and anticancer activity. Amantadine sulfate can be used for Parkinson's disease, postoperative cognitive dysfunction (POCD) and COVID-19 research[1][2][3][4][5][6].

Definition

ChEBI: An alkylammonium sulfate salt obtained by combining amantadine and sulfuric acid in a 2:1 ratio. Used as an antiviral and antiparkinson drug.

in vivo

Amantadine sulfate (25 mg/kg, IP, once daily for 3 days) inhibits surgery induced neuroinflammation and learning and memory impairment^[5].

Animal Model:	Fischer 344 rats (Four-month old, male, 290-330 g, 15 rats each group)^[5]
Dosage:	25 mg/kg
Administration:	IP, once daily for 3 days (the first dose at 15 min before surgery)
Result:	Inhibited surgery induced neuroinflammation and learning and memory impairment, increased GDNF (glial cell line-derived neurotrophic factor) that was co-localized with glial fibrillary acidic protein (an astrocytic marker) in the hippocampus.

IC 50

CDK2; Bcl-2; Bax

References

[1] Suzuki H, et al. Emergence of amantadine-resistant influenza A viruses: epidemiological study. J Infect Chemother. 2003;9(3):195-200. DOI:10.1007/s10156-003-0262-6
[2] Hubsher G, et al. Amantadine: the journey from fighting flu to treating Parkinson disease. Neurology. 2012;78(14):1096-1099. DOI:10.1212/WNL.0b013e31824e8f0d
[3] Donald F Smee, et al. A review of compounds exhibiting anti-orthopoxvirus activity in animal models. Antiviral Res. 2003 Jan;57(1-2):41-52. DOI:10.1016/s0166-3542(02)00199-7
[4] Fink K, et al. Amantadine Inhibits SARS-CoV-2 In Vitro. Viruses. 2021 Mar 24;13(4):539. DOI:10.3390/v13040539
[5] Zhang J, et al. Amantadine alleviates postoperative cognitive dysfunction possibly by increasing glial cell line-derived neurotrophic factor in rats. Anesthesiology. 2014 Oct;121(4):773-85. DOI:10.1097/ALN.0000000000000352
[6] Lan Z, et al. Amantadine inhibits cellular proliferation and induces the apoptosis of hepatocellular cancer cells in vitro. Int J Mol Med. 2015;36(3):904-910. DOI:10.3892/ijmm.2015.2289

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