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A1260

Sigma-Aldrich

Amantadine hydrochloride

≥98% (TLC), powder, NMDA receptor antagonist

Synonym(s):

1-Adamantanamine hydrochloride, 1-Adamantylamine hydrochloride, 1-Aminoadamantane hydrochloride, NSC 83653, Tricyclo[3.3.1.13,7]decan-1-amine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C10H17N · HCl
CAS Number:
665-66-7
Molecular Weight:
187.71
Beilstein/REAXYS Number:
4198854
EC Number:
211-560-2
MDL number:
MFCD00074723
UNSPSC Code:
12352200
PubChem Substance ID:
24277882
NACRES:
NA.77

product name

Amantadine hydrochloride,

form

powder

Quality Level

100

solubility

H2O: 50 mg/mL
ethanol: soluble

originator

Endo

SMILES string

Cl[H].[H][C@@]12C[C@@]3([H])C[C@@]([H])(C1)CC(N)(C2)C3

InChI

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

InChI key

WOLHOYHSEKDWQH-SOVZANNPSA-N

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General description

Amantadine hydrochloride {tricyclo-[3,3,1,1]- deean-l-amine hydrochloride is a drug, which has rimantadine hydrochloride as its analog.

Application

Amantadine hydrochloride has been used:
  • to determine its effectiveness in reducing surgery-induced cognitive impairment
  • to preincubate multipotent stem cells (MSCs), to investigate the cellular internalization pathway
  • to determine whether amantadine-attenuated sepsis-induces neuroinflammation and dysfunction of learning and memory
  • to preincubate primary cultured rat dental pulp stem cells (rDPSCs)
  • to determine the pathway of internalization

Biochem/physiol Actions

Amantadine hydrochloride is effective against influenza viruses both in vivo and in vitro. It is considered as an antagonist of the N-methyl-D-aspartate (NMDA) type glutamate receptor. Amantadine plays an important role in the release of dopamine, preventing dopamine reuptake and blocking microglial activation and neuroinflammation.
Dopamine releaser used to treat Parkinsonism and drug-induced extrapyramidal reactions.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Endo. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Intracellular co-delivery of Sr ion and phenamil drug through mesoporous bioglass nanocarriers synergizes BMP signaling and tissue mineralization
Lee J H, et al.
Acta Biomaterialia, 93-108 (2017)
John Whyte et al.
Archives of physical medicine and rehabilitation, 94(10), 1877-1883 (2013-06-06)
To assess the incidence of medical complications in patients with recent traumatic disorders of consciousness (DOCs). Data on adverse events in a placebo controlled trial of amantadine hydrochloride revealed no group difference, which allowed these events to be reanalyzed descriptively
Amantadine attenuates sepsis-induced cognitive dysfunction possibly not through inhibiting toll-like receptor 2
Xing W, et al.
Journal of Molecular Medicine, 96(5), 391-402 (2018)
Amantadine ameliorates dopamine-releasing deficits and behavioral deficits in rats after fluid percussion injury
Huang E Y K, et al.
Testing, 9(1), e86354-e86354 (2014)
Rimantadine but not amantadine protects fischer rat embryo cells from transformation induced by 3-methylcholanthrene or benzo (a) pyrene
Price P J, et al.
In Vitro, 15(2), 82-85 (1979)
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