A1260

Amantadine hydrochloride

Name: Amantadine hydrochloride
Brand: SIGMA

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

Synonym(s):

1-Adamantanamine hydrochloride, 1-Adamantylamine hydrochloride, 1-Aminoadamantane hydrochloride, NSC 83653, Tricyclo[3.3.1.1^3,7]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

NACRES:

NA.77

PubChem Substance ID:

24277882

UNSPSC Code:

12352200

EC Number:

211-560-2

MDL number:

MFCD00074723

Beilstein/REAXYS Number:

4198854

Product Name

Amantadine hydrochloride,

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

SMILES string

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

form

powder

solubility

H₂O: 50 mg/mL
ethanol: soluble

originator

Endo

Quality Level

100

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Bioactive Small Molecules

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.

General description

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

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

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

0000461265

0000439459

WXBF5496V

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Medical complications during inpatient rehabilitation among patients with traumatic disorders of consciousness.

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)

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)

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)

Structure and inhibition of the drug-resistant S31N mutant of the M2 ion channel of influenza A virus.

Jun Wang et al.

Proceedings of the National Academy of Sciences of the United States of America, 110(4), 1315-1320 (2013-01-11)

The influenza A virus M2 proton channel (A/M2) is the target of the antiviral drugs amantadine and rimantadine, whose use has been discontinued due to widespread drug resistance. Among the handful of drug-resistant mutants, S31N is found in more than

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