Amantadine

HCID 2130CAS 768-94-5

Basic information

Standard SMILES
NC12CC3CC(CC(C3)C1)C2
InChIKey
DKNWSYNQZKUICI-UHFFFAOYSA-N
Molecular formula
C10H17N
Average molar mass
151.25 g/mol
Monoisotopic mass
151.13609955

Names & identifiers

Preferred name
Amantadine
IUPAC
adamantan-1-amine
English name
Amantadine
Molecular formula
C10H17N
Molecular weight
151.25

Names & synonyms

amantadine1-Adamantanamine768-94-5adamantan-1-amine1-Adamantylamine1-AminoadamantaneAdamantanamineAdamantylamineAmantidineAminoadamantaneAdamantaminePk-merz
Show more names
(3s,5s,7s)-adaMantan-1-aMine
AmantadinaAmantadinumGocovriViregytNSC-341865DTXSID8022117Tricyclo[3.3.1.13,7]decan-1-amineTricyclo(3.3.1.1(sup 3.7))decan-1-amine

Database identifiers

CAS
768-94-5
PubChem CID
2130
DTXSID
DTXSID8022117
ChEMBL
CHEMBL660
ChEBI
CHEBI:2618
UNII
BF4C9Z1J53
EC Number
212-201-2
Nikkaji
J6.971J

Properties

Computed structural properties

XLogP
2.4
Topological polar surface area
26 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
11

Physicochemical properties

Melting point
206 · 206-208 °C(lit.)
Boiling point
263.29 °C · 263.29°C (rough estimate)
Density
0.951 · 0.9510 (rough estimate)
refractive index
1.522 · 1.5220 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
1 M · 1 M HCl: soluble5%, clear to hazy, colorless to faint yellow or tan

Safety & regulation

Safety data

F
10-34
wgk
3
tsca
TSCA listed
rtecs
YD1925000
hs_code
29213000
Toxicity
LD50 oral in rat: 900mg/kg

Chemistry & industry

Applications · 5 items

DescriptionAmantadine is an agent that raises the concentration of dopamine in the synaptic cleft by releasing it from neurons and suppressing the process of reuptake.

UsesBuilding block for an L-piperidinamide catalyst used in an enantioselective Strecker reaction of phosphinoyl imines.1

UsesAmantadine is a primary amine derivative of adamantane. It has an effect on mycoviruses, which are RNA-containing viruses. It has a very narrow spectrum of action and is used only for treating and preventing influenza A. It is also used for treating Parkinsonism. The exact mechanism of antiviral action of amantadine is not completely understood. It is believed that it is an ion channel blocker. It has also been suggested that amantadine inhibits absorption of viral particles into the host cell, which is expressed in the breakdown of diffusion of the virus into the cell, or inhibition of the “stripping process” of the virus. The main use is for the prevention of type A2 influenza. Synonyms of this drug are simmetrel, viregit, mantadan, and others.

UsesAmantadine is an antiviral drug. The properties in amantadine, which relieve symptoms of Parkinsonism were discovered by accident. Treatment of Parkinsonism with a combination of levodopa, anticholinergic drugs, and amantadine gives better results than using any of these drugs individually.

General DescriptionAmantadine has been used for years as a treatment for Parkinson disease. The adamantanamines have twomechanisms in common:they inhibit an early step in viralreplication, most likely viral uncoating,and in somestrains, they affect a later step that probably involves viral assembly,possibly by interfering with hemagglutinin processing.The main biochemical locus of action is the influenzatype A virus M2 protein, which is an integral membrane proteinthat functions as an ion channel. The M2 channel is a protontransport system. By interfering with the function of theM2 protein, the adamantanamines inhibit acid-mediated dissociationof the ribonucleoprotein complex early in replication.They also interfere with transmembrane proton pumping,maintaining a high intracellular proton concentrationrelative to the extracellular concentration and enhancingacidic pH-induced conformational changes in the hemagglutininduring its intracellular transport at a later stage. The conformationalchanges in hemagglutinin prevent transfer of thenascent virus particles to the cell membrane for exocytosis.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东海舟生物工程有限公司130-0567-0367 13006570367 · [email protected]

Additional notes

DefinitionChEBI: A member of the class of adamantanes that is used as an antiviral and antiparkinson drug.

Related reactions

161 records

Linked notes

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