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
Show more names
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
- Formal charge
- 0
- Complexity
- 144
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
- form
- Powder
- pka
- 10.1 · 10.1(at 25℃)
- color
- White to cream
- Water Solubility
- Soluble in organic solvents. Insoluble in water.
- Merck
- 14 · 14,374
- BRN
- 2204333 · 2204333
- Major Application
- food and beveragespersonal carepharmaceutical
- 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-
- InChIKey
- DKNWSYNQZKUICI-UHFFFAOYSA-N
- SMILES
- NC12C[C@H]3C[C@H](C[C@H](C3)C1)C2
- CAS DataBase Reference
- 768 · 768-94-5(CAS DataBase Reference)
- FDA UNII
- 4 C9Z1J53 · BF4C9Z1J53
- NCI Drug Dictionary
- Symadine
- ATC code
- 4 BB01 · N04BB01
- NIST Chemistry Reference
- 3.3 · Tricyclo[3.3.1.13,7]decane-1-amine(768-94-5)
- EPA Substance Registry System
- 3.3 · Tricyclo[3.3.1.13,7]decan-1-amine (768-94-5)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 301 · P301+P312+P330-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- RTECS
- 1925000 · YD1925000
- F
- 10 · 10-34
- TSCA
- TSCA listed
- HS Code
- 29213000 · 29213000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Hazardous Substances Data
- 768 · 768-94-5(Hazardous Substances Data)
- Toxicity
- 50 oral · LD50 oral in rat: 900mg/kg
- REACH Registrations
- Active
Safety & regulation
Safety data
- F
- 10-34
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- YD1925000
- hs_code
- 29213000
- Toxicity
- LD50 oral in rat: 900mg/kg
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P301+P312+P330-P302+P352-P305+P351+P338
- Hazardous Substances Data
- 768-94-5(Hazardous Substances Data)
Chemistry & industry
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A member of the class of adamantanes that is used as an antiviral and antiparkinson drug.
Related reactions
Linked notes
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