Inhibitor
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Amantadine

Inhibitor
Product Name
Amantadine
CAS No.
768-94-5
Chemical Name
Amantadine
Synonyms
1-ADAMANTYLAMINE;Adamantylamine;1-ADAMANTANAMINE;Adamantamine;adamantan-1-amine;1-AMINOADAMANTANE;(3s,5s,7s)-adaMantan-1-aMine;Amantidine;ADAMANTANAMINE;Amanta
CBNumber
CB3259991
Molecular Formula
C10H17N
Formula Weight
151.25
MOL File
768-94-5.mol
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Amantadine Property

Melting point:
206-208 °C(lit.)
Boiling point:
263.29°C (rough estimate)
Density 
0.9510 (rough estimate)
refractive index 
1.5220 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
1 M HCl: soluble5%, clear to hazy, colorless to faint yellow or tan
form 
Powder
pka
10.1(at 25℃)
color 
White to cream
Water Solubility 
Soluble in organic solvents. Insoluble in water.
Merck 
14,374
BRN 
2204333
InChIKey
DKNWSYNQZKUICI-UHFFFAOYSA-N
CAS DataBase Reference
768-94-5(CAS DataBase Reference)
NIST Chemistry Reference
Tricyclo[3.3.1.13,7]decane-1-amine(768-94-5)
EPA Substance Registry System
Tricyclo[3.3.1.13,7]decan-1-amine (768-94-5)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
YD1925000
10-34
HS Code 
29213000
Hazardous Substances Data
768-94-5(Hazardous Substances Data)
Toxicity
LD50 oral in rat: 900mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
138576
Product name
1-Adamantylamine
Purity
97%
Packaging
5g
Price
$90.4
Updated
2024/03/01
Sigma-Aldrich
Product number
138576
Product name
1-Adamantylamine
Purity
97%
Packaging
25g
Price
$280
Updated
2024/03/01
TCI Chemical
Product number
A2318
Product name
1-Adamantanamine
Purity
>98.0%(GC)(T)
Packaging
5g
Price
$81
Updated
2024/03/01
TCI Chemical
Product number
A2318
Product name
1-Adamantanamine
Purity
>98.0%(GC)(T)
Packaging
25g
Price
$272
Updated
2024/03/01
Alfa Aesar
Product number
H30076
Product name
1-Adamantanamine, 98%
Packaging
5g
Price
$56.5
Updated
2024/03/01
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Amantadine Chemical Properties,Usage,Production

Inhibitor

The anti-influenza A compound amantadine acts by blocking the M2 ion channel which is required for uptake of protons into the interior of the virus to permit acid-promoted viral uncoating (decapsidation).

Description

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

Chemical Properties

White to cream powder

Uses

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

Uses

Amantadine 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.

Uses

Amantadine 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.

Definition

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

brand name

Symadine (Solvay Pharmaceuticals); Symmetrel (Endo).

Biological Functions

Amantadine was originally introduced as an antiviral compound, but it is modestly effective in treating symptoms of parkinsonism. It is useful in the early stages of parkinsonism or as an adjunct to levodopa therapy. Its mechanism of action in parkinsonism is not clear, but amantadine may affect dopamine release and reuptake. Additional sites of action may include antagonism at muscarinic and N-methyl-Daspartate (NMDA) receptors. Adverse effects include nausea, dizziness, insomnia, confusion, hallucinations, ankle edema, and livedo reticularis. Amantadine and the anticholinergics may exert additive effects on mental functioning

Synthesis Reference(s)

Journal of the American Chemical Society, 91, p. 6457, 1969 DOI: 10.1021/ja01051a047
Synthesis, p. 457, 1976

Antimicrobial activity

It inhibits influenza A virus replication at concentrations of 0.2– 0.6 mg/L, but has little or no activity against influenza B or C.

Acquired resistance

Resistance is the consequence of mutations in amino acid positions 27, 30 and 31 in the M2 transmembrane sequence. Cross-resistance between amantadine and rimantadine is universal. Influenza H3N2 strains worldwide are now resistant, but seasonal H1N1 strains remain susceptible. Postexposure family prophylaxis results in the prompt emergence of drug resistance after onset of treatment.

General Description

Amantadine 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.

Flammability and Explosibility

Flammable

Pharmaceutical Applications

A symmetrical synthetic C-10 tricyclic amine with an unusual cage-like structure, supplied as the hydrochloride for oral administration.

Mechanism of action

Amantadine hydrochloride (1-adamantanamine hydrochloride) is a symmetric, tricyclic, primary amine that inhibits penetration of RNA viral particles into the host cell. It also inhibits the early stages of viral replication by blocking the uncoating of the viral genome and the transfer of nucleic acid into the host cell.

Pharmacokinetics

Oral absorption: >90%
Cmax 200 mg oral per day: 0.4–0.9 mg/L after c. 4–6 h
Plasma half-life: 9.7–14.5 h
Volume of distribution: 10.4 L/kg
Plasma protein binding: 65%
Absorption and distribution
Absorption after oral administration is almost complete. Levels in secretions approach plasma concentrations.
Metabolism and excretion
About 56% of a single oral dose is excreted unchanged within 24 h by the kidney. Altogether 90% of an oral dose is excreted in the urine with a mean elimination half-life of 11.8 h in subjects with normal renal function. In elderly men, the half-life is 28.9 h and in patients with renal insufficiency half-lives of 18.5 h to 33.8 days have been observed. The renal clearance is around 398 mL/min (range 112–772 mL/min), indicating active secretion as well as glomerular filtration. Less than 5% of a dose is removed during hemodialysis and average half-lives of 8.3 and 13 days have been reported in patients on chronic hemodialysis. Extreme care must be taken to ensure that drug does not accumulate to toxic levels.

Clinical Use

Prevention and treatment of influenza A H1N1 infections

Clinical Use

Amantadine is used for the treatment of diseases caused by influenza A strains.

Side effects

Embryotoxicity and teratogenicity have been observed in rats receiving 50 mg/kg per day, about 15 times the usual human dose. Neurological side effects include drowsiness, insomnia, light-headedness, difficulty in concentration, nervousness, dizziness and headache in up to 20% of individuals. Other side effects include anorexia, nausea, vomiting, dry mouth, constipation and urinary retention. All develop during the first 3–4 days of therapy and are reversible by discontinuing the drug. An exception to rapid onset of adverse reactions is livedo reticularis. Convulsions, hallucinations and confusion are dose related, usually occurring at levels in excess of 1.5 mg/L; convulsions may occur at a lower threshold in patients with a history of epilepsy and the drug is best avoided in such patients.

Safety Profile

Poison by intraperitoneal route.Moderately toxic by ingestion. Mutation data reported.When heated to decomposition it emits toxic fumes ofNOx. Used as an antiviral agent.

Synthesis

Amantadine, 1-adamantanamine (10.1.12), is synthesized from adamantane. It is directly brominated to 1-bromadamantane (10.1.10), which in Ritter reaction conditions when heated with a mixture of acetonitrile and concentrated sulfuric acid transforms into 1-acetylaminoadamantane (10.1.11). Hydrolysis of this product using alkali leads to the formation of amantadine (10.1.12) [16,17].

Purification Methods

Dissolve the amine in Et2O, dry it over KOH, evaporate and sublime it in vacuo. [Stetter et al. Chem Ber 93 226 1960.]

Amantadine Preparation Products And Raw materials

Raw materials

Preparation Products

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Amantadine Suppliers

Sichuan Zhongbang Pharma CO.,LTD
Tel
0830-0830-2585019 13679670161
Fax
0830-2589033
Email
sales2@zhongbangst.com
Country
China
ProdList
105
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69
Wuxi Helen Biotechnology Co., Ltd.,
Tel
0510-85629785 18013409632
Fax
0510-85625359
Email
sales@reading-chemicals.com
Country
China
ProdList
14081
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58
Taian Jiayue Bio-chemical Co. LTD
Tel
15318151873
Email
285424065@qq.com
Country
China
ProdList
4548
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58
Shandong Haizhou Biological Engineering Co. LTD
Tel
130-0567-0367 13006570367
Email
3429531746@qq.com
Country
China
ProdList
2456
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
021-50182298 021-50180596
Fax
+86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2208
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J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
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INTATRADE GmbH
Tel
+49 3493/605464
Fax
+49 3493/605470
Email
sales@intatrade.de
Country
Germany
ProdList
3572
Advantage
66
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
future industrial shanghai co., ltd
Tel
400-0066400 13621662912
Fax
021-55660885
Email
sales@jonln.com
Country
China
ProdList
1995
Advantage
65
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View Lastest Price from Amantadine manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Amantadine 768-94-5
Price
US $980.00-750.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-15
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Amantadine 768-94-5
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98%min
Supply Ability
1000kg
Release date
2021-10-21
Hebei Dangtong Import and export Co LTD
Product
Amantadine 768-94-5
Price
US $50.00-45.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
8000kg
Release date
2023-09-15

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