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Amantadine

Inhibitor
Amantadine
Amantadine structure
CAS No.
768-94-5
Chemical Name:
Amantadine
Synonyms
C06818;Amanta;Pk-Merz;Symadine;Amantadin;Mantadine;Amantidine;AMANTADINE;NSC 341865;AMANTADINA
CBNumber:
CB3259991
Molecular Formula:
C10H17N
Formula Weight:
151.25
MOL File:
768-94-5.mol

Amantadine Properties

Melting point:
206-208 °C(lit.)
Boiling point:
263.29°C (rough estimate)
Density 
0.9510 (rough estimate)
refractive index 
1.5220 (estimate)
solubility 
1 M HCl: soluble5%, clear to hazy, colorless to faint yellow or tan
pka
10.1(at 25℃)
form 
Powder
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)
FDA UNII
BF4C9Z1J53
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)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P280a-P304+P340-P405-P501a-P264-P270-P280-P301+P312+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P501-P261-P305+P351+P338
Hazard Codes  Xn,Xi
Risk Statements  22-36/37/38
Safety Statements  26-36
WGK Germany  3
RTECS  YD1925000
10-34
HS Code  29213000
Toxicity LD50 oral in rat: 900mg/kg

Amantadine price More Price(10)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 138576 1-Adamantylamine 97% 768-94-5 5g $37.2 2020-08-18 Buy
Sigma-Aldrich 138576 1-Adamantylamine 97% 768-94-5 25g $175 2020-08-18 Buy
TCI Chemical A2318 1-Adamantanamine >98.0%(GC)(T) 768-94-5 5g $80 2020-06-24 Buy
TCI Chemical A2318 1-Adamantanamine >98.0%(GC)(T) 768-94-5 25g $253 2020-06-24 Buy
Alfa Aesar H30076 1-Adamantanamine, 98% 768-94-5 5g $44.1 2020-06-24 Buy

Amantadine Chemical Properties,Uses,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).

Chemical Properties

White to cream powder

Uses

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

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.

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.

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


Amantadine Suppliers

Global( 281)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22624 55
Shanghai Time Chemicals CO., Ltd.
+86-021-57951555
+86-021-57951555 jack.li@time-chemicals.com CHINA 1365 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 30039 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28231 58
QUALITY CONTROL CHEMICALS INC.
(323) 306-3136
(626) 453-0409 orders@qcchemical.com United States 8406 58
Standardpharm Co. Ltd.
86-714-3992388
overseasales1@yongstandards.com United States 14344 58
Chongqing Chemdad Co., Ltd
+86-13650506873
sales@chemdad.com CHINA 35434 58
Alchem Pharmtech,Inc.
8485655694
sales@alchempharmtech.com United States 63728 58
CONIER CHEM AND PHARMA LIMITED
86-18523575427
sales@conier.com CHINA 47486 58
Zhuozhou Wenxi import and Export Co., Ltd
+8613111626072
+8613111626072 zzwenxi@126.com CHINA 7507 58

View Lastest Price from Amantadine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2020-04-01 Amantadine; 1-Adamantanamine; 1-Aminoadamantane; Tricyclo[3.3.1.1(3,7)]decane-1-amine
768-94-5
US $0.00 / KG 10KG 99% 10mt Chengdu Yuanda Chemical Co., Ltd
2018-08-13 Amantadine
768-94-5
US $1.00 / KG 1KG 98% 1ton career henan chemical co

Amantadine Spectrum


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