ChemicalBook >> CAS DataBase List >>1-Adamantanamine hydrochloride

1-Adamantanamine hydrochloride

CAS No.
665-66-7
Chemical Name:
1-Adamantanamine hydrochloride
Synonyms
AMANTADINE HCL;AMANTADINE HYDROCHLORIDE;1-AMINOADAMANTANE HYDROCHLORIDE;symmetrel;1-ADAMANTANAMINE HCL;Mantadan;ADAMANTANAMINE HYDROCHLORIDE;Amantadine hydrochloride,1-Adamantanamine hydrochloride, 1-Adamantylamine hydrochloride, 1-Aminoadamantane hydrochloride;Adekin;virasol
CBNumber:
CB4734376
Molecular Formula:
C10H18ClN
Molecular Weight:
187.71
MDL Number:
MFCD00074723
MOL File:
665-66-7.mol
MSDS File:
SDS
Modify Date:2023-02-01 17:21:24

1-Adamantanamine hydrochloride Properties

Melting point >300 °C(lit.)
Boiling point 308.63°C (rough estimate)
Density 1.0276 (rough estimate)
refractive index 1.6100 (estimate)
storage temp. Store below +30°C.
solubility H2O: 50 mg/mL
form Fine Crystalline Powder
color White
Water Solubility soluble
Sensitive Hygroscopic
Merck 14,374
BRN 4198854
InChIKey WOLHOYHSEKDWQH-UHFFFAOYSA-N
LogP -1.64 at 23℃ and pH6.3
CAS DataBase Reference 665-66-7(CAS DataBase Reference)
FDA UNII M6Q1EO9TD0
NCI Dictionary of Cancer Terms amantadine hydrochloride
NCI Drug Dictionary amantadine hydrochloride
Proposition 65 List Amantadine Hydrochloride
EPA Substance Registry System Amantadine hydrochloride (665-66-7)

Pharmacokinetic data

Protein binding 67%
Excreted unchanged in urine 90%
Volume of distribution 5-10(L/kg)
Biological half-life 15 / 500

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P301+P312+P330
Hazard Codes  Xn
Risk Statements  22-40-20/21/22
Safety Statements  22-36/37-36-35-20/21
RIDADR  UN 1759 8 / PGII
WGK Germany  3
RTECS  AU4375000
TSCA  Yes
HazardClass  IRRITANT
HS Code  29213000
Toxicity LD50 orally in mice, rats: 700, 1275 mg/kg (Vernier)
NFPA 704
1
3 0

1-Adamantanamine hydrochloride price More Price(51)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A1260 Amantadine hydrochloride 665-66-7 5g $64.3 2023-01-07 Buy
Sigma-Aldrich BP530 Amantadine hydrochloride British Pharmacopoeia (BP) Reference Standard 665-66-7 200MG $254 2023-01-07 Buy
Sigma-Aldrich 8.20015 1-Adamantaneammonium chloride for synthesis 665-66-7 10g $62.5 2023-01-07 Buy
Sigma-Aldrich 8.20015 1-Adamantaneammonium chloride for synthesis 665-66-7 50g $228 2023-01-07 Buy
Sigma-Aldrich 1018505 Amantadine hydrochloride United States Pharmacopeia (USP) Reference Standard 665-66-7 200mg $400 2022-05-15 Buy
Product number Packaging Price Buy
A1260 5g $64.3 Buy
BP530 200MG $254 Buy
8.20015 10g $62.5 Buy
8.20015 50g $228 Buy
1018505 200mg $400 Buy

1-Adamantanamine hydrochloride Chemical Properties,Uses,Production

Chemical Properties

Crystalline Solid

Originator

Symmetrel,DuPont (Endo),US,1966

Uses

selective FP prostanoid receptor agonist, F-series prostaglandin analog. 200 times as potent as Latanoprost -20oC

Uses

antiviral, antiparkinsonian; treatment of drug-induced extrapyrimidal reactions

Uses

NMDA-receptor antagonist. Antiviral; antiparkinsonian

Uses

1-Adamantanamine hydrochloride is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extra pyramidal reactions, and for postherpetic neuralgia. It is also used an NMDA-receptor antagoinst.

Definition

ChEBI: A hydrochloride obtained by combining amantadine and hydrochloric acid in equimolar amounts.

Manufacturing Process

360 ml of 96% sulfuric acid and a solution of 13.6 grams (0.1 mol) of adamantane in 100 ml of n-hexane were emulsified in the apparatus described and provided with an inclined centrifugal stirrer. Then a mixture of 46 grams (1.7 mols) of liquid hydrocyanic acid and 29.6 grams (0.4 mol) of tertiary butanol was added dropwise within 1.5 hours at about 25°C.
After 30 minutes of postreaction, the product was poured on ice. The granular mass which precipitated [N-(adamantyl-1)formamide] was sucked off and washed with water. The raw product (37 grams) was then refluxed for 10 hours with a solution of 60 grams of NaOH in 600 ml of diethylene glycol.
After cooling, the solution was diluted with 1.5 liters of water and subjected to three extractions with ether. The amine was extracted from the ethereal solution with 2 N HCl and liberated therefrom by the addition of solid NaOH (while cooling). The alkaline solution was extracted with ether and the ethereal solution was dried with solid NaOH. Distillation resulted in 10.6 grams (70% of the theory) of 1-aminoadamantane which, after sublimation, melted at 180°C to 192°C (seal capillary). It is converted to the hydrochloride.

brand name

Symadine (Solvay Pharmaceuticals); Symmetrel (Endo).

Therapeutic Function

Antiviral, Antiparkinsonian

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Biological Activity

amantadine hydrochloride is an antiviral and an antiparkinsonian drug.

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.

Clinical Use


Parkinson’s disease (but not drug-induced extrapyramidal symptoms)
Post-herpetic neuralgia
Prophylaxis and treatment of influenza A

Safety Profile

Human poison by ingestion. Poison by ingestion, intraperitoneal, and intravenous routes. A human teratogen with developmental abnormalities of the circulatory system. Experimental reproductive effects. Human systemic effects by ingestion: distorted perceptions, euphoria, excitement, hallucinations. When heated to decomposition it emits very toxic fumes of NO, and HCl.

Drug interactions

Potentially hazardous interactions with other drugs
Memantine: increased risk of CNS toxicity - avoid; effects of amantadine possibly enhanced.

Metabolism

Amantadine is metabolised in the liver to a minor extent, mainly by N-acetylation. The renal amantadine clearance is much higher than the creatinine clearance, suggesting renal tubular secretion in addition to glomerular filtration. After 4-5 days, 90% of the dose appears unchanged in urine. The rate is considerably influenced by urinary pH: a rise in pH brings about a fall in excretion.

Purification Methods

Dissolve the salt in dry EtOH, add a few drops of dry EtOH saturated with HCl gas, followed by dry Et2O to crystallise the hydrochloride. Dry the salt in a vacuum. [Stetter et al. Chem Ber 93 226 1960.]

Global( 594)Suppliers
Supplier Tel Email Country ProdList Advantage
Hangzhou Qiwei Pharmatech Co.,Ltd
13282840061 mw@qwpharmatech.com China 109 58
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806 sales@capotchem.com China 29801 60
Henan DaKen Chemical CO.,LTD.
+8613027611063 info@dakenchem.com China 17366 58
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497 sales01@cooperate-pharm.com CHINA 1811 55
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233 +86-13795318958 Candy@bj-chem.com China 298 55
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21975 55
Shanghai Time Chemicals CO., Ltd.
+86-021-57951555 +8617317452075 jack.li@time-chemicals.com China 1807 55
Guangzhou PI PI Biotech Inc
+86-020-81716320 +86-18371201331 Sales@pipitech.com China 3635 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070 product@chemlin.com.cn CHINA 3012 60
Hubei XinRunde Chemical Co., Ltd.
+8615102730682 bruce@xrdchem.cn CHINA 566 55

View Lastest Price from 1-Adamantanamine hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
1-Adamantanamine hydrochloride pictures 2023-02-02 1-Adamantanamine hydrochloride
665-66-7
US $0.00-0.00 / KG 1KG 99% 500000kg Hebei Guanlang Biotechnology Co., Ltd.
1-Adamantanamine hydrochloride pictures 2023-01-31 1-Adamantanamine hydrochloride
665-66-7
US $50.00 / KG 1KG 99% 5000KG Hebei Mojin Biotechnology Co., Ltd
Amantadine Hydrochloride pictures 2023-01-30 Amantadine Hydrochloride
665-66-7
US $10.70 / Kg/Bag 10g 99% 10000kg Hebei Crovell Biotech Co Ltd
Amantadine Hydrochloride (200 mg) 1-AdaMantanaMine hydrochloride, 99+% 100GR 1-AdaMantanaMine hydrochloride, 99+% 25GR 1-AdaMantanaMine hydrochloride, 99+% 5GR 1-adamantane amine hydrochloride 1-Adamantanamine Hydrochleride 1-Aminoadamantane Hydrochloride Amantadine Hydrochloride Adamantan-1-amine hydrochloride, Tricyclo[3.3.1.1~3,7~]decan-1-amine hydrochloride, Amantadine hydrochloride AMantadine HCl USP 1-adamantylammonium chloride 1-adamantylazanium chloride 1-Aminoadamantene hydrochlorid adamantan-1-aminium chloride tricyclo[3.3.1.1(3,7)]decan-1-aminium chloride Tricyclo[3.3.1.13,7]decan-1-amine, hydrochloride (1:1) aminoadamantanehydrochloride exp105-1 midantane mydantane nsc83653 tricyclo(3.3.1.1(sup3,7))decan-1-amine,hydrochloride 1-Adamantanamine hydrochloride, 1-Adamantylamine hydrochloride, Amantadine hydrochloride 1-Adamantanamine hydrochloride, 1-Adamantylamine hydrochloride, 1-Aminoadamantane hydrochloride TIMTEC-BB SBB003680 TRICYCLODECANE HYDROCHLORIDE ADAMANTAN-1-AMINE HYDROCHLORIDE 1-aminoadamantenehydrochloride 1-ADAMANTYLAMINE HYDROCHLORIDE 1-ADAMANTANAMINE HYDROCHLORIDE 1-ADAMANTANEAMMONIUM CHLORIDE adamantinehydrochloride adamantylaminehydrochloride tricyclo[3.3.1.13,7]decan-1-amine,hydrochloride virasol AMANTADINE HYDROCHLORIDE, PHARMA Adekin Lysovir Mantadix Virofral AMANTADINEHYDROCHLORIDE,USP 1-Adamantamine hydrochloride 1-Adamantanamine, hydrochloride (8CI) Adamantanamine hydrochloride (6CI) Amazolon Midantan 1-ADAMANTANAMINE HYDROCHLORIDE, 99+% 1-Adamantaneammonium chloride for synthesis 1-Adamantanamin Hydrochlorid 1-Adamantanamine HydrochL 1-adamantylammonium Adamantane Hydrocloride 1-Adamantanamine hydrochloride intermediate 1-Adamantanamine Hydrochloride [Amantadine Hydrochloride] Amintadine Hcl 1-Amantadine hydrochloride (3s,5s,7s)-adamantan-1-amine hydrochloride 1-Adamantanamine hydrochloride, 99%, antiviral and antiparkinsonian compound Memantine Impurity 13