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1-Adamantanamine hydrochloride

1-Adamantanamine hydrochloride Structure
1-Adamantanamine hydrochloride structure
CAS No.
665-66-7
Chemical Name:
1-Adamantanamine hydrochloride
Synonyms
AMANTADINE HCL;AMANTADINE HYDROCHLORIDE;1-AMINOADAMANTANE HYDROCHLORIDE;ADAMANTANAMINE HYDROCHLORIDE;symmetrel;1-ADAMANTANAMINE HCL;ADAMANTAN-1-AMINE HYDROCHLORIDE;Mantadan;Amantadine hydrochlorid;(3s,5s,7s)-adamantan-1-amine hydrochloride
CBNumber:
CB4734376
Molecular Formula:
C10H18ClN
Molecular Weight:
187.71
MDL Number:
MFCD00074723
MOL File:
665-66-7.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-07-27 17:00:41
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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
pka 10.71
color White
Water Solubility soluble
Sensitive Hygroscopic
Merck 14,374
BRN 4198854
Major Application pharmaceutical (small molecule)
InChI 1S/C10H17N.ClH/c11-10-4-7-1-8(5-10)3-9(2-7)6-10;/h7-9H,1-6,11H2;1H/t7-,8+,9-,10-;
InChIKey WOLHOYHSEKDWQH-UHFFFAOYSA-N
SMILES Cl[H].[H][C@@]12C[C@@]3([H])C[C@@]([H])(C1)CC(N)(C2)C3
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)
UNSPSC Code 41116107
NACRES NA.77

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)  Exclamation Mark (GHS07)
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  TSCA listed
HazardClass  IRRITANT
HS Code  29213000
Storage Class 8A - Combustible corrosive hazardous materials
Hazard Classifications Acute Tox. 4 Oral
Toxicity LD50 orally in mice, rats: 700, 1275 mg/kg (Vernier)
REACH Registrations Active
NFPA 704
1
3 0

1-Adamantanamine hydrochloride price More Price(93)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A1260 Amantadine hydrochloride 665-66-7 5g $72.7 2026-04-30 Buy
Sigma-Aldrich BP530 Amantadine hydrochloride British Pharmacopoeia (BP) Reference Standard 665-66-7 200MG $282 2026-04-30 Buy
Sigma-Aldrich A0363000 Amantadine hydrochloride European Pharmacopoeia (EP) Reference Standard 665-66-7 100 mg $175 2026-04-30 Buy
Sigma-Aldrich 8.20015 1-Adamantaneammonium chloride for synthesis 665-66-7 10g $72.3 2026-04-30 Buy
Sigma-Aldrich 1018505 Amantadine hydrochloride United States Pharmacopeia (USP) Reference Standard 665-66-7 200mg $435 2026-04-30 Buy
Product number Packaging Price Buy
A1260 5g $72.7 Buy
BP530 200MG $282 Buy
A0363000 100 mg $175 Buy
8.20015 10g $72.3 Buy
1018505 200mg $435 Buy

1-Adamantanamine hydrochloride Chemical Properties, Uses, Production

Chemical Properties

Crystalline Solid

Originator

Symmetrel,DuPont (Endo),US,1966

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.

Uses

antiviral, antiparkinsonian; treatment of drug-induced extrapyrimidal reactions

Uses

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

Uses

NMDA-receptor antagonist. Antiviral; antiparkinsonian

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.

storage

Room temperature

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.]

References

[1] Synthetic Communications, 2015, vol. 45, # 22, p. 2601 - 2607
[2] Patent: WO2007/96124, 2007, A1. Location in patent: Page/Page column 15-16
[3] Russian Journal of Organic Chemistry, 2015, vol. 51, # 12, p. 1703 - 1709
[4] Zh. Org. Khim., 2015, vol. 51, # 12, p. 1737 - 1743,7

1-Adamantanamine hydrochloride synthesis

768-94-5
665-66-7
Synthesis of 1-Adamantanamine hydrochloride from Amantadine

1-Adamantanamine hydrochloride Preparation Products And Raw materials

Raw materials

Aluminium-nickel Amantadine Dicyclopentadiene Sodium sulfite Chlorine
Urea Aluminum chloride Hydrochloric acid Hydrogen Bromine
Sodium hydroxide Hydrogen cyanide Adamantane 2-Adamantanamine hydrochloride

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Preparation Products

1-Adamantanamine hydrochloride Suppliers

Global Suppliers ( 698)
Supplier Tel Email Country ProdList Advantage
Jinan Shengbang Biotechnology Co., Ltd. 13685312009 418162321@qq.com China 60 58
Sichuan Zhongbang Pharma CO.，LTD 0830-0830-2585019 13679670161 sales2@zhongbangst.com China 105 69
TIANJIN MINXIANG BIOMEDICAL INC. 13313219033 tjmx@mxpharm.com China 39 58
Huzhou Chenxi Environmental Protection Technology Co., Ltd. 16762203950 16762203950 3775386035@qq.com China 102 58
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 4006356688 18621169109 market03@meryer.com China 40202 62
INTATRADE GmbH +49 3493/605464 sales@intatrade.de Germany 3563 66
future industrial shanghai co., ltd 400-0066400 13621662912 sales@jonln.com China 1989 65
Alfa Aesar 400-6106006 saleschina@alfa-asia.com China 30103 84
TCI (Shanghai) Development Co., Ltd. 021-67121386 Sales-CN@TCIchemicals.com China 24512 81
Supplier Advantage
Jinan Shengbang Biotechnology Co., Ltd. 58
Sichuan Zhongbang Pharma CO.，LTD 69
TIANJIN MINXIANG BIOMEDICAL INC. 58
Huzhou Chenxi Environmental Protection Technology Co., Ltd. 58
J & K SCIENTIFIC LTD. 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 62
INTATRADE GmbH 66
future industrial shanghai co., ltd 65
Alfa Aesar 84
TCI (Shanghai) Development Co., Ltd. 81

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View Latest Price from 1-Adamantanamine hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
1-Adamantanamine hydrochloride pictures 2026-09-18 1-Adamantanamine hydrochloride
665-66-7
 $30.00-50.00 1kg 99% 5000 HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
1-Adamantanamine hydrochloride pictures 2026-09-18 1-Adamantanamine hydrochloride
665-66-7
 1KG 98.5%min 500kg WUHAN FORTUNA CHEMICAL CO., LTD
1-Adamantanamine hydrochloride pictures 2026-09-17 1-Adamantanamine hydrochloride
665-66-7
 0.99 RongNa Biotechnology Co.,Ltd

1-Adamantanamine hydrochloride Spectrum

1-Adamantanamine hydrochloride(665-66-7)MS1-Adamantanamine hydrochloride(665-66-7)1HNMR1-Adamantanamine hydrochloride(665-66-7)13CNMR1-Adamantanamine hydrochloride(665-66-7)IR11-Adamantanamine hydrochloride(665-66-7)IR21-Adamantanamine hydrochloride(665-66-7)Raman

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