1-Adamantanamine hydrochloride structure

3D Mol Similar

1-Adamantanamine hydrochloride

: Iupac Name：adamantan-1-amine;hydrochloride; CAS No.: 665-66-7; Molecular Weight：187.711; Modify Date.: 2024-03-31 06:40; Introduction: antiviral, antiparkinsonian; treatment of drug-induced extrapyrimidal reactions View more+

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1. Names and Identifiers

: 1.1 Name; 1-Adamantanamine hydrochloride; 1.2 Synonyms; (1s,3R,5S)-1-Adamantanamine hydrochloride (1:1) 1-adamantamine hydrochloride 1-Adamantanamine Hydrochleride 1-Adamantanaminehydrochloride 1-adamantane amine hydrochloride 1-adamantylamine hydrochloride 1-aminoadamantane hydrochloride 1-Aminoadamantane Hydrochloride Amantadine Hydrochloride 211-560-2 adamantanamine hydrochloride Adekin Amantadine (hydrochloride) Amantadine HCl Amantadine hydrochloride Amantadine Hydrochloride (200 mg) Amantadine hydrochloride,1-Adamantanamine hydrochloride, 1-Adamantylamine hydrochloride, 1-Aminoadamantane hydrochloride Amazolon EINECS 211-560-2 exp105-1 Lysovir Mantadan Mantadix MFCD00074723 Midantan Tricyclo[3.3.1.13,7]decan-1-amine, (3R,5S)-, hydrochloride (1:1) virasol Virofral; View all

1.3 CAS No.: 665-66-7

1.4 CID: 64150

1.5 EINECS(EC#): 211-560-2

1.6 Molecular Formula: C10H18ClN (isomer)

1.7 Inchi: InChI=1S/C10H17N.ClH/c11-10-4-7-1-8(5-10)3-9(2-7)6-10;/h7-9H,1-6,11H2;1H

1.8 InChIkey: WOLHOYHSEKDWQH-UHFFFAOYSA-N

1.9 Canonical Smiles: C1C2CC3CC1CC(C2)(C3)N.Cl

1.10 Isomers Smiles: C1C2CC3CC1CC(C2)(C3)N.Cl

2. Properties

2.1 Density: 1.067

2.1 Melting point: 300℃

2.1 Boiling point: 225.7 °C at 760 mmHg

2.1 Refractive index: 1.558

2.1 Flash Point: 96 °C

2.1 Precise Quality: 187.11300

2.1 PSA: 26.02000

2.1 logP: 3.41620

2.1 Solubility: H2O: 50?mg/mL

2.2 AnalyticLaboratory Methods: Analyte: amantadine;; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards /amantadine hydrochloride;/

2.3 Appearance: Crystalline Solid

2.4 Storage: Ambient temperatures.

2.5 Chemical Properties: Crystalline Solid

2.6 Color/Form: HEXAKISTETRAHEDRAL CRYSTALS BY SUBLIMATION

2.7 pKa: pKa = 10.45 (est)

2.8 Water Solubility: soluble

2.9 Spectral Properties: IR: 7570 (Coblentz Society Infrared Spectral Database)
NMR: 15203 (Sadtler Research Laboratories Spectral Collection)
MASS: 90068 (NIST/EPA/MSDC Mass Spectral Database, 1990 version

2.10 StorageTemp: Store in a cool, dry place. Store in a tightly closed container.

3. Use and Manufacturing

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

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 142 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (99.3%): Harmful if swallowed [Warning Acute toxicity, oral]
H314 (75.35%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H318 (74.65%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H336 (27.46%): May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure; Narcotic effects]
H361 (77.46%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H412 (75.35%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P363, P403+P233, P405, and P501; View all

3.3 Methods of Manufacturing: Amantadine; is brominated to 1-bromo compound, which is then reacted with acetonitrile; in presence of sulfuric acid; to produce n-(1-adamantanyl)acetamide. Alkaline hydrolysis liberates amantadine;, which is reacted with hydrogen chloride; in suitable solvent to yield official salt. /amantadine hydrochloride;/

3.4 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.] 1-Adamantanamine hydrochloride Preparation Products And Raw materials Raw materials

3.5 Usage: antiviral, antiparkinsonian; treatment of drug-induced extrapyrimidal reactions

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22

4.1 Safety Statements: 22-36/37-36

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl amantadine hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Amantadine hydrochloride/

4.2 Octanol/Water Partition Coefficient: log Kow = 2.44

4.3 Hazard Class: IRRITANT

4.3 Hazard Declaration: H302

4.3 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.4 RIDADR: UN 1759 8 / PGII

4.4 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.

4.5 Caution Statement: P301 + P312 + P330

4.5 Formulations/Preparations: Oral: Capsules, liquid-filled Tablets: 100 mg (available by nonpropriety name), 100 mg, Symmetrel, (Endo); Solution: 50 mg/5 mL, Symmetrel Syrup ( with parabens), (Endo).
Trade Names.Hydrochloride: Amazolon (Sawai), Mantadine (Du Pont), Mantadix (Du Pont, Rh?ne-Poulenc), Symmetrel (Ciba-Geigy), Virofral (Ferrosan). Sulfate: Contenton (SKD), PK-Merz (Merz).
administered PO, intranasal, SC, IP, or aerosol routes.

4.6 WGK Germany: 3

4.6 RTECS: AU4375000

4.6 Safety: Safety Information of Amantadine hydrochloride (CAS NO.665-66-7):
Hazard Codes: Xn
Risk Statements: 22-40-20/21/22
20:?Harmful by inhalation?
21:?Harmful in contact with skin?
22:?Harmful if swallowed?
40:?Limited evidence of a carcinogenic effect?
Safety Statements: 22-36/37-36
22:?Do not breathe dust?
36:?Wear suitable protective clothing??
37:?Wear suitable gloves?

4.7 Sensitive: Hygroscopic

4.8 Specification: ?The chemical synonyms of?Amantadine hydrochloride (CAS NO.665-66-7): 1-Adamantanamine hydrochloride ; AI3-52211 ; Adamantanamine hydrochloride ; Adamantine hydrochloride ; Amantadine HCl ; Amantan ; Amazolon ; Aminoadamantane hydrochloride ; EXP 105-1 ; GP 38026 ; Influenol ; Mydantane ; NSC 83653 ; Symmetrel ; Trivaline ; UNII-M6Q1EO9TD0 ; Tricyclo(3.3.1.1(sup 3,7))decan-1-amine, hydrochloride (9CI) ; Tricyclo(3.3.1.13,7)decan-1-amine, hydrochloride .

4.9 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	intravenous	37mg/kg (37mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Toxicology and Applied Pharmacology. Vol. 15, Pg. 642, 1969.
guinea pig	LD50	oral	360mg/kg (360mg/kg)	BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Toxicology and Applied Pharmacology. Vol. 15, Pg. 642, 1969.
man	LDLo	oral	28571ug/kg (28.571mg/kg)	BEHAVIORAL: TOXIC PSYCHOSIS LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA BLOOD: HEMORRHAGE	American Journal of Psychiatry. Vol. 145, Pg. 267, 1988.
man	LDLo	oral	286mg/kg (286mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: EXCITEMENT BEHAVIORAL: TOXIC PSYCHOSIS	American Journal of Psychiatry. Vol. 145, Pg. 267, 1988.
man	TDLo	oral	13mg/kg/5D-I (13mg/kg)	BEHAVIORAL: EUPHORIA BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"	American Journal of Psychiatry. Vol. 143, Pg. 1170, 1985.
man	TDLo	oral	24mg/kg/1D-I (24mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: EXCITEMENT	Annals of Emergency Medicine. Vol. 19, Pg. 668, 1990.
mouse	LD50	intraperitoneal	198mg/kg (198mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 164, 1988.
mouse	LD50	intravenous	95mg/kg (95mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 164, 1988.
mouse	LD50	oral	700mg/kg (700mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Toxicology and Applied Pharmacology. Vol. 15, Pg. 642, 1969.
mouse	LD50	subcutaneous	290mg/kg (290mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 164, 1988.
rat	LD50	intraperitoneal	150mg/kg (150mg/kg)	BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Toxicology and Applied Pharmacology. Vol. 15, Pg. 642, 1969.
rat	LD50	intravenous	90mg/kg (90mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 164, 1988.
rat	LD50	oral	800mg/kg (800mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 164, 1988.
rat	LD50	subcutaneous	500mg/kg (500mg/kg)	?	Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 13, Pg. 1269, 1971.
women	LDLo	oral	50mg/kg (50mg/kg)	BEHAVIORAL: COMA CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP CARDIAC: PULSE RATE	American Journal of Medicine. Vol. 77, Pg. 388, 1984.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin corrosion, Category 1B

Serious eye damage, Category 1

Reproductive toxicity, Category 2

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 3

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H314 Causes severe skin burns and eye damage H361 Suspected of damaging fertility or the unborn child H402 Harmful to aquatic life H412 Harmful to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P280 Wear protective gloves/protective clothing/eye protection/face protection. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 90 MHz in CDCl3

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Raman : 4880 A,200 M,powder

Mass

7. Synthesis Route

665-66-7Total: 6 Synthesis Route

768-94-5 213 Suppliers

665-66-7 364 Suppliers

Literatures:
WO2007/96124 A1, ; Page/Page column 15-16 ;
Yield: null

880-52-4 104 Suppliers

665-66-7 364 Suppliers

Literatures:
Organic Letters, , vol. 11, # 2 p. 433 - 436
Yield: null

24886-73-5 1 Suppliers

665-66-7 364 Suppliers

Literatures:
Hays, David S.; Fu, Gregory C. Journal of Organic Chemistry, 1998 , vol. 63, # 9 p. 2796 - 2797
Yield: ~97%

View all

8. Precursor and Product

precursor:

768-94-5

17341-91-2

57680-77-0

24886-73-5

24375-06-2

880-52-4

product :

5592-71-2

3716-67-4

50606-99-0

3717-60-0

768-94-5

5689-59-8

32901-14-7

3716-66-3

915923-76-1

702-82-9

3717-40-6

56916-85-9

25444-82-0

13072-69-0

4411-25-0

22110-53-8

2387-23-7

274901-16-5

915922-22-4

458529-20-9

View all

9. Other Information

9.0 Usage: 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.

10. Computational chemical data

Molecular Weight: 187.711g/mol
Molecular Formula: C₁₀H₁₈ClN
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 187.1127773
Monoisotopic Mass: 187.1127773
Complexity: 144
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 26
Heavy Atom Count: 12
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceByAAAEAAAAAAAAAAAAAAAAAAAAAAAwYMGAAAAAAAAAAAAAHAAQAAAADYiBAAAAAABAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAIAgAAAAAAAEAAAAAEQgMAOAAAAAAAAAAAAAASAAAAAAAAAAAAAAA==

11. Question & Answer

What is the background technology of 1-Adamantanamine hydrochloride and how is it prepared? Mar 08 2023
Background Technology 1-Adamantanamine hydrochloride is the first approved antiviral drug in the United States. It was discovered by Davis in 1964 and subsequently included in the British Pharmacopoei..
What should be noted in the instructions for 1-Adamantanamine hydrochloride? Nov 17 2022
The medicinal value of 1-Adamantanamine hydrochloride is quite diverse. Correct usage is crucial for preventing viral infections and effectively inhibiting harmful bacteria growth, making it highly ef..
How to Transport and Store 1-Adamantanamine Hydrochloride? Sep 14 2022
1-Adamantanamine hydrochloride, an organic compound, is widely used in medical research for the prevention and treatment of various strains of influenza A virus. It has shown ideal effectiveness and h..
Can 1-Adamantanamine hydrochloride be taken when having a cold? Sep 01 2022
Colds are a common illness among humans, caused by viral infections. When cold viruses enter the body, the immune system produces antibodies to fight against them. However, these antibodies do not sta..

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