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665-66-7

Basic Information
CAS No.: 665-66-7
Name: 1-Adamantanamine hydrochloride
Article Data: 22
Molecular Structure:
Molecular Structure of 665-66-7 (1-Adamantanamine hydrochloride)
Formula: C10H18ClN
Molecular Weight: 187.713
Synonyms: 1-Adamantanamine HCl;1-Adamantanamine,hydrochloride (8CI);Adamantanamine hydrochloride (6CI);Tricyclo[3.3.1.13,7]decan-1-amine, hydrochloride (9CI);1-Adamantaminehydrochloride;Adamantylamine hydrochloride;Adamin;Adamine;Amazolon;Aminoadamantane hydrochloride;EXP 105-1;Mantadan;Mantadine;Midantane;Symmetrel;Virasol;Virofral;Tricyclo[3.3.1.13,7]decan-1-amine,hydrochloride (1:1);
EINECS: 211-560-2
Density: 1.067g/cm3
Melting Point: >300 °C(lit.)
Boiling Point: 1-Adamantanamine hydrochloride
Flash Point: 96 °C
Solubility: Soluble in water
Appearance: Crystalline solid
Hazard Symbols: IrritantXi
Risk Codes: 22-40-20/21/22
Safety: 22-36/37-36
PSA: 26.02000
LogP: 3.41620
Synthetic route
768-94-5

1-Adamantanamine

665-66-7

amantadine hydrochloride

Conditions
ConditionsYield
With hydroxylamine hydrochloride In ethanol for 2h; Reflux;100%
With hydrogenchloride In water; toluene at 0 - 20℃; for 1h; Product distribution / selectivity;
With hydrogenchloride In diethyl ether
24886-73-5

1-Azidoadamantane

665-66-7

amantadine hydrochloride

Conditions
ConditionsYield
With propan-1-ol; 2,2'-azobis(isobutyronitrile); phenylsilane; bis(tri-n-butyltin)oxide In benzene Reduction; Heating;99%
17341-91-2

2,2,2-trichloroethyl (adamantan-1-yl)carbamate

665-66-7

amantadine hydrochloride

Conditions
ConditionsYield
Stage #1: 2,2,2-trichloroethyl 1-adamantylcarbamate With acetic acid; zinc
Stage #2: With acetyl chloride In methanol Heating;
99%
880-52-4

N-(1-adamantyl)acetamide

665-66-7

amantadine hydrochloride

Conditions
ConditionsYield
Stage #1: N-(1-adamantyl)acetamide With sodium heptadecanoic acid; β‐cyclodextrin; sodium hydroxide In ethanol; water for 20h; Reflux;
Stage #2: With hydrogenchloride In water at 70℃;
96.5%
Stage #1: N-(1-adamantyl)acetamide With propylene glycol; potassium hydroxide In water at 125 - 130℃; for 8h; Green chemistry;
Stage #2: With hydrogenchloride In dichloromethane; water at 55 - 60℃; for 1h; Temperature; Time; Green chemistry;
82%
Stage #1: N-(1-adamantyl)acetamide With methanol; water; sodium hydroxide at 145℃; for 8h; Autoclave;
Stage #2: With hydrogenchloride In dichloromethane; water at 50℃; for 0.5h; Autoclave;
82.2%
3405-48-9

N-(1-adamantyl)formamide

665-66-7

amantadine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 85 - 90℃; for 1h;93%
7575-82-8

1-nitroadamantane

665-66-7

amantadine hydrochloride

Conditions
ConditionsYield
Stage #1: 1-nitroadamantane With iron(III) chloride hexahydrate; hydrazine hydrate In diethyl ether; ethanol at 40℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 70℃; for 0.5h;
89.5%
Stage #1: 1-nitroadamantane With C36H56Cl3CrN2O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Schlenk technique;
Stage #2: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate at 20℃;
83%
57680-77-0

adamantylmagnesium bromide

665-66-7

amantadine hydrochloride

Conditions
ConditionsYield
Stage #1: adamantylmagnesium bromide With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(I) cyanide*lithium chloride; 4,4'-bis(4-trifluoromethyl)benzophenone O-methylsulfonyloxime In tetrahydrofuran at 0℃; for 1h; Substitution;
Stage #2: With hydrogenchloride In water; acetone at 25℃; for 0.5h; Hydrolysis;
82%
Multi-step reaction with 2 steps
1: chlorobenzene; diethyl ether / 0.5 h / 0 °C
2: 334 mg / aq. HCl / ethanol / 10 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: CuCN*2LiCl / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / 0 °C
2: aq. HCl
View Scheme
768-90-1

1-Adamantyl bromide

665-66-7

amantadine hydrochloride

Conditions
ConditionsYield
Stage #1: 1-Adamantyl bromide With urea at 180 - 240℃;
Stage #2: With hydrogenchloride In water Temperature;
49.7%
24375-06-2

1-(Chloroamino)adamantane

A

24375-05-1

N,N-dichloro-adamantan-1-amine

B

665-66-7

amantadine hydrochloride

Conditions
ConditionsYield
silica gel In methanol; dichloromethane disproportionation; Yields of byproduct given;

Adamantan-1-yl-[bis-(4-trifluoromethyl-phenyl)-methylene]-amine

665-66-7

amantadine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride Yield given;
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Chemistry

Molecular Structure:
Molecular Formula: C10H18ClN
Molecular Weight: 187.71g/mol
CAS NO: 665-66-7
Mol File: 665-66-7.mol 
EINECS: 211-560-2 
H bond acceptors: 1
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 3.24 Å2
Melting Point: >300 °C(lit.)
Boiling point: 225.7 °C at 760 mmHg
Flash Point: 96 °C
Water Solubility: 50 mg/mL
Sensitive: Hygroscopic
Enthalpy of Vaporization: 46.22 kJ/mol
Vapour Pressure: 0.0852 mmHg at 25°C 
Appearance: Crystalline Solid
IUPAC Name: Adamantan-1-amine hydrochloride
InChI : InChI=1/C10H17N.ClH/c11-10-4-7-1-8(5-10)3-9(2-7)6-10;/h7-9H,1-6,11H2;1H     
Smiles: Cl.C1C2CC3CC1CC(C3)(C2)N
Product Categories of Amantadine hydrochloride (CAS NO.665-66-7): Adamantane derivatives; chiral; Adamantanes; Intermediates & Fine Chemicals; Pharmaceuticals; API's; Dopamine receptor

Uses

 Amantadine hydrochloride (CAS NO.665-66-7) is used as NMDA-receptor antagonist.

Toxicity Data With Reference

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.

Safety Profile

Safety Information of Amantadine hydrochloride (CAS NO.665-66-7):
Hazard Codes: XnHarmful
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 

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 .