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Basic Information
CAS No.: 768-94-5
Name: Amantadine
Article Data: 97
Molecular Structure:
Molecular Structure of 768-94-5 (Amantadine)
Formula: C10H17N
Molecular Weight: 151.252
Synonyms: 1-Adamantanamine(6CI,8CI);(Adamantan-1-yl)amine;1-Adamantamine;1-Adamantylamine;1-Amantadine;1-Aminoadamantane;Adamantamine;Adamantanamine;Adamantylamine;NSC 341865;Tricyclo[3.3.1.13,7]decane-1-amine;
EINECS: 212-201-2
Density: 1.067 g/cm3
Melting Point: 206-208 °C(lit.)
Boiling Point: 225.692 °C at 760 mmHg
Flash Point: 95.974 °C
Solubility: Soluble in organic solvents,insoluble in water.
Appearance: White to cream powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36/37/38
Safety: 26-36
PSA: 26.02000
LogP: 2.61420
Synthetic route
7575-82-8

1-nitroadamantane

768-94-5

1-Adamantanamine

Conditions
ConditionsYield
With sodium dithionite; potassium carbonate; 1,1′-dioctyl-4,4′-bipyridinium In water; acetonitrile at 35℃; for 24h;98%
With hydrazine hydrate; ammonia In ethanol Reagent/catalyst; Solvent;
28309-44-6

(3r,5r,7r)-N-hydroxyadamantane-1-carboxamide

768-94-5

1-Adamantanamine

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 3h; Lossen Rearrangement;98%
Stage #1: adamantane-1-carboxylic acid hydroxyamide With acetic anhydride; potassium carbonate In dimethyl sulfoxide at 50℃; for 6h; Lossen Rearrangement;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 0℃;
67%
Stage #1: adamantane-1-carboxylic acid hydroxyamide With potassium carbonate In dimethyl sulfoxide at 90℃; for 3h; Lossen Rearrangement;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; for 1h;
141903-89-1

Adamantan-1-yl-[2,2,2-trifluoro-1-phenyl-eth-(Z)-ylidene]-amine

A

434-45-7

1,1,1-trifluoroacetophenone

B

768-94-5

1-Adamantanamine

Conditions
ConditionsYield
With water; boric acid In ethanol at 80℃; for 8h;A n/a
B 96%
141903-89-1

Adamantan-1-yl-[2,2,2-trifluoro-1-phenyl-eth-(Z)-ylidene]-amine

768-94-5

1-Adamantanamine

Conditions
ConditionsYield
With boric acid In ethanol Heating;96%
768-90-1

1-Adamantyl bromide

768-94-5

1-Adamantanamine

Conditions
ConditionsYield
With ammonium bicarbonate at 135℃; for 6h; Concentration; Temperature; Autoclave;94.7%
Stage #1: 1-Adamantyl bromide With magnesium Inert atmosphere;
Stage #2: With 3,3’-di-tert-butyl oxaziridine In diethyl ether at 20℃; for 6h; Inert atmosphere;
55%
With urea
With urea at 170 - 190℃;
665-66-7

amantadine hydrochloride

768-94-5

1-Adamantanamine

Conditions
ConditionsYield
With sodium chloride; sodium hydroxide In water94%
With sodium hydroxide In water
With sodium hydroxide In dichloromethane; water
880-52-4

N-(1-adamantyl)acetamide

768-94-5

1-Adamantanamine

Conditions
ConditionsYield
With ammonium bromide; ethylenediamine at 100℃; for 5h; Microwave irradiation;93%
With ammonium bromide; ethylenediamine at 90℃; for 10h; Microwave irradiation; Inert atmosphere; neat (no solvent);92%
With sodium hydroxide In 1,2-dimethoxyethane at 135℃; for 12h; Solvent; Temperature; Time;90%
24886-73-5

1-Azidoadamantane

768-94-5

1-Adamantanamine

Conditions
ConditionsYield
With 1,3-diadamantane-4,5-dihydroimidazole chloride; potassium tert-butylate; bis(pinacol)diborane; copper(l) chloride In toluene at 25℃; for 4h; Schlenk technique; Inert atmosphere;92%
With PEG3400-PPh3 conjugate In dichloromethane for 4.5h; Ambient temperature;91%
With hydrazine hydrate; palladium dihydroxide; pyrographite In methanol for 2h; Heating;88%
56432-99-6

1-tosylaminoadamantane

768-94-5

1-Adamantanamine

Conditions
ConditionsYield
With propylamine; lithium In ethylenediamine at 20 - 42℃; for 2h; Reduction;91%
17341-91-2

2,2,2-trichloroethyl ((3s,5s,7s)-adamantan-1-yl)carbamate

768-94-5

1-Adamantanamine

Conditions
ConditionsYield
With indium; ammonium chloride In ethanol for 6h; Heating;91%
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    Molecular Formula C10H17N Molecular Weight 151.25 CAS Registry Number 768-94-5 EINECS 212-201-2 Items Specification Appearance White crystal or crystalline powder, odo(u)rless and bitter. … Appearance:white crystal powder Storage:dry and coo

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Chemistry


IUPAC Name: Adamantan-1-amine 
Molecular Formula: C10H17N
Formula Weight: 151.25
Melting point: 206-208 °C (lit.)
Index of Refraction: 1.557 
Flash Point: 96 °C 
Boiling Point: 225.7 °C  at 760 mmHg
Density: 1.066 g/cm3 
Index of Refraction: 1.557 
Molar Refractivity: 45.67 cm3 
Molar Volume: 141.7 cm3
Surface Tension:  46.7 dyne/cm 
Enthalpy of Vaporization: 46.22 kJ/mol 
Vapour Pressure: 0.0852 mmHg at 25°C
Appearance: Off-white to pale-yellow powder
XLogP3-AA: 2.4
H-Bond Donor: 1
H-Bond Acceptor: 1
Canonical SMILES: C1C2CC3CC1CC(C2)(C3)N
InChI: InChI=1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2  
InChIKey: DKNWSYNQZKUICI-UHFFFAOYSA-N
Product Categories of Amantadine (CAS NO.768-94-5): Adamantane derivatives

Toxicity Data With Reference

1.    

dnd-esc 10 µmol/L

    MUREAV    Mutation Research. 89 (1981),95.
2.    

orl-mus LD50:900 mg/kg

    DRFUD4    Drugs of the Future. 5 (1980),557.
3.    

ipr-mus LD50:245 mg/kg

    DRFUD4    Drugs of the Future. 5 (1980),557.

Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Safety Profile

Hazard Codes : XnHarmful,XiIrritant
Risk Statements : 22-36/37/38 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements : 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany : 3
RTECS of Amantadine (CAS NO.768-94-5): YD1925000
Poison by intraperitoneal route. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. Used as an antiviral agent.

Specification

 Amantadine , its CAS NO. is 768-94-5, the synonyms are 1-Adamantanamine ; 1-Adamantylamine ; 1-Aminoadamantane ; 1-Aminotricyclo(3.3.1.1(sup 3,7))decane ; Adamantanamine ; Adamantylamine ; Amantadinum ; Aminoadamantane ; Tricyclo(3.3.1.1(3,7))-decan-1-amine ; Tricyclo(3.3.1.1(sup 3.7))decan-1-amine .