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Name	Amantadine	EINECS	212-201-2
CAS No.	768-94-5	Density	1.067 g/cm³
PSA	26.02000	LogP	2.61420
Solubility	Soluble in organic solvents,insoluble in water.	Melting Point	206-208 °C(lit.)
Formula	C₁₀H₁₇N	Boiling Point	225.692 °C at 760 mmHg
Molecular Weight	151.252	Flash Point	95.974 °C
Transport Information	N/A	Appearance	White to cream powder
Safety	26-36	Risk Codes	22-36/37/38
Molecular Structure		Hazard Symbols	Xn, Xi
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;	Article Data	97

Amantadine Synthetic route

: 7575-82-8
1-nitroadamantane

: 768-94-5
1-Adamantanamine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With boric acid In ethanol Heating;	96%

: 768-90-1
1-Adamantyl bromide

: 768-94-5
1-Adamantanamine

Conditions

Conditions	Yield
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

Conditions	Yield
With sodium chloride; sodium hydroxide In water	94%
With sodium hydroxide In water
With sodium hydroxide In dichloromethane; water

: 880-52-4
N-(1-adamantyl)acetamide

: 768-94-5
1-Adamantanamine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With indium; ammonium chloride In ethanol for 6h; Heating;	91%

Amantadine Chemical Properties

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

Amantadine 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.

Amantadine Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Amantadine Safety Profile

Hazard Codes : Xn Harmful ,Xi Irritant
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 NO_x. Used as an antiviral agent.

Amantadine 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 .

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