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| CAS No.: | 768-94-5 |
|---|---|
| Name: | Amantadine |
| Molecular Structure: | |
|
|
|
| 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: |
 Xn,  Xi
|
| Risk Codes: | 22-36/37/38 |
| Safety: | 26-36 |
| PSA: | 26.02000 |
| LogP: | 2.61420 |
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| 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 | 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 | 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 | Yield |
|---|---|
| With boric acid In ethanol Heating; | 96% |
| 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℃; |
| Conditions | Yield |
|---|---|
| With sodium chloride; sodium hydroxide In water | 94% |
| With sodium hydroxide In water | |
| With sodium hydroxide In dichloromethane; water |
| 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 | 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 | 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 | Yield |
|---|---|
| With indium; ammonium chloride In ethanol for 6h; Heating; | 91% |
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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 : Xn
,Xi
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 .