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| CAS No.: | 665-66-7 |
|---|---|
| Name: | 1-Adamantanamine hydrochloride |
| Article Data: | 22 |
| Molecular Structure: | |
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|
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| 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: |
 Xi
|
| Risk Codes: | 22-40-20/21/22 |
| Safety: | 22-36/37-36 |
| PSA: | 26.02000 |
| LogP: | 3.41620 |
| Conditions | Yield |
|---|---|
| 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 |
1-Azidoadamantane
amantadine hydrochloride
| Conditions | Yield |
|---|---|
| With propan-1-ol; 2,2'-azobis(isobutyronitrile); phenylsilane; bis(tri-n-butyltin)oxide In benzene Reduction; Heating; | 99% |
2,2,2-trichloroethyl (adamantan-1-yl)carbamate
amantadine hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: 2,2,2-trichloroethyl 1-adamantylcarbamate With acetic acid; zinc Stage #2: With acetyl chloride In methanol Heating; | 99% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| With hydrogenchloride In ethanol; water at 85 - 90℃; for 1h; | 93% |
| Conditions | Yield |
|---|---|
| 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% |
adamantylmagnesium bromide
amantadine hydrochloride
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| Stage #1: 1-Adamantyl bromide With urea at 180 - 240℃; Stage #2: With hydrogenchloride In water Temperature; | 49.7% |
1-(Chloroamino)adamantane
A
N,N-dichloro-adamantan-1-amine
B
amantadine hydrochloride
| Conditions | Yield |
|---|---|
| silica gel In methanol; dichloromethane disproportionation; Yields of byproduct given; |
amantadine hydrochloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride Yield given; |
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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
Amantadine hydrochloride (CAS NO.665-66-7) is used as NMDA-receptor antagonist.
| 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 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
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 .
