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; |
amantadine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 10h; Heating; | 334 mg |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: nitric acid / 0.5 h / 25 - 30 °C 2: acetic acid / 0.5 h / 125 °C 3: acetic acid; nitric acid / water / 125 °C 4: sodium hydroxide / water 5: hydrogenchloride / diethyl ether View Scheme | |
Multi-step reaction with 2 steps 1.1: Nitrogen dioxide; ozone / 0.5 h / -78 - 30 °C 2.1: iron(III) chloride hexahydrate; hydrazine hydrate / ethanol; diethyl ether / 40 °C / Inert atmosphere 2.2: 0.5 h / 70 °C View Scheme |
1-nitroxyadamantane
amantadine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: acetic acid / 0.5 h / 125 °C 2: acetic acid; nitric acid / water / 125 °C 3: sodium hydroxide / water 4: hydrogenchloride / diethyl ether View Scheme |
1-(carbamoylamino)adamantne
amantadine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid; nitric acid / water / 125 °C 2: sodium hydroxide / water 3: hydrogenchloride / diethyl ether View Scheme | |
With hydrogenchloride; pyrographite In water at 70℃; for 1h; pH=3 - 4; Industrial scale; | 6.4 kg |
amantadine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water 2: hydrogenchloride / diethyl ether View Scheme |
Conditions | Yield |
---|---|
Stage #1: 1-acetyladamantane With tetrabutylammomium bromide; sodium hydroxide In water; ethylene glycol at 40 - 190℃; for 12h; Autoclave; Stage #2: With hydrogenchloride In water; ethylene glycol pH=4; |
adamantane
A
amantadine hydrochloride
B
adamantan-2-amine hydrochloride
Conditions | Yield |
---|---|
Stage #1: adamantane With methanol; cerium(III) chloride; di-tert-butyl-diazodicarboxylate; tetrabutyl-ammonium chloride In acetonitrile at 20℃; for 10h; Irradiation; Inert atmosphere; Sealed tube; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Reagent/catalyst; Further stages; |
Trimethyl orthoacetate
amantadine hydrochloride
N-(1-adamantyl)acetamide
Conditions | Yield |
---|---|
In methanol at 135℃; for 0.25h; Microwave irradiation; | 100% |
2,3,4-trifluorophenyl isocyanate
amantadine hydrochloride
1-(adamantan-1-yl)-3-(2,3,4-trifluorophenyl)urea
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; Inert atmosphere; | 100% |
2,2'-dithiodibenzoic acid dichloride
amantadine hydrochloride
N,N'-bis(1-adamantyl)-2,2'-dithiodibenzamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 5.5h; | 98% |
With triethylamine In dichloromethane at -15℃; for 0.25h; |
amantadine hydrochloride
alpha cyclodextrin
poly(ethylene glycol) 3500, bis[N-(1-adamantyl)aminocarbonyl]-terminated, inclusion complex with α-cyclodextrin, prepared with 1-adamantylamine and proton sponge
Conditions | Yield |
---|---|
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 4℃; | 95% |
Benzyl isothiocyanate
amantadine hydrochloride
1-(adamantane-2-yl)-3-benzylthiourea
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 80℃; for 8h; | 95% |
Conditions | Yield |
---|---|
With sodium carbonate In ethanol for 15h; Heating; | 94% |
Conditions | Yield |
---|---|
With sodium chloride; sodium hydroxide In water | 94% |
With sodium hydroxide In water | |
With sodium hydroxide In dichloromethane; water |
4-((3-formyl-4-hydroxyphenyl)diazenyl)benzenesulfonamide
amantadine hydrochloride
Conditions | Yield |
---|---|
With acetic acid Reflux; | 94% |
2-hydroxy-5-(p-chlorophenylazo)benzaldehyde
amantadine hydrochloride
Conditions | Yield |
---|---|
With acetic acid Reflux; | 94% |
2,4-Dinitrofluorobenzene
amantadine hydrochloride
N-(2,4-dinitrophenyl)adamantan-1-amine
Conditions | Yield |
---|---|
With triethylamine In acetonitrile for 48h; Reflux; Darkness; | 93% |
With potassium carbonate; triethylamine In acetonitrile for 48h; pH=8 - 9; Darkness; | 50% |
Boc-Glu-OBn
amantadine hydrochloride
N-(tert-butyloxycarbonyl)-L-glutamic acid α-benzyl ester γ-(1-adamantylamide)
Conditions | Yield |
---|---|
With diphenylphosphoranyl azide; diethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 21h; | 92% |
amantadine hydrochloride
phenyl isothiocyanate
1-(adamantane-2-yl)-3-phenylthiourea
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 80℃; for 8h; | 92% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 80℃; for 8h; | 92% |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 10 - 15℃; | 90% |
With sulfuric acid; nitric acid at 0 - 10℃; for 2h; | 81% |
Stage #1: amantadine hydrochloride With sulfuric acid; nitric acid at 0 - 20℃; Inert atmosphere; Stage #2: With sodium hydroxide In water | 72% |
Conditions | Yield |
---|---|
With aq. HCl In water stirring mixture of adamantane deriv., vanadium compd., water and DMF for few sec. at room temp., adjusting pH to 3 by addn. of 0.1 M aqueous HCl; filtration, keeping in air at room temp. for 2 w, elem. anal.; | 90% |
amantadine hydrochloride
N,N'-di(tert-butylcarbamate)adamantylamino-D-histidine amide
Conditions | Yield |
---|---|
With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; trimethylamine In dichloromethane at 20℃; Cooling with ice; | 90% |
Conditions | Yield |
---|---|
In hydrogenchloride; methanol adamantan-1-aminium chloride, 18-crown-6 were dissolved in MeOH, CuCl2 was added followed by concd. aq. HCl; filtered, slow evapd. at room temp., elam. anal.; | 90% |
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 .
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View