3-isopropyl-5-<(nphthyloxy)methyl>oxazolidin-2-one
propranolol
Conditions | Yield |
---|---|
With potassium hydroxide In benzene for 24h; Heating; | 100% |
Conditions | Yield |
---|---|
With acetic acid In water at 20℃; for 8h; | 99% |
In water | 94% |
Stage #1: 3-(1-naphthyloxy)-1,2-epoxypropane With calcium chloride In acetonitrile Stage #2: isopropylamine In acetonitrile Further stages.; | 93% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In water at 20℃; for 24h; Inert atmosphere; Green chemistry; | 94% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium hydroxide In water at 0 - 100℃; for 5h; Reagent/catalyst; Solvent; | 90% |
Stage #1: α-naphthol; epichlorohydrin With potassium tert-butylate In dimethyl sulfoxide at 70℃; for 0.333333h; Williamson Ether Synthesis; Flow reactor; Stage #2: isopropylamine In dimethyl sulfoxide at 140℃; under 5250.53 Torr; for 0.333333h; Flow reactor; | 47 %Chromat. |
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene at 40℃; for 4h; Solvent; Temperature; | 88.9% |
3-(1-naphthyloxy)-1,2-epoxypropane
isopropylamine
A
N-Isopropyl-N,N-di-<3-(1-naphthoxy)-2-hydroxypropyl>amin
B
propranolol
Conditions | Yield |
---|---|
In toluene for 4h; | A 60% B n/a |
1-(3,4-Dihydro-naphthalen-1-yloxy)-3-isopropylamino-propan-2-ol
propranolol
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone | 59% |
Conditions | Yield |
---|---|
In tetrahydrofuran | A n/a B n/a C 35% |
1-(isopropylamino)-3-(naphthalen-1-yloxy)propan-2-yl acetate
propranolol
Conditions | Yield |
---|---|
at 37℃; Rate constant; plasma intestine and liver of rats; |
N'-tert-Butyl-N-[2-hydroxy-3-(naphthalen-1-yloxy)-propyl]-N-isopropyl-formamidine
propranolol
Conditions | Yield |
---|---|
With potassium hydroxide; water In methanol at 60℃; for 12h; Yield given; |
O-pivaloyl-1-(1-naphthyloxy)-3-isopropylaminopropan-2-ol hydrochloride
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
propranolol
Conditions | Yield |
---|---|
With phosphate buffer (μ = 0.15) In dimethyl sulfoxide at 37℃; Rate constant; var. pH; hydrolysis in buffers and enzymatic hydrolysis in blood plasma and liver homogenate, both taken from beagle dogs; |
1--N-isopropylamino>-3-(1-naphthyloxy)-2-propanol
A
carbon dioxide
B
acetaldehyde
C
acetic acid
D
propranolol
Conditions | Yield |
---|---|
With phosphate buffer; water at 37℃; Product distribution; pH 7.4, further reagent, half-lives; |
1-(isopropylamino)-3-(naphthalen-1-yloxy)propan-2-yl acetate
A
N-[2-hydroxy-3-(1-naphthalenyloxy)propyl]-N-(1-methylethyl)acetamide
B
propranolol
Conditions | Yield |
---|---|
With potassium hydroxide In water; acetone at 25℃; Rate constant; |
1-isopropyl-2-naphthalen-1-yloxymethyl-aziridine
propranolol
Conditions | Yield |
---|---|
With sulfuric acid |
di-tert-butyl dicarbonate
propranolol
rac-N-tert-Butoxycarbonyl-N-isopropyl-N-[2-hydroxy-3-(1-naphthyloxy)propyl]amine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 98.7% |
Conditions | Yield |
---|---|
for 48h; Ambient temperature; | 95% |
propranolol
Conditions | Yield |
---|---|
With thionyl chloride In ethanol at 0 - 10℃; for 3h; Temperature; Solvent; | 93.5% |
Conditions | Yield |
---|---|
Stage #1: propranolol With L-Tartaric acid In ethanol for 10h; Reflux; Stage #2: With sodium hydrogencarbonate In toluene at 25℃; for 0.333333h; Cooling with ice; | 88% |
Conditions | Yield |
---|---|
Stage #1: propranolol With sodium hydride In N,N-dimethyl-formamide at 35 - 40℃; for 0.5h; Stage #2: propyl bromide In N,N-dimethyl-formamide at 20℃; for 1h; | 86% |
Conditions | Yield |
---|---|
Stage #1: propranolol With sodium hydride In N,N-dimethyl-formamide at 35 - 40℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 1h; | 86% |
Conditions | Yield |
---|---|
Stage #1: propranolol With pyrographite In ethanol for 0.5h; Reflux; Stage #2: With hydrogenchloride at 4℃; pH=2; | 85.1% |
With hydrogenchloride In ethanol; water | 79.7% |
Conditions | Yield |
---|---|
In acetonitrile at 30℃; for 0.5h; pH=9.5; Temperature; | A 85.08% B 83.14% |
(E)-3-(3-phenoxyphenyl)acrylic acid
propranolol
Conditions | Yield |
---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 24h; | 79% |
propranolol
1-{[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ylsulfanyl]-isopropyl-amino}-3-(naphthalen-1-yloxy)-propan-2-ol
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide | 76% |
formic acid ethyl ester
propranolol
1-<<(1-methylethyl)-formyl>amino>-3-(1-naphthalenyloxy)-2-propanol
Conditions | Yield |
---|---|
for 48h; Heating; | 75% |
Conditions | Yield |
---|---|
With dmap at 60℃; for 12h; | 75% |
With dmap |
(Z)-ethyl 2-bromobut-2-enoate
propranolol
Conditions | Yield |
---|---|
In tetrahydrofuran; water | 75% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 0.5h; | 72% |
acrylonitrile
propranolol
A
3-((1-(isopropylamino)-3-(naphthalen-1-yloxy)propan-2-yl)oxy)propanenitrile
B
3-((2-hydroxy-3-((naphthalen-1-yloxy)propyl)isopropyl)amino)propanenitrile
Conditions | Yield |
---|---|
With n-butyllithium; copper(I) 2-hydroxy-3-methylbenzoate; 1,2-bis-(diphenylphosphino)ethane In hexane; N,N-dimethyl-formamide at 20℃; for 3h; Michael Addition; Inert atmosphere; chemoselective reaction; | A 63% B n/a |
methyl iodide
propranolol
1-(N-Isopropyl-N,N-dimethylamino)-3-(α-naphthoxy)propan-2-ol iodide
Conditions | Yield |
---|---|
With sodium hydroxide In isopropyl alcohol | 62% |
propranolol
1-<<(1-methylethyl)-formyl>amino>-3-(1-naphthalenyloxy)-2-propanol
Conditions | Yield |
---|---|
With water; malonic acid dimethyl ester In methanol at 45℃; for 52h; Reflux; | 62% |
3,4-dimethoxy-trans-cinnamic acid
propranolol
Conditions | Yield |
---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 24h; | 62% |
Conditions | Yield |
---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 24h; | 60% |
propranolol
Conditions | Yield |
---|---|
With 1H-imidazole In tetrahydrofuran at 100℃; for 2h; Microwave irradiation; Sealed tube; | 60% |
N-diphenoxymethylene benzamide
propranolol
Conditions | Yield |
---|---|
In dichloromethane for 5h; Ambient temperature; | 58% |
acetic anhydride
propranolol
N-[2-acetyloxy-3-(1-naphthalenyloxy)propyl]-N-(1-methylethyl)acetamide
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 4h; | 54% |
Molecular Structure of Inderal (CAS NO.525-66-6):
Molecular Formula: C16H21NO2
Molecular Weight: 259.34344
IUPAC Name: 1-(Isopropylamino)-3-(1-naphthyloxy)propan-2-ol
CAS: 525-66-6
EINECS: 208-378-0
SMILES: OC(CNC(C)C)COc2cccc1ccccc12
InChI: InChI=1/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3
InChIKey: AQHHHDLHHXJYJD-UHFFFAOYAS
Std.InChI: InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3
Std.InChIKey: AQHHHDLHHXJYJD-UHFFFAOYSA-N
Melting Point: 163-164℃
Boiling Point: 434.9℃ at 760mmHg
Flash Point: 216.8℃
Molar Volume: 237.1cm3
Density: 1.093g/cm3
Index of Refraction: 1.58
Molar Refractivity: 78.98cm3
Surface Tension: 42.6dyne/cm
Polarizability: 31.31 10-24cm3
Enthalpy of Vaporization: 72.84kJ/mol
Vapour Pressure: 2.48E-08mmHg at 25℃
Inderal (CAS NO.525-66-6) can be used for medication (vet).
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
child | LDLo | oral | 800ug/kg/12H (0.8mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA | British Medical Journal. Vol. 2, Pg. 254, 1978. |
child | TDLo | oral | 400mg/kg (400mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | Medical Journal of Australia. Vol. 1, Pg. 82, 1981. |
dog | LDLo | intraperitoneal | 40mg/kg (40mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Pharmazie. Vol. 31, Pg. 635, 1976. |
dog | LDLo | oral | 120mg/kg (120mg/kg) | SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE BEHAVIORAL: ATAXIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 69(4), Pg. 262P, 1973. |
guinea pig | LD50 | intravenous | 26mg/kg (26mg/kg) | Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 24, Pg. 103, 1972. | |
human | LDLo | intravenous | 71ug/kg (0.071mg/kg) | Lancet. Vol. 1, Pg. 165, 1967. | |
human | TDLo | oral | 2300ug/kg/D (2.3mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | British Medical Journal. Vol. 1, Pg. 1182, 1978. |
man | TDLo | oral | 8343mg/kg/4Y- (8343mg/kg) | ENDOCRINE: EVIDENCE OF THYROID HYPERFUNCTION | Archives of Internal Medicine. Vol. 143, Pg. 2193, 1983. |
man | TDLo | unreported | 22857ug/kg/40 (22.857mg/kg) | SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR | British Medical Journal. Vol. 289, Pg. 1490, 1984. |
mouse | LD50 | intraperitoneal | 42mg/kg (42mg/kg) | AUTONOMIC NERVOUS SYSTEM: BETA ADRENERGIC BLOCKAGE | Ain Shams Medical Journal. Vol. 30, Pg. 23, 1979. |
mouse | LD50 | intravenous | 24400ug/kg (24.4mg/kg) | United States Patent Document. Vol. #4013663, | |
mouse | LD50 | oral | 289mg/kg (289mg/kg) | AUTONOMIC NERVOUS SYSTEM: BETA ADRENERGIC BLOCKAGE | Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1831, 1980. |
mouse | LD50 | subcutaneous | 150mg/kg (150mg/kg) | Farmakologiya i Toksikologiya Vol. 44, Pg. 342, 1981. | |
rat | LD50 | intravenous | 23mg/kg (23mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA | Pharmazie. Vol. 31, Pg. 635, 1976. |
rat | LD50 | oral | 660mg/kg (660mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA | Pharmazie. Vol. 31, Pg. 635, 1976. |
women | LDLo | oral | 120mg/kg (120mg/kg) | Acta Pharmacologica et Toxicologica. Vol. 41, Pg. 190, 1977. | |
women | TDLo | oral | 3200ug/kg/2D- (3.2mg/kg) | ENDOCRINE: HYPOGLYCEMIA | Israel Journal of Medical Sciences. Vol. 18, Pg. 725, 1982. |
women | TDLo | oral | 708mg/kg/39W- (708mg/kg) | Annals of Pharmacotherpy. Vol. 27, Pg. 512, 1993. |
A deadly human poison by ingestion and intravenous routes. Poison experimentally by ingestion, intraperitoneal, intravenous, and subcutaneous routes. Human systemic effects by ingestion: cardiac arrhythmias, hallucinations, hypoglycemia, convulsions, and thyroid malfunction. Human reproductive and teratogenic effects by ingestion: extra embryonic structures, abnormal Apgar score in newborn, and abnormal growth statistics. Mutation data reported.
Inderal (CAS NO.525-66-6),which also can be called for 1-Isopropylamino-3-(1-naphthyloxy)propan-2-ol ; Propranolol Base ; 1-[Isopropylamino]-3-[1-naphthyloxy]-2-propanol ; 2-Propanol,1-(1-methylethyl)amino-3-(1-naphthalenyloxy)- ; 1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol ; 1-(1-Naphthyloxy)-3-(isopropylamino)-2-propanol ; 2-Propanol,1-(isopropylamino)-3-(1-naphthyloxy)- (7CI,8CI) ; 2-Propanol,1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)- (9CI) .When Inderal (525-66-6) was heated,it emits toxic fumes of NOx .This chemical is a crystals from Cyclohexane and it's slightly soluble in water.It is stable to heat, unstable to light.
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