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Propanalol
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Name

Propanalol

 EINECS 208-378-0
CAS No. 525-66-6 Density 1.093 g/cm3
PSA 41.49000 LogP 2.96840
Solubility Sol of 1 in 20 of water or alcohol; sltly sol in chloroform; practically insol in ether. Melting Point 163-164 °C
Formula C16H21 N O2 Boiling Point 434.9 °C at 760 mmHg
Molecular Weight 259.348 Flash Point 216.8 °C
Transport Information N/A Appearance White, odorless crystalline powder.
Safety 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. When heated to decomposition it emits toxic fumes of NOx. See also INDERAL HYDROCHLORIDE. Risk Codes N/A
Molecular Structure Molecular Structure of 525-66-6 (1-Isopropylamino-3-(naphthalen-1-yloxy)-propan-2-ol) Hazard Symbols Highly toxic.
Synonyms

2-Propanol,1-(isopropylamino)-3-(1-naphthyloxy)- (7CI,8CI); (?à)-Propranolol; 1-(1-Naphthyloxy)-3-(isopropylamino)-2-propanol;1-(Isopropylamino)-3-(1-naphthyloxy)-2-propanol;3-(Naphth-1-yloxy)-1-(isopropylamino)propan-2-ol; AY 64043; Betalong;DL-Propranolol; Euprovasin; Innopran XL; Propranolol; Proprasylyt; Racemicpropranolol; Reducor; dl-Propranolol; b-Propranolol

Article Data 126

Propanalol Synthetic route

91740-63-5

3-isopropyl-5-<(nphthyloxy)methyl>oxazolidin-2-one

525-66-6

propranolol

Conditions
ConditionsYield
With potassium hydroxide In benzene for 24h; Heating;100%
2461-42-9

3-(1-naphthyloxy)-1,2-epoxypropane

75-31-0

isopropylamine

525-66-6

propranolol

Conditions
ConditionsYield
With acetic acid In water at 20℃; for 8h;99%
In water94%
Stage #1: 3-(1-naphthyloxy)-1,2-epoxypropane With calcium chloride In acetonitrile
Stage #2: isopropylamine In acetonitrile Further stages.;		93%
2461-42-9

3-(1-naphthyloxy)-1,2-epoxypropane

79-46-9

2-nitropropane

525-66-6

propranolol

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In water at 20℃; for 24h; Inert atmosphere; Green chemistry;94%
90-15-3

α-naphthol

75-31-0

isopropylamine

106-89-8

epichlorohydrin

525-66-6

propranolol

Conditions
ConditionsYield
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.
2007-16-1

(RS)-1-bromo-3-(1-naphthyloxy)-2-propanol

75-31-0

isopropylamine

525-66-6

propranolol

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 40℃; for 4h; Solvent; Temperature;88.9%
2461-42-9

3-(1-naphthyloxy)-1,2-epoxypropane

75-31-0

isopropylamine

A

83314-78-7

N-Isopropyl-N,N-di-<3-(1-naphthoxy)-2-hydroxypropyl>amin

B

525-66-6

propranolol

Conditions
ConditionsYield
In toluene for 4h;A 60%
B n/a
82616-68-0

1-(3,4-Dihydro-naphthalen-1-yloxy)-3-isopropylamino-propan-2-ol

525-66-6

propranolol

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone59%
75-31-0

isopropylamine

2,2-Dichloro-3-(naphthalen-1-yloxymethyl)-oxirane

A

C24H20O2

B

C24H20O2

C

525-66-6

propranolol

Conditions
ConditionsYield
In tetrahydrofuranA n/a
B n/a
C 35%
20133-93-1

1-chloro-3-(1-naphthoxy)-2-propanol

75-31-0

isopropylamine

525-66-6

propranolol

129459-75-2

1-(isopropylamino)-3-(naphthalen-1-yloxy)propan-2-yl acetate

525-66-6

propranolol

Conditions
ConditionsYield
at 37℃; Rate constant; plasma intestine and liver of rats;

Propanalol Chemical Properties

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℃

Propanalol Uses

 Inderal (CAS NO.525-66-6) can be used for medication (vet).

Propanalol Toxicity Data With Reference

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.

Propanalol Safety Profile

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.

Propanalol Specification

 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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