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Basic Information
CAS No.: 525-66-6
Name: 1-Isopropylamino-3-(naphthalen-1-yloxy)-propan-2-ol
Article Data: 126
Molecular Structure:
Molecular Structure of 525-66-6 (1-Isopropylamino-3-(naphthalen-1-yloxy)-propan-2-ol)
Formula: C16H21 N O2
Molecular Weight: 259.348
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
EINECS: 208-378-0
Density: 1.093 g/cm3
Melting Point: 163-164 °C
Boiling Point: 434.9 °C at 760 mmHg
Flash Point: 216.8 °C
Solubility: Sol of 1 in 20 of water or alcohol; sltly sol in chloroform; practically insol in ether.
Appearance: White, odorless crystalline powder.
Hazard Symbols: Highly toxic.
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.
PSA: 41.49000
LogP: 2.96840
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;
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10476-53-6
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Chemistry

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℃

Uses

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

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.

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.

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.