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Name |
Atenolol |
EINECS | 249-451-7 |
CAS No. | 29122-68-7 | Density | 1.125 g/cm3 |
PSA | 84.58000 | LogP | 1.54330 |
Solubility | 0.3 mg/mL in water | Melting Point |
154 °C |
Formula | C14H22N2O3 | Boiling Point | 508.049 °C at 760 mmHg |
Molecular Weight | 266.34 | Flash Point | 261.059 °C |
Transport Information | N/A | Appearance | white to off-white crystalline solid |
Safety | 22-24/25-36-26 | Risk Codes | 22-36/37/38-20/21/22 |
Molecular Structure | Hazard Symbols | Xn | |
Synonyms |
Acetamide,2-[p-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]- (8CI);(RS)-Atenolol;Alinor;Altol;Anselol;Antipressan;Apo-Atenolol;AteHexal;Atecard;Atelol;Atenblock;Atendol;Atenet;Ateni;Ateno;Atenolol;Aterol;B-Vasc;Betacard;Tenormin;Tenormine;Tensimin;Tredol;Urosin;Vericordin;Xaten;1-p-Carbamoylmethylphenoxy-3-isopropylamino-2-propanol;Catenol;Catenolol;Corotenol;Farnormin;Hipres;ICI 66082;Internolol;Lo-ten;Lotenal;Normalol;Noten;Oraday;Prenormine;SelesBeta;Serten;Telol;Teno-basan;Tenolin;Tenoprin; |
Article Data | 14 |
Conditions | Yield |
---|---|
In water at 10℃; for 12h; | 95% |
1-(4'-cyanomethylphenoxy)-2-hydroxy-3-(isopropylamino)propane
(RS)-atenolol
Conditions | Yield |
---|---|
With bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) In ethanol; water for 72h; Reflux; | 93% |
(S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane
isopropylamine
(RS)-atenolol
Conditions | Yield |
---|---|
With Sulfated tungstate at 70℃; for 0.333333h; Green chemistry; | 90% |
Stage #1: (S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane; isopropylamine In N,N-dimethyl-formamide at 60℃; for 12h; Sealed tube; Stage #2: With water In N,N-dimethyl-formamide at 60℃; for 12h; Solvent; Temperature; Sealed tube; regioselective reaction; | 82.5% |
In methanol for 2h; Heating; Yield given; | |
In methanol at 20℃; for 20h; |
(RS)-atenolol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) Amberlite IRA-400 / 1.) H2O, 2.) MeOH, room temperature, 10 h 2: methanol / 2 h / Heating View Scheme |
(4-hydroxyphenyl)methanol
(RS)-atenolol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide 2: bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) / ethanol; water / 18 h / Reflux 3: piperidine / 6 h / 95 - 100 °C 4: methanol / 20 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide 2: piperidine / 6 h / 95 - 100 °C 3: methanol / 20 h / 20 °C / 760.05 Torr 4: bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) / ethanol; water / 72 h / Reflux View Scheme |
2-(4-hydroxyphenyl)acetamide
(RS)-atenolol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: piperidine / 6 h / 95 - 100 °C 2: methanol / 20 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: tetrabutylammomium bromide; sodium hydroxide / water / 50 h / 4 °C 2: water / methanol / 20 °C 3: water / 12 h / 10 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 24 h / Inert atmosphere; Reflux 2.1: N,N-dimethyl-formamide / 12 h / 60 °C / Sealed tube 2.2: 12 h / 60 °C / Sealed tube View Scheme |
4-cyanomethylphenol
(RS)-atenolol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) / ethanol; water / 18 h / Reflux 2: piperidine / 6 h / 95 - 100 °C 3: methanol / 20 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: piperidine / 6 h / 95 - 100 °C 2: methanol / 20 h / 20 °C / 760.05 Torr 3: bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) / ethanol; water / 72 h / Reflux View Scheme |
1-(4'-Cyanomethylphenoxy)-2,3-epoxypropane
(RS)-atenolol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol / 20 h / 20 °C / 760.05 Torr 2: bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) / ethanol; water / 72 h / Reflux View Scheme |
(S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane
(RS)-atenolol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: water / methanol / 20 °C 2: water / 12 h / 10 °C View Scheme |
1--2-acetoxy-3-chloropropane
(RS)-atenolol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; water / methanol / 2 h / 20 °C 2: water / 12 h / 10 °C View Scheme |
The IUPAC name of Atenolol is 2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide. With the CAS registry number 29122-68-7, it is also named as 1-p-Carbamoylmethylphenoxy-3-isopropylamino-2-propanol. The product's categories are Pharmaceutical; Intermediates & Fine Chemicals; Pharmaceuticals; API's; Adrenoceptor. Besides, it is white to off-white crystalline solid, which should be stored in tightly sealed container in a cool, dry place. And you should ensure that the workplaces have good ventilated or exhaust devices. In addition, its molecular formula is C14H22N2O3 and molecular weight is 266.34.
The other characteristics of this product can be summarized as: (1)EINECS: 249-451-7; (2)ACD/LogP: 0.34; (3)# of Rule of 5 Violations: 0; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 5; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 9; (11)Index of Refraction: 1.54; (12)Molar Refractivity: 74.257 cm3; (13)Molar Volume: 236.659 cm3; (14)Surface Tension: 45.019 dyne/cm; (15)Density: 1.125 g/cm3; (16)Flash Point: 261.059 °C; (17)Melting Point: 154 °C; (18)Enthalpy of Vaporization: 81.95 kJ/mol; (19)Boiling Point: 508.049 °C at 760 mmHg; (20)Solubility: H2O: 0.3 mg/mL; (21)Vapour Pressure: 0 mmHg at 25 °C.
Uses of Atenolol: this chemical is a selective β1 receptor antagonist, which is used primarily in cardiovascular diseases. It is also used for treatment of cardiovascular diseases and conditions such as hypertension, coronary heart disease, arrhythmias, angina (chest pain) and used to treat and reduce the risk of heart complications following myocardial infarction (heart attack). Additionally, it can be used for the treatment of symptoms of Graves Disease. Furthermore, it can be used to produce S(-)-Atenolol.
This reaction needs Rhizopus arrhizus, aq. Phosphate buffer and Butan-1-ol for 6 days. The yield is 75 %.
When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin and harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing to avoid contact with skin and eyes. Moreover, please do not breathe dust.
People can use the following data to convert to the molecule structure.
(1)SMILES: CC(C)NCC(COc1ccc(cc1)CC(=O)N)O
(2)InChI: InChI=1/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)
(3)InChIKey: METKIMKYRPQLGS-UHFFFAOYAT
(4)Std. InChI: InChI=1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)
(5)Std. InChIKey: METKIMKYRPQLGS-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | TDLo | oral | 10204ug/kg (10.204mg/kg) | BEHAVIORAL: COMA CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Anesthesiology. Vol. 83, Pg. 204, 1995. |
man | TDLo | oral | 49mg/kg/30D-I (49mg/kg) | BEHAVIORAL: EXCITEMENT | Journal of Clinical Pyschopharmacology. Vol. 6, Pg. 390, 1986. |
man | TDLo | oral | 86mg/kg/60D-I (86mg/kg) | BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)" | American Journal of Medicine. Vol. 85, Pg. 586, 1988. |
man | TDLo | oral | 129mg/kg/26W- (129mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: COUGH LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Annales de Medecine Interne. Vol. 148, Pg. 505, 1997. |
mouse | LD50 | intraperitoneal | 134mg/kg (134mg/kg) | Toksikologicheskii Vestnik. Vol. (4), Pg. 33, 1995. | |
mouse | LD50 | intravenous | 57mg/kg (57mg/kg) | PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4579, 1980. |
mouse | LD50 | oral | 2gm/kg (2000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4579, 1980. |
mouse | LD50 | subcutaneous | > 400mg/kg (400mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4579, 1980. | |
rabbit | LD50 | intravenous | 50mg/kg (50mg/kg) | Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 17, Pg. 425, 1979. | |
rat | LD50 | intravenous | 77mg/kg (77mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4579, 1980. |
rat | LD50 | oral | > 2gm/kg (2000mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4579, 1980. | |
rat | LD50 | subcutaneous | > 600mg/kg (600mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4579, 1980. | |
women | TDLo | oral | 16mg/kg (16mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION | Annals of Emergency Medicine. Vol. 14, Pg. 161, 1985. |
women | TDLo | oral | 42mg/kg/3W-I (42mg/kg) | British Medical Journal. Vol. 294, Pg. 1324, 1987. | |
women | TDLo | oral | 1080mg/kg/78W (1080mg/kg) | BLOOD: LEUKOPENIA MUSCULOSKELETAL: OTHER CHANGES SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Journal of Rheumatology. Vol. 13, Pg. 446, 1986. |