(S)-(-)-Propranolol hydrochloride - CAS 4199-10-4
Category: Inhibitor
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Molecular Formula:
C16H21NO2.HCl
Molecular Weight:
295.81
COA:
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Targets:
Adrenergic Receptor
Description:
(S)-(-)-Propranolol is the more active enantiomer of the β-adrenoceptor antagonist propranolol. Propranolol is Beta 1 adrenergic receptor antagonist. It can be used for the treatment of high blood pressure, a number of types of irregular heart rate, thyrotoxicosis, capillary hemangiomas, performance anxiety, and essential tremors.
Appearance:
White to Yellow Cast powder
Synonyms:
(S)-(-)-1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol hydrochloride
Storage:
Store in a cool and dry place (or refer to the Certificate of Analysis).
MSDS:
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InChIKey:
ZMRUPTIKESYGQW-UQKRIMTDSA-N
InChI:
InChI=1S/C16H21NO2.ClH/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;1H/t14-;/m0./s1
Canonical SMILES:
CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O.Cl
1.Characterisation of beta2-adrenoceptors, using the agonist [11C]formoterol and positron emission tomography.
Visser TJ;van Waarde A;Doze P;Elsinga PH;van der Mark TW;Kraan J;Ensing K;Vaalburg W Eur J Pharmacol. 1998 Nov 13;361(1):35-41.
The agonist radioligand N-[2-hydroxy-5-[1-hydroxy-2-[[2-(4-[11C]-methoxyphenyl)-1-methylethyl]am ino]ethyl]phenyl]formamide ([11C]formoterol) was synthesised in order to test its ability to visualise pulmonary beta2-adrenoceptors in vivo, with positron emission tomography (PET). Formoterol was labelled via reaction of a dibenzyl-protected precursor with [11C]CH3I. Subsequent deprotection with Pd/C and H2 yielded [11C]formoterol in 5-15% (corrected for decay) and the specific activity ranged from 5.5-22.2 TBq mmol (150-600 Ci mmol(-1)), 60-70 min after end of bombardment. Biodistribution studies with [11C]formoterol were performed in male Wistar rats which were either untreated or predosed with (D,L)-propranolol hydrochloride (2.5 mg kg(-1), beta-adrenoceptor antagonist), erythro-DL-1-(7-methylindan-4-yloxy)-3-isopropylaminobuta n-2-ol hydrochloride (ICI 118551, 0.15 mg kg(-1), beta2-adrenoceptor antagonist), isoprenaline (15 mg kg(-1), non-subtype selective beta-adrenoceptor agonist) or (+/-)-(2-hydroxy-5-[2-((2-hydroxy-3-(4-((1-methyl-4-trifluoromethyl)1H-i midazol-2-yl-)phenoxy)propyl)amino)ethoxy]benzamide)monomethane sulfonate (CGP 20712A, 0.15 mg kg(-1), beta1-adrenoceptor antagonist).
2.Inhibition of (-)-propranolol hydrochloride by its enantiomer in white mice.
Kuzeff RM;Topashka-Ancheva MN;Mecheva RP Forsch Komplementarmed Klass Naturheilkd. 2003 Dec;10(6):309-14.
BACKGROUND: ;This study is based on the hypothesis, that the toxic or physiological effects of an optical isomer may be counteracted or reversed by the administration of a potentized preparation of one of its stereoisomers. In the present study the enantiomer was used.;METHODS: ;154 ICR conventional mice were used. 77 mice were administered (R)-(+)-propranolol HCl homeopathic potency prior to and during the experiment, and the other 77 were administered indistinguishable placebo. On the day of the experiment the mice were sedated with intraperitoneal Rometar. Once sedated they were injected intraperitoneally with the LD50 dose of (S)-(-)-propranolol HCl.;RESULTS: ;The end point for statistical analysis was the difference in survival between the placebo and treatment mice. The odds ratio for survival of treatment mice relative to placebo mice was 1.64. The hypothesis of equal survival proportions gave a chi-square of 2.0916 (1 degree of freedom), which has a p-value of 0.1481. The analysis was then adjusted for mouse weight and intraperitoneal (-)-propranolol dosage using a logistic regression (LR) model. The LR treatment odds ratio was 2.017 and the LR treatment chi-square was 2.8864 (1 degree of freedom), which has a p-value of 0.
3.Synthesis and biodistribution of [11c]procaterol, a beta2-adrenoceptor agonist for positron emission tomography.
Visser TJ;van der Wouden EA;van Waarde A;Doze P;Elsinga PH;Vaalburg W Appl Radiat Isot. 2000 Apr;52(4):857-63.
The potent, subtype-selective radioligand (+/-)-erythro-5-(1-hydroxy-2-[11C]isopropyl-aminobutyl)-8-hydroxy-car bostyril ([11C]procaterol) was synthesized and evaluated for visualization of pulmonary beta2-adrenoceptors with positron emission tomography (PET). Procaterol was labelled by reductive alkylation of the desisopropyl precursor with [11C]acetone under the influence of NaCNBH3 and acetic acid. Synthesis and HPLC purification were performed in 34 min. Specific activities ranged from 26.5-39.3 TBq (about 700-1000 Ci)/mmol and the radiochemical yield was 2.4-8.6% (corrected for decay). Biodistribution studies were performed in male Wistar rats which were either untreated or predosed with (D,L)-propranolol hydrochloride (beta-adrenoceptor antagonist, 2.5 mg/kg), ICI 118551 (beta2-adrenoceptor antagonist, 0.15 mg/kg), CGP 20712A (beta1-adrenoceptor antagonist, 0.15 mg/kg) or isoprenaline (beta1-adrenoceptor agonist, 15 mg/kg). Specific binding was observed in lungs, spleen and red blood cells, tissues known to contain beta2-adrenoceptors. Pulmonary binding was blocked by propranolol, ICI 118551 and isoprenaline, but not by CGP 20712A. This binding pattern is consistent with the beta2 selectivity of the radioligand.
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CAS 4199-10-4 (S)-(-)-Propranolol hydrochloride

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