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13523-86-9 molecular structure
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[2-hydroxy-3-(1H-indol-4-yloxy)propyl](propan-2-yl)amine

ChemBase ID: 836
Molecular Formular: C14H20N2O2
Molecular Mass: 248.3208
Monoisotopic Mass: 248.15247789
SMILES and InChIs

SMILES:
O(CC(O)CNC(C)C)c1c2c([nH]cc2)ccc1
Canonical SMILES:
OC(COc1cccc2c1cc[nH]2)CNC(C)C
InChI:
InChI=1S/C14H20N2O2/c1-10(2)16-8-11(17)9-18-14-5-3-4-13-12(14)6-7-15-13/h3-7,10-11,15-17H,8-9H2,1-2H3
InChIKey:
JZQKKSLKJUAGIC-UHFFFAOYSA-N

Cite this record

CBID:836 http://www.chembase.cn/molecule-836.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
[2-hydroxy-3-(1H-indol-4-yloxy)propyl](propan-2-yl)amine
1-(1H-indol-4-yloxy)-3-[(propan-2-yl)amino]propan-2-ol
IUPAC Traditional name
[2-hydroxy-3-(1H-indol-4-yloxy)propyl](propan-2-yl)amine
pindolol
1-(1H-indol-4-yloxy)-3-(isopropylamino)propan-2-ol
Brand Name
Blockin L
Blocklin L
Calvisken
Cardilate
Decreten
Durapindol
Glauco-Visken
Pectobloc
Pinbetol
Pynastin
Visken
Synonyms
Prindolol
Visken
(+/-)-4-[2-Hydroxy-3-(isopropylamino)propoxy]indole
Apo-pindol
Decreten
Pectobloc
Betapindol
Prinodolol
Pindolol
1-(1H-Indol-4-yloxy)-3-(isopropylamino)-2-propanol
1-(1H-Indol-4-yloxy)-3-[(1-methylethyl)amino]-2-propanol
Pindolol
CAS Number
13523-86-9
EC Number
236-867-9
MDL Number
MFCD00010530
PubChem SID
160964299
46508362
24277795
PubChem CID
4828
CHEBI ID
8214
ATC CODE
C07AA03
CHEMBL
500
Chemspider ID
4662
DrugBank ID
DB00960
IUPHAR ligand ID
91
KEGG ID
D00513
Unique Ingredient Identifier
BJ4HF6IU1D
Wikipedia Title
Pindolol
Medline Plus
a684032

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.086726  H Acceptors
H Donor LogD (pH = 5.5) -1.5002506 
LogD (pH = 7.4) -0.5322574  Log P 1.6929811 
Molar Refractivity 71.462 cm3 Polarizability 29.42685 Å3
Polar Surface Area 57.28 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.17  LOG S -2.46 
Solubility (Water) 8.61e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.1 M HCl: soluble20 mg/mL expand Show data source
0.1 M NaOH: soluble0.2 mg/mL expand Show data source
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.2 mg/mL expand Show data source
7880 mg/L expand Show data source
DMSO expand Show data source
H2O: insoluble expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
white to off-white powder expand Show data source
Melting Point
165-167°C expand Show data source
167-171 °C(lit.) expand Show data source
Hydrophobicity(logP)
1.9 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
UB6660000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
Others expand Show data source
Admin Routes
oral, iv expand Show data source
Bioavailability
50% to 95% expand Show data source
Excretion
Renal expand Show data source
Half Life
3–4 hours expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
B (US) expand Show data source
C (Australia) expand Show data source
Gene Information
human ... ADRB1(153), HTR1A(3350) expand Show data source
Mechanism of Action
5HT1A serotonin receptor antagonist expand Show data source
Non-cardioselective beta-Adrenoceptor antagonist expand Show data source
Partial agonist expand Show data source
Possesses intrinsic sympathomimetic actions (ISA), but little membrane-stabilizing activity expand Show data source
Sympatholytic-Beta expand Show data source
Vasodilator expand Show data source
Purity
≥98% (TLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Used in treatment of Angina pectoris and hypertension expand Show data source
Vasodilator expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00960 external link
Item Information
Drug Groups approved
Description A moderately lipophilic beta blocker (adrenergic beta-antagonists). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638)
Indication For the management of hypertension, edema, ventricular tachycardias, and atrial fibrillation.
Pharmacology Pindolol is a non-selective beta-adrenergic antagonist (beta-blocker) which possesses intrinsic sympathomimetic activity (ISA) in therapeutic dosage ranges but does not possess quinidine-like membrane stabilizing activity. Pindolol impairs AV node conduction and decreases sinus rate and may also increase plasma triglycerides and decrease HDL-cholesterol levels. Pindolol is nonpolar and hydrophobic, with low to moderate lipid solubility. Pindolol has little to no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, pindolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action.
Toxicity LD50=263 mg/kg (orally in rats). Signs of overdose include excessive bradycardia, cardiac failure, hypotension, and bronchospasm.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. In man, 35% to 40% is excreted unchanged in the urine and 60% to 65% is metabolized primarily to hydroxy-metabolites which are excreted as glucuronides and ethereal sulfates.
Absorption Rapidly and reproducibly absorbed (bioavailability greater than 95%).
Half Life 3 to 4 hours
Protein Binding 40%
Elimination Pindolol undergoes extensive metabolism in animals and man. In man, 35% to 40% is excreted unchanged in the urine and 60% to 65% is metabolized primarily to hydroxy-metabolites which are excreted as glucuronides and ethereal sulfates. About 6% to 9% of an administered intravenous dose is excreted by the bile into the feces.
Distribution * 2 L/kg
Clearance * 50-300 mL/min [cirrhotic patients]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich - P0778 external link
Biochem/physiol Actions
β1-adrenoceptor antagonist; putative 5-HT1A serotonin receptor agonist; vasodilator.
Features and Benefits
Shelf-life of the powder is at least five years.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P0778.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - P468000 external link
Mixed β-adrenergic blocker and serotonin 5HT1A-receptor antagonist. Antihypertensive; antianginal; antiarrhythmic; antiglaucoma.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Dreshfield, L.J., et al.: Neurochem. Res., 21, 557 (1996)
  • • Perez, V., et al.: Lancet, 349, 1594 (1996)
  • • Giudicelli, J.F. et al., J. Pharmacol. Exp. Ther., 1969, 168, 116, (pharmacol)
  • • Rivier, J.-L. et al., Therapie, 1970, 25, 245, (pharmacol)
  • • Seemann, F. et al., Helv. Chim. Acta, 1971, 54, 2411, (synth)
  • • Kuhnert-Brandstaetter, M. et al., Sci. Pharm., 1974, 42, 234, (uv)
  • • Tsuda, Y. et al., Chem. Pharm. Bull., 1981, 29, 3593, (synth)
  • • Aellig, W.H., Am. Heart J., 1982, 104, 333, (rev, pharmacol)
  • • Frishman, W.H., N. Engl. J. Med., 1983, 308, 904, (rev, pharmacol)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 3266, (synonyms)
  • • Fuji, M. et al., Chem. Pharm. Bull., 1992, 40, 2353, (synth, pmr, ms)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 637
  • • Ishibashi, H. et al., Chem. Pharm. Bull., 1994, 42, 271, (synth)
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, VSA000
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PATENTS

PATENTS

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INTERNET

INTERNET

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