Pindolol (CED0005047)

Record Information
Version1.0
Creation Date2016-05-22 03:44:59 UTC
Update Date2026-08-19 06:52:52 UTC
Accession NumberCHEM016832
Identification
Common NamePindolol
ClassSmall Molecule
Description
Pindolol is an organic compound with the formula C14H20N2O2 and an average molecular weight of 248.32 g/mol. Pindolol belongs to the indoles, a subclass of indoles and derivatives within the organic compounds. This compound is recorded as being found in or released from 14 sources. Within healthcare, pharmaceuticals, and veterinary products, it is identified as a beta blocking agent. It is also found in drinking water and water supply, and in food, food processing, and cookware specifically regarding the preparation of wine or sparkling wine. Additional sources include household cleaning and consumer products such as perfumes within detergents and soaps, tobacco smoke filters, non electric simulated smoking devices, cigar cigarettes, and other smoking requisites. It is further associated with electrical and electronic equipment, including electrodes, radio transmission systems, amplifiers, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials. The recorded route of exposure for this compound is oral. Pindolol interacts with five recorded protein targets. It acts as an agonist, antagonist, or partial agonist of the Beta-1 adrenergic receptor (ADRB1), the Beta-2 adrenergic receptor (ADRB2), 5-hydroxytryptamine receptor 1A (HTR1A), and 5-hydroxytryptamine receptor 1B (HTR1B), as well as one other protein.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
1-(1H-indol-4-Yloxy)-3-(isopropylamino)propan-2-olChEBI
1-(1H-indol-4-Yloxy)-3-(propan-2-ylamino)-propan-2-olChEBI
1-(1H-indol-4-Yloxy)-3-[(1-methylethyl)amino]propan-2-olChEBI
4-(2-Hydroxy-3-isopropylaminopropoxy)-indoleChEBI
BetapindolChEBI
Blockin LChEBI
Blocklin LChEBI
Blocklin-LChEBI
CalviskenChEBI
CardilateChEBI
CarviskenChEBI
DecretenChEBI
DurapindolChEBI
Glauco-viskenChEBI
PectoblocChEBI
PinbetolChEBI
PindololumChEBI
PrinodololChEBI
PynastinChEBI
ViskenChEBI
Cardilic acidGenerator
LB 46HMDB
LB-46HMDB
PrindololHMDB
Chemical FormulaC14H20N2O2
Average Molecular Mass248.321 g/mol
Monoisotopic Mass248.152 g/mol
CAS Registry Number13523-86-9
IUPAC Name1-(1H-indol-4-yloxy)-3-[(propan-2-yl)amino]propan-2-ol
Traditional Name1-(1H-indol-4-yloxy)-3-(isopropylamino)propan-2-ol
SMILESCC(C)NCC(O)COC1=CC=CC2=C1C=CN2
InChI IdentifierInChI=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
InChI KeyJZQKKSLKJUAGIC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Alkyl aryl ether
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Azacycle
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.86 g/LALOGPS
logP2.17ALOGPS
logP1.69ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area57.28 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity71.46 m³·mol⁻¹ChemAxon
Polarizability28.27 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-9810000000-7bc0638a69aba25ecb87Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0089-9600000000-8fd11cc5a2fed5384868Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-2900000000-e773b852c7d4839b531dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01c3-1900000000-97bebf43acd96bd5cf5bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ba-0920000000-9c68ad2e49235b630737Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-0900000000-e0edd57b20d4dcecb440Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-1690000000-c5bffa0f5938ebc6de4bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-015c-0900000000-7208a6ab59379bc60e74Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-0900000000-762d3fea483c879a01e1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-2900000000-de1a6711be132a9bc406Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-007p-0900000000-c7b76abb87f901266e0cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00l6-0900000000-8b95aec2199af320261bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01c3-1900000000-97bebf43acd96bd5cf5bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0890000000-a3c20cc0c0efe2b51cfdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0090000000-9425d68d4cc59a32a43cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ba-0920000000-7f7959d21664f3e06a2eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-1490000000-8f45ac285bc25d656996Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00yi-7940000000-9107bd061a82704636c4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-060r-9400000000-da4f9e474bae11b0421cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000t-1790000000-f688d386b1973d57f378Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-cdd2bc6227637ee1b1faNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-2900000000-5d0d9df543fddaa5d1b8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-29275e6bc02f599a2d5eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-4890000000-dae8e1ddd1e40cf91067Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-9300000000-f3f457ae6618e846a110Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0940000000-e2efd23ab9a55ae84789Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-3900000000-3f95741c34f2779419f4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-2900000000-fe3e30deba49215e741cNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
622.0Log mg/kg[350:1100]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
293Beta blocking agentsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
5 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Beta-2 adrenergic receptor structureClick to view 3D structureBeta-2 adrenergic receptorP07550HumansPredicted (SEA)0.155698
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)0.934191
Beta-1 adrenergic receptor structureClick to view 3D structureBeta-1 adrenergic receptorP08588HumansPredicted (SEA)0.0778492
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)0.778492
Beta-3 adrenergic receptor structureClick to view 3D structureBeta-3 adrenergic receptorP13945HumansPredicted (SEA)0.0778492
Click to view 3D structure5-hydroxytryptamine receptor 1BP28564Rattus norvegicusPredicted (SEA)0.311397
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)5.52729
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansPredicted (SEA)4.20386
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)8.01847
Click to view 3D structureBeta-2 adrenergic receptorQ8K4Z4Cavia porcellusPredicted (SEA)1.32344
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)10.5875
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)15.9591
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)25.8459
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)18.606
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)9.809
Click to view 3D structureBeta-1 adrenergic receptorB0FL73Cavia porcellusPredicted (SEA)1.79053
Click to view 3D structureBeta-1 adrenergic receptorP18090Rattus norvegicusPredicted (SEA)1.71268
Click to view 3D structureSigma intracellular receptor 2Q5BJF2HumansPredicted (SEA)8.56341
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)26.0795
Click to view 3D structureBeta-2 adrenergic receptorQ28044Bos taurusPredicted (SEA)1.32344
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)64.9263
Click to view 3D structureBeta-1 adrenergic receptorP34971Mus musculusPredicted (SEA)1.16774
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)118.876
Click to view 3D structureBeta-2 adrenergic receptorP54833Canis lupus familiarisPredicted (SEA)0.856341
D(4) dopamine receptor structureClick to view 3D structureD(4) dopamine receptorP21917HumansPredicted (SEA)71.1542
Concentrations
Not Available
External Links
DrugBank IDDB00960
HMDB IDHMDB0015095
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPindolol
Chemspider ID4662
ChEBI ID8214
PubChem Compound ID4828
Kegg Compound IDC07445
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11022403
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11050366
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11185947
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11379796
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23020995