Phentolamine (CED0003496)

Record Information
Version1.0
Creation Date2016-05-22 03:44:54 UTC
Update Date2026-05-14 16:46:14 UTC
Accession NumberCHEM016830
Identification
Common NamePhentolamine
ClassSmall Molecule
Description
Phentolamine is an organic compound with the chemical formula C17H19N3O and an average molecular weight of 281.35 g/mol. Phentolamine belongs to the amines, a subclass of organonitrogen compounds within the organic compounds. The compound is associated with ten recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is found in peripheral vasodilators and unclassified therapeutic products. It is also present in food preservation within food, food processing, and cookware. Other sources include electrical and electronic equipment, such as radio transmission systems, antennas, and electrically stimulated smoking devices, as well as household cleaning and consumer products, including tobacco smoke filters, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices. Recorded exposure routes for phentolamine include intravenous, intramuscular, parenteral, submucosal, and ophthalmic administration. At the molecular level, phentolamine interacts with eight recorded protein targets. It functions as an antagonist/blocker of the Alpha-1A adrenergic receptor (ADRA1A), Alpha-1B adrenergic receptor (ADRA1B), Alpha-1D adrenergic receptor (ADRA1D), and Alpha-2A adrenergic receptor (ADRA2A), in addition to four other proteins.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2-(N-(m-Hydroxyphenyl)-p-toluidinomethyl)imidazolineChEBI
FentolaminaChEBI
Phentolamine mesylateChEBI
PhentolaminumChEBI
RegitinaChEBI
RegitineChEBI
RogitineChEBI
Phentolamine mesylic acidGenerator
RegitynHMDB
Novartis brand OF phentolamine mesylateHMDB
Paladin brand OF phentolamine mesylateHMDB
Phentolamine mono hydrochlorideHMDB
Phentolamine mono-hydrochlorideHMDB
Alliance brand OF phentolamine mesylateHMDB
Mesilate, phentolamineHMDB
Mesylate, phentolamineHMDB
Phentolamine methanesulfonateHMDB
Schering-plough brand OF phentolamine mesylateHMDB
FentolaminHMDB
Methanesulfonate, phentolamineHMDB
mono-Hydrochloride, phentolamineHMDB
Phentolamine mesilateHMDB
Z-MaxHMDB
Chemical FormulaC17H19N3O
Average Molecular Mass281.352 g/mol
Monoisotopic Mass281.153 g/mol
CAS Registry Number50-60-2
IUPAC Name3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol
Traditional Namephentolamine
SMILESCC1=CC=C(C=C1)N(CC1=NCCN1)C1=CC(O)=CC=C1
InChI IdentifierInChI=1S/C17H19N3O/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-17)15-3-2-4-16(21)11-15/h2-8,11,21H,9-10,12H2,1H3,(H,18,19)
InChI KeyMRBDMNSDAVCSSF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAlkyldiarylamines
Alternative Parents
Substituents
  • Alkyldiarylamine
  • M-aminophenol
  • Aminophenol
  • Aminotoluene
  • Aniline or substituted anilines
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Toluene
  • Monocyclic benzene moiety
  • Imidolactam
  • Benzenoid
  • 2-imidazoline
  • Amidine
  • Carboxylic acid amidine
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility0.27 g/LALOGPS
logP2.91ALOGPS
logP2.52ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.78ChemAxon
pKa (Strongest Basic)9.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area47.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity84.25 m³·mol⁻¹ChemAxon
Polarizability31.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0002-2950000000-98d994688cae92ea0a0bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0072-7953000000-578fe075a00a7a4d02b0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-4890000000-37817fa5f0f18f71350dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0090000000-f5257bc5fc7ab80d6c86Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-6190000000-51ab45cfce6d6cf7bc94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0znd-7920000000-bcc3e60235210d193abcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0090000000-39ce2b3898232204803dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1190000000-18c4ef9ee29cd0bea9d1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-9650000000-7b0c9ea52c5b916cb6c9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0090000000-0db20202647f4f8a9de6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1090000000-83d909204d9b8366fffcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-008c-7960000000-dcf271875addd4ab9fbdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0090000000-18e93f9625f62017f8e6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0930000000-b6e55971aac85aabe446Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006t-0900000000-52d5bc155c2a85191934Not 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
766.0Log mg/kg[430:1400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
291Peripheral vasodilatorsHealthcare, pharmaceuticals & veterinary productsNot Available
409Unclassified therapeutic productsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, 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
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAlpha-2A adrenergic receptorQ28838Bos taurusPredicted (SEA)0.700643
Nischarin structureClick to view 3D structureNischarinQ9Y2I1HumansPredicted (SEA)1.01204
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)23.3548
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)12.2223
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansPredicted (SEA)16.2705
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)12.923
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)17.1268
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)11.9109
Click to view 3D structureAlpha-1A adrenergic receptorP43140Rattus norvegicusPredicted (SEA)26.6244
Click to view 3D structureAlpha-1B adrenergic receptorP15823Rattus norvegicusPredicted (SEA)8.64126
Click to view 3D structureAlpha-1A adrenergic receptorP18130Bos taurusPredicted (SEA)10.6653
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)75.4359
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)111.402
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)79.4062
Click to view 3D structureAlpha-1D adrenergic receptorP23944Rattus norvegicusPredicted (SEA)13.3122
Click to view 3D structureAlpha-1B adrenergic receptorP18841Mesocricetus auratusPredicted (SEA)1.94623
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)66.7946
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)101.982
Click to view 3D structureAlpha-2A adrenergic receptorP22909Rattus norvegicusPredicted (SEA)19.0731
Click to view 3D structureNischarinQ4G017Rattus norvegicusPredicted (SEA)3.65891
5-hydroxytryptamine receptor 1D structureClick to view 3D structure5-hydroxytryptamine receptor 1DP28221HumansPredicted (SEA)150.327
Click to view 3D structureAlpha-1A adrenergic receptorO02824Oryctolagus cuniculusPredicted (SEA)13.7015
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansPredicted (SEA)182.167
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)510.924
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)758.641
Concentrations
Not Available
External Links
DrugBank IDDB00692
HMDB IDHMDB0014830
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhentolamine
Chemspider ID5571
ChEBI ID8081
PubChem Compound ID5775
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23438114
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23522530
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23658874
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23666670
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23887290
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23926134