phentolamine   Click here for help

GtoPdb Ligand ID: 502

Synonyms: dibasin | fentolamin | Regitine® | Rogitine®
Approved drug
phentolamine is an approved drug (FDA (1952))
Compound class: Synthetic organic
Comment: Phentolamine is a non-selective alpha-adrenergic receptor antagonist.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 47.86
Molecular weight 281.15
XLogP 3.26
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Cc1ccc(cc1)N(c1cccc(c1)O)CC1=NCCN1
Isomeric SMILES Cc1ccc(cc1)N(c1cccc(c1)O)CC1=NCCN1
InChI InChI=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 Key MRBDMNSDAVCSSF-UHFFFAOYSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
α1A-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 8.6 pKi - 3
pKi 8.6 [3]
α2A-adrenoceptor Hs Antagonist Antagonist 8.4 pKi - 1-2
pKi 8.4 [1-2]
α1D-adrenoceptor Primary target of this compound Hs Antagonist Inverse agonist 8.2 pKi - 3
pKi 8.2 [3]
α2B-adrenoceptor Hs Antagonist Antagonist 8.2 pKi - 1-2
pKi 8.2 [1-2]
α1A-adrenoceptor Rn Antagonist Antagonist 8.1 pKi - 4
pKi 8.1 [4]
α2C-adrenoceptor Hs Antagonist Antagonist 7.6 – 7.9 pKi - 1-2
pKi 7.6 – 7.9 [1-2]
α1B-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 7.5 pKi - 3
pKi 7.5 [3]