9-PHENANTHROL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H10O
Molecular Weight	194.2286
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC2=CC=CC=C2C3=C1C=CC=C3

InChI

InChIKey=DZKIUEHLEXLYKM-UHFFFAOYSA-N

InChI=1S/C14H10O/c15-14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9,15H

HIDE SMILES / InChI

Molecular Formula	C14H10O
Molecular Weight	194.2286
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24433510 | https://www.ncbi.nlm.nih.gov/pubmed/18297105 | https://www.ncbi.nlm.nih.gov/pubmed/25573456 | https://www.ncbi.nlm.nih.gov/pubmed/23936231 | https://www.ncbi.nlm.nih.gov/pubmed/24037125

9-Phenanthrol is a small molecule capable of modulating vascular and smooth muscle contractility through inhibition of the TRMP4 and Anoctamin-1 Ca(2+) channels. This mechanism of action has suggested implications for ischemic injuries to the heart and brain, as well as control over the excitability of vascular smooth muscle and urinary bladder smooth muscle.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Transient receptor potential cation channel subfamily M member 4 3 Target ID: Q8TD43 Gene ID: 54795.0 Gene Symbol: TRPM4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24433510	Inhibitor 8504		17.0 µM [IC50]
Anoctamin-1 5 Target ID: Q5XXA6 Gene ID: 55107.0 Gene Symbol: ANO1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25573456	Inhibitor 8504		12.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Cardiac ischaemia-reperfusion 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24433510	Primary	Basic research	Unknown Approved Use Unknown
Ischemic stroke injury 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24433510	Primary	Basic research	Unknown Approved Use Unknown
Diabetes mellitus 93 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29098165	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The TRPM4 channel inhibitor 9-phenanthrol.	2014-04	24433510
Differential action of monohydroxylated polycyclic aromatic hydrocarbons with estrogen receptors α and β.	2013-04	22989670
Coordination in phenanthrene biodegradation: pyruvate as microbial demarcation.	2010-12	20931171
Pharmacological inhibition of TRPM4 hyperpolarizes vascular smooth muscle.	2010-11	20826763
Genome-to-function characterization of novel fungal P450 monooxygenases oxidizing polycyclic aromatic hydrocarbons (PAHs).	2010-09-03	20674550
Ca2+ release from the sarcoplasmic reticulum is required for sustained TRPM4 activity in cerebral artery smooth muscle cells.	2010-08	20427713
Synthesis of phenanthrone derivatives from sec-alkyl aryl ketones and aryl halides via a palladium-catalyzed dual C-H bond activation and enolate cyclization.	2010-06-30	20524609
Rapid simultaneous analysis of 1-hydroxypyrene, 2-hydroxyfluorene, 9-hydroxyphenanthrene, 1- and 2-naphthol in urine by first derivative synchronous fluorescence spectrometry using Tween-20 as a sensitizer.	2010-01-25	20103092
Urinary profiles to assess polycyclic aromatic hydrocarbons exposure in coke-oven workers.	2010-01-15	20143505
Using gold nanoparticles to improve the recovery and the limits of detection for the analysis of monohydroxy-polycyclic aromatic hydrocarbons in urine samples.	2009-07-31	19559440
Using liquid chromatography-tandem mass spectrometry to quantify monohydroxylated metabolites of polycyclic aromatic hydrocarbons in urine.	2009-04-15	19299209
Synchronous fluorescence determination of urinary 1-hydroxypyrene, beta-naphthol and 9-hydroxyphenanthrene based on the sensitizing effect of beta-cyclodextrin.	2009-03-16	19231355
Involuntary tobacco smoke exposure and urinary levels of polycyclic aromatic hydrocarbons in the United States, 1999 to 2002.	2009-03	19258471
Development of a gas chromatography/mass spectrometry method to quantify several urinary monohydroxy metabolites of polycyclic aromatic hydrocarbons in occupationally exposed subjects.	2008-11-15	18952507
Multigeneration exposure of the springtail Folsomia candida to phenanthrone: from dose-response relationships to threshold concentrations.	2008-09-15	18853820
Direct quantification of monohydroxy-polycyclic aromatic hydrocarbons in synthetic urine samples via solid-phase extraction-room-temperature fluorescence excitation-emission matrix spectroscopy.	2008-05-15	18358224
Enhanced reactivity of hydroxylated polycyclic aromatic hydrocarbons to birnessite in soil: reaction kinetics and nonextractable residue formation.	2008-05	18419188
Facilitating effects of metal cations on phenanthrone sorption in soils.	2008-04-01	18504974
9-phenanthrol inhibits human TRPM4 but not TRPM5 cationic channels.	2008-04	18297105
Proteasome-dependent pharmacological rescue of cystic fibrosis transmembrane conductance regulator revealed by mutation of glycine 622.	2008-04	18230692
Road pavers' occupational exposure to asphalt containing waste plastic and tall oil pitch.	2006-01	16395464
Quantification of several monohydroxylated metabolites of polycyclic aromatic hydrocarbons in urine by high-performance liquid chromatography with fluorescence detection.	2005-11	16184365
A different route to the synthesis of 9,10-disubstituted phenanthrenes.	2005-08-05	16050719
Determination of phenanthrene and hydroxyphenanthrenes in various biological matrices at trace levels using gas chromatography-mass spectrometry.	2005-04	15842760
Liquid chromatography-mass spectrometry analysis of hydroxylated polycyclic aromatic hydrocarbons, formed in a simulator of the human gastrointestinal tract.	2004-07-05	15171935
The importance of both charge exchange and proton transfer in the analysis of polycyclic aromatic compounds using atmospheric pressure chemical ionization mass spectrometry.	2004-03	14998532
Application of microscopic fungi isolated from polluted industrial areas for polycyclic aromatic hydrocarbons and pentachlorophenol reduction.	2003	12801095
Oxygen-containing functional groups on single-wall carbon nanotubes: NEXAFS and vibrational spectroscopic studies.	2001-10-31	11674002
Initial oxidative and subsequent conjugative metabolites produced during the metabolism of phenanthrene by fungi.	1996-04	8652115
Metabolism of phenanthrene by Phanerochaete chrysosporium.	1991-11	1781688
Stereoselective formation of a K-region dihydrodiol from phenanthrene by Streptomyces flavovirens.	1990	2222121
Topographic recognition of cyclic hydrocarbons and related compounds by receptors for androgens, estrogens, and glucocorticoids.	1987	3695475

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Tetracycline-inducible HEK-293 cells were transfected to express the human TRPM4 channel and cultured in DMEM supplemented with 10% fetal bovine serum and 2 mM glutamine under a 5% CO2 atmosphere at 37 deg-C. The growth media was further supplemented with 5 micro-g/mL S-blasticidin and 0.4 mg/mL Zeocin. Cells were resuspended in media containing 1 micro-g/mL tetracycline 18 - 22 hours before experimentation. Whole-cell currents were recorded using the inside out configuration of the voltage patch-clamp technique. TRPM4 currents were monitored with seven doses of 9-phenanthrol between 10^-8 to 10^-4 M. At 10^-4 M 9-phenanthrol almost totally inhibited the channel current. The fitting of the dose-response curves with the Hill equation yielded an IC50 in the range of 2 × 10−5 m and showed no voltage dependence of the drug effect.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:11:45 GMT 2025` Edited by `admin` on `Mon Mar 31 21:11:45 GMT 2025`
Record UNII	9FYU45OV9H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

9-PHENANTHROL

Systematic Name

English

NSC-50554

Preferred Name

English

Code System Code Type Description

ECHA (EC/EINECS)

207-602-4