U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H8ClNS
Molecular Weight 233.7181
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-CHLOROPHENOTHIAZINE

SMILES

c1ccc2c(c1)Nc3cc(ccc3S2)Cl

InChI

InChIKey=KFZGLJSYQXZIGP-UHFFFAOYSA-N
InChI=1S/C12H8ClNS/c13-8-5-6-12-10(7-8)14-9-3-1-2-4-11(9)15-12/h1-7,14H

HIDE SMILES / InChI

Molecular Formula C12H8ClNS
Molecular Weight 233.7181
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

2-chloro-phenothiazine is an important intermediate in the synthesis of anti-psychotic, anesthetic, anticonvulsant and other pharmaceutical drugs. 2-chlorophenothiazine exerts no effect on cellular bioenergetics and do not inhibit glioblastoma cell proliferation. In the photo-micronucleus test using V79 cells, 2-chlorophenothiazine was identified as photogenotoxin.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Inhibition of the mutagenicity and metabolism of 6-methyl-benzo[a]pyrene and 6-hydroxymethyl-benzo[a]pyrene.
1986 Jul 15
The application of the micronucleus test in Chinese hamster V79 cells to detect drug-induced photogenotoxicity.
1999 Sep 15
Synthesis and biological activity of N-acylphenothiazines.
2000 Apr
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Improved tricyclic inhibitors of trypanothione reductase by screening and chemical synthesis.
2009 Aug
Photodegradation of 2-chloro substituted phenothiazines in alcohols.
2009 Jan-Feb
Reversing the Warburg effect as a treatment for glioblastoma.
2013 Mar 29
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
At a 2-chlorophenothiazine (2Cl-PTH) concentration of 2 uM, an apparent 16-fold increase in Ks was observed for 6-methyl-benzo[a]pyrene (6-CH3-BaP). 2Cl-PTH might exert a strong effect on the metabolism of 6-CH3-BaP.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:13:04 UTC 2021
Edited
by admin
on Fri Jun 25 22:13:04 UTC 2021
Record UNII
95H3AO2301
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2-CHLOROPHENOTHIAZINE
Systematic Name English
PHENOTHIAZINE, 2-CHLORO-
Systematic Name English
NSC-170953
Code English
2-CL-PH
Common Name English
2-CHLORO-10H-PHENOTHIAZINE
Systematic Name English
CHLORPROMAZINE HYDROCHLORIDE IMPURITY E [EP]
Common Name English
NSC-67188
Code English
NSC-17469
Code English
2-CHLORO-PHENOTHIAZINE
Systematic Name English
Code System Code Type Description
PUBCHEM
7088
Created by admin on Fri Jun 25 22:13:05 UTC 2021 , Edited by admin on Fri Jun 25 22:13:05 UTC 2021
PRIMARY
CAS
92-39-7
Created by admin on Fri Jun 25 22:13:05 UTC 2021 , Edited by admin on Fri Jun 25 22:13:05 UTC 2021
PRIMARY
EPA CompTox
92-39-7
Created by admin on Fri Jun 25 22:13:05 UTC 2021 , Edited by admin on Fri Jun 25 22:13:05 UTC 2021
PRIMARY
ECHA (EC/EINECS)
202-152-5
Created by admin on Fri Jun 25 22:13:05 UTC 2021 , Edited by admin on Fri Jun 25 22:13:05 UTC 2021
PRIMARY
FDA UNII
95H3AO2301
Created by admin on Fri Jun 25 22:13:05 UTC 2021 , Edited by admin on Fri Jun 25 22:13:05 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP