SynCED: Mesoridazine

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:59 UTC

Update Date

2026-05-14 16:53:15 UTC

Accession Number

CHEM002304

Identification

Common Name

Mesoridazine

Class

Small Molecule

Description

Mesoridazine is only found in individuals that have used or taken this drug. It is a phenothiazine antipsychotic with effects similar to chlorpromazine. [PubChem]Based upon animal studies, mesoridazine, as with other phenothiazines, acts indirectly on reticular formation, whereby neuronal activity into reticular formation is reduced without affecting its intrinsic ability to activate the cerebral cortex. In addition, the phenothiazines exhibit at least part of their activities through depression of hypothalamic centers. Neurochemically, the phenothiazines are thought to exert their effects by a central adrenergic blocking action.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Antipsychotic Agent
Dopamine Antagonist
Drug
Ether
Metabolite
Organic Compound
Phenothiazine
Synthetic Compound

Chemical Structure

MOL SDF 3D SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
10-(2(1-Methyl-2-piperidyl)ethyl)-2-(methylsulfinyl)phenothiazine	ChEBI
10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylsulfinyl phenothiazine	ChEBI
2-Methanesulfinyl-10-[2-(1-methyl-piperidin-2-yl)-ethyl]-10H-phenothiazine	ChEBI
Mesoridazina	ChEBI
Mesoridazinum	ChEBI
Thioridazine thiomethyl sulfoxide	ChEBI
Thioridazine-2-sulfoxide	ChEBI
TPS-23	ChEBI
Lidanar	Kegg
10-(2(1-Methyl-2-piperidyl)ethyl)-2-(methylsulphinyl)phenothiazine	Generator
10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylsulphinyl phenothiazine	Generator
2-Methanesulphinyl-10-[2-(1-methyl-piperidin-2-yl)-ethyl]-10H-phenothiazine	Generator
Thioridazine thiomethyl sulphoxide	Generator
Thioridazine-2-sulphoxide	Generator
Thioridazien thiomethyl sulfoxide	HMDB
Thioridazine monosulfoxide analog	HMDB
TPS23	HMDB
Serentil	HMDB

Chemical Formula

C₂₁H₂₆N₂OS₂

Average Molecular Mass

386.574 g/mol

Monoisotopic Mass

386.149 g/mol

CAS Registry Number

5588-33-0

IUPAC Name

2-methanesulfinyl-10-[2-(1-methylpiperidin-2-yl)ethyl]-10H-phenothiazine

Traditional Name

mesoridazine

SMILES

CN1CCCCC1CCN1C2=CC=CC=C2SC2=C1C=C(C=C2)S(C)=O

InChI Identifier

InChI=1S/C21H26N2OS2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(26(2)24)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3

InChI Key

SLVMESMUVMCQIY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

Alternative Parents

Substituents

Phenothiazine
Alkyldiarylamine
Diarylthioether
Aryl thioether
Tertiary aliphatic/aromatic amine
Para-thiazine
Piperidine
Benzenoid
Sulfoxide
Tertiary amine
Tertiary aliphatic amine
Thioether
Sulfinyl compound
Azacycle
Amine
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:6780 )
tertiary amino compound (CHEBI:6780 )
sulfoxide (CHEBI:6780 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

dopaminergic antagonist

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	7.67e-02 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.077 g/L	ALOGPS
logP	3.83	ALOGPS
logP	3.57	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	19.36	ChemAxon
pKa (Strongest Basic)	8.19	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	115.13 m³·mol⁻¹	ChemAxon
Polarizability	43.83 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Oral; Intramuscular injection. Well absorbed from the gastrointestinal tract.

Mechanism of Toxicity

Based upon animal studies, mesoridazine, as with other phenothiazines, acts indirectly on reticular formation, whereby neuronal activity into reticular formation is reduced without affecting its intrinsic ability to activate the cerebral cortex. In addition, the phenothiazines exhibit at least part of their activities through depression of hypothalamic centers. Neurochemically, the phenothiazines are thought to exert their effects by a central adrenergic blocking action.

Metabolism

Half Life: 24 to 48 hours

Toxicity Values

Oral LD₅₀ is 560 ± 62.5 mg/kg and 644 ± 48 mg/kg in mouse and rat, respectively.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used in the treatment of schizophrenia, organic brain disorders, alcoholism and psychoneuroses.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose may include emesis, muscle tremors, decreased food intake and death associated with aspiration of oral-gastric contents into the respiratory system.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00933

HMDB ID

HMDB0015068

FooDB ID

Not Available

Phenol Explorer ID