Thiothixene (CED0009030)

Record Information

Version

1.0

Creation Date

2016-05-22 03:47:09 UTC

Update Date

2026-05-14 17:11:01 UTC

SynCED ID

CED0009030

Secondary Accession Numbers

CHEM016902

Identification

Common Name

Thiothixene

Class

Small Molecule

Description

Thiothixene is an organic compound with the formula C23H29N3O2S2 and an average molecular weight of 443.62 g/mol. Thiothixene belongs to the 1-benzothiopyrans, a subclass of benzothiopyrans within the organic compounds. This compound is recorded as being found in or released from healthcare, pharmaceuticals, and veterinary products, specifically as an antipsychotic. The recorded route of exposure is oral. Thiothixene acts on three protein targets, serving as an antagonist of the D(2) dopamine receptor (DRD2), the D(1A) dopamine receptor (DRD1), and the 5-hydroxytryptamine receptor 2A (HTR2A).

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N,N-Dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulphonamide	Generator
Pfizer brand OF tiotixene dihydrochloride	MeSH
Tiotixene	MeSH
Pfizer brand OF tiotixene	MeSH
Thiothixene	MeSH
Tiotixene pfizer brand	MeSH
Navane	MeSH

Chemical Formula

C₂₃H₂₉N₃O₂S₂

Average Molecular Mass

443.620 g/mol

Monoisotopic Mass

443.170 g/mol

CAS Registry Number

5591-45-7

IUPAC Name

N,N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulfonamide

Traditional Name

navan

SMILES

CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3C2=CCCN2CCN(C)CC2)C=C1

InChI Identifier

InChI=1S/C23H29N3O2S2/c1-24(2)30(27,28)18-10-11-23-21(17-18)19(20-7-4-5-9-22(20)29-23)8-6-12-26-15-13-25(3)14-16-26/h4-5,7-11,17H,6,12-16H2,1-3H3

InChI Key

GFBKORZTTCHDGY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thioxanthenes. These are organic polycyclic compounds containing a thioxanthene moiety, which is an aromatic tricycle derived from xanthene by replacing the oxygen atom with a sulfur atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiopyrans

Sub Class

1-benzothiopyrans

Direct Parent

Thioxanthenes

Alternative Parents

Substituents

Thioxanthene
Diarylthioether
Aryl thioether
N-alkylpiperazine
N-methylpiperazine
1,4-diazinane
Piperazine
Organosulfonic acid amide
Benzenoid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Tertiary amine
Tertiary aliphatic amine
Azacycle
Thioether
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	4.01	ALOGPS
logP	3.36	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	8.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.86 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	137.85 m³·mol⁻¹	ChemAxon
Polarizability	48.76 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0103900000-bf4826507276fd0fab3d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f6y-0419300000-b640f1110ae72a7103a7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-059i-9373000000-ad0d17f5724d06ea5fad	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0000900000-a2afb567b8b4ddb67d36	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0005-9207800000-429adb5832ee1e8650c0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052g-9200000000-c85846b09b6835e58111	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
607.0 Log mg/kg [340:1100]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000374	Antipsychotics?Antipsychotics are a class of synthetic chemicals used primarily for the treatment of psychiatric disorders, including schizophrenia and bipolar disorder.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem

Pathways

2 pathwaysPathway Source: PathBank

Thiothixene Dopamine Antagonist Action Pathway

Thiothixene Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	Prediction Confidence Score 0.41 Applicability Domain 0.516 Statistical Significance 0.0101 Supporting Reference Compounds 562 E-value 78.3942
Click to view 3D structure	D(1A) dopamine receptor	P18901	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.404 Applicability Domain 0.516 Statistical Significance 0.005 Supporting Reference Compounds 206 E-value 39.0803
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	Prediction Confidence Score 0.403 Applicability Domain 0.541 Statistical Significance 0.0085 Supporting Reference Compounds 536 E-value 66.0161
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.358 Applicability Domain 0.443 Statistical Significance 0.035 Supporting Reference Compounds 1103 E-value 272.55
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	Prediction Confidence Score 0.358 Applicability Domain 0.443 Statistical Significance 0.0261 Supporting Reference Compounds 861 E-value 202.953
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	Prediction Confidence Score 0.349 Applicability Domain 0.443 Statistical Significance 0.0196 Supporting Reference Compounds 507 E-value 152.662
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	Prediction Confidence Score 0.349 Applicability Domain 0.443 Statistical Significance 0.0144 Supporting Reference Compounds 425 E-value 112.259
Click to view 3D structure	Pleiotropic ABC efflux transporter of multiple drugs	P33302	Saccharomyces cerevisiae S288c	Predicted (SEA)	Prediction Confidence Score 0.338 Applicability Domain 0.443 Statistical Significance 3.10e-04 Supporting Reference Compounds 10 E-value 2.41333
Click to view 3D structure	Histamine H1 receptor	P31390	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.337 Applicability Domain 0.443 Statistical Significance 0.0028 Supporting Reference Compounds 63 E-value 21.7978
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.333 Applicability Domain 0.358 Statistical Significance 0.0442 Supporting Reference Compounds 955 E-value 344.016
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	Prediction Confidence Score 0.333 Applicability Domain 0.358 Statistical Significance 0.0338 Supporting Reference Compounds 823 E-value 263.364
Click to view 3D structure	D(1B) dopamine receptor	P21918	Humans	Predicted (SEA)	Prediction Confidence Score 0.331 Applicability Domain 0.443 Statistical Significance 0.0127 Supporting Reference Compounds 209 E-value 99.2578
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	Prediction Confidence Score 0.33 Applicability Domain 0.379 Statistical Significance 0.0331 Supporting Reference Compounds 528 E-value 257.525
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	Prediction Confidence Score 0.328 Applicability Domain 0.358 Statistical Significance 0.033 Supporting Reference Compounds 524 E-value 257.058
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.325 Applicability Domain 0.358 Statistical Significance 0.0334 Supporting Reference Compounds 541 E-value 260.016
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	Prediction Confidence Score 0.323 Applicability Domain 0.358 Statistical Significance 0.1037 Supporting Reference Compounds 1498 E-value 807.608
Click to view 3D structure	Histamine H3 receptor	Q9Y5N1	Humans	Predicted (SEA)	Prediction Confidence Score 0.319 Applicability Domain 0.443 Statistical Significance 0.0203 Supporting Reference Compounds 294 E-value 157.8
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	Prediction Confidence Score 0.316 Applicability Domain 0.358 Statistical Significance 0.0196 Supporting Reference Compounds 385 E-value 152.429
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P14842	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.316 Applicability Domain 0.345 Statistical Significance 0.0286 Supporting Reference Compounds 380 E-value 222.96
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.358 Statistical Significance 0.0384 Supporting Reference Compounds 686 E-value 299.252
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	Prediction Confidence Score 0.312 Applicability Domain 0.358 Statistical Significance 0.0312 Supporting Reference Compounds 487 E-value 243.201
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	Prediction Confidence Score 0.311 Applicability Domain 0.358 Statistical Significance 0.0398 Supporting Reference Compounds 593 E-value 309.996
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	Prediction Confidence Score 0.311 Applicability Domain 0.358 Statistical Significance 0.021 Supporting Reference Compounds 340 E-value 163.172
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	Prediction Confidence Score 0.311 Applicability Domain 0.358 Statistical Significance 0.0134 Supporting Reference Compounds 266 E-value 104.707
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	Prediction Confidence Score 0.311 Applicability Domain 0.358 Statistical Significance 0.0199 Supporting Reference Compounds 373 E-value 154.998