Zotepine (CED0008631)

Record Information

Version

1.0

Creation Date

2016-05-22 03:48:14 UTC

Update Date

2026-08-19 23:48:24 UTC

Accession Number

CHEM016941

Identification

Common Name

Zotepine

Class

Small Molecule

Description

Zotepine is an organic compound with the chemical formula C18H18ClNOS and an average molecular weight of 331.86 g/mol. Zotepine belongs to the dibenzothiepins, a subclass of benzothiepins within the organic compounds. It is further categorized under the superclass of organoheterocyclic compounds. The compound is found in or released from five recorded sources. These include household cleaning and consumer products, specifically tobacco product cases, non electric simulated smoking devices, and tobacco smoke filters. Additionally, it is associated with electrically stimulated smoking devices within the electrical and electronic equipment category, as well as processing meats in the food, food processing and cookware category. In terms of biological activity, zotepine interacts with eight recorded protein targets. It acts as an antagonist and inhibitor of the D(2) dopamine receptor (DRD2), the D(1A) dopamine receptor (DRD1), the D(1B) dopamine receptor (DRD5), and the 5-hydroxytryptamine receptor 2A (HTR2A), in addition to four other proteins.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Chlor-11-(2-dimethylaminoaethoxy)-dibenzo(b,F)-thiepin	ChEBI
2-Chloro-11-(2-(dimethylamino)ethoxy)dibenzo(b,F)thiepin	ChEBI
Lodopin	ChEBI
Setous	ChEBI
Zotepina	ChEBI
Zotepinum	ChEBI
Zoleptil	MeSH
2-chloro-11-(2-Dimethylaminoethoxy)dibenzo(b,F)thiepine	MeSH
Nipolept	MeSH

Chemical Formula

C₁₈H₁₈ClNOS

Average Molecular Mass

331.860 g/mol

Monoisotopic Mass

331.080 g/mol

CAS Registry Number

26615-21-4

IUPAC Name

[2-({6-chloro-2-thiatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-9-yl}oxy)ethyl]dimethylamine

Traditional Name

compound-4

SMILES

CN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C12

InChI Identifier

InChI=1S/C18H18ClNOS/c1-20(2)9-10-21-16-11-13-5-3-4-6-17(13)22-18-8-7-14(19)12-15(16)18/h3-8,11-12H,9-10H2,1-2H3

InChI Key

HDOZVRUNCMBHFH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzothiepins. Dibenzothiepins are compounds containing a dibenzothiepin moiety, which consists of two benzene connected by a thiepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiepins

Sub Class

Dibenzothiepins

Direct Parent

Dibenzothiepins

Alternative Parents

Substituents

Dibenzothiepin
Diarylthioether
Aryl thioether
Aryl chloride
Aryl halide
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Thioether
Organic oxygen compound
Amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:32316 )
dibenzothiepine (CHEBI:32316 )

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	0.00078 g/L	ALOGPS
logP	4.74	ALOGPS
logP	4.51	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	8.92	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.61 m³·mol⁻¹	ChemAxon
Polarizability	36.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4i-9000000000-80e02fa4b206648fd60e	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1009000000-96045d6ac7460e729f34	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9124000000-514ffa2cfc3d46bf4d11	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-076r-9510000000-1a60fee5bb74f9f306c1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0039000000-3caf4f9bea17829913e4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a59-0095000000-c0ec1fc18f181403f5aa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1190000000-8eaef1c160ca62b1cb73	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
241.0	Log mg/kg	[140:430]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
552	Processing Meats	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
567	Tobacco Product Cases	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
649	Pins Clothes	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Zotepine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	13.7015
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	36.2777
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	54.4945
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	16.1148
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	41.7272
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	61.423
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	6.46149
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	42.0386
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	103.228
Click to view 3D structure	Protein deacetylase HDAC6	Q9UBN7	Humans	Predicted (SEA)	74.4239
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	96.2216
Click to view 3D structure	Pleiotropic ABC efflux transporter of multiple drugs	P33302	Saccharomyces cerevisiae S288c	Predicted (SEA)	1.79053
Click to view 3D structure	Histamine H1 receptor	P31390	Rattus norvegicus	Predicted (SEA)	24.9896
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	257.058
Click to view 3D structure	D(1A) dopamine receptor	P18901	Rattus norvegicus	Predicted (SEA)	114.594
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	236.428
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	125.337
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	72.5555
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	166.753
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	107.743
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	85.4006
Click to view 3D structure	Histamine H3 receptor	Q9Y5N1	Humans	Predicted (SEA)	143.009
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	251.687
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	321.673
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	124.714