ContaminantDB: Chlorpromazine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (44)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:01 UTC

Update Date

2026-05-14 16:39:59 UTC

Accession Number

CHEM002208

Identification

Common Name

Chlorpromazine

Class

Small Molecule

Description

The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class, chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking dopamine receptors. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.

Contaminant Sources

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

Contaminant Type

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

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(2-Chloro-10H-phenothiazin-10-yl)-N,N-dimethyl-1-propanamine	ChEBI
3-(2-Chlorophenothiazin-10-yl)-N,N-dimethyl-propan-1-amine	ChEBI
Aminazine	ChEBI
Chlorderazin	ChEBI
Chloropromazine	ChEBI
Chlorpromados	ChEBI
Chlorpromazinum	ChEBI
Clorpromazina	ChEBI
Contomin	ChEBI
CPZ	ChEBI
Largactil	ChEBI
N-(3-Dimethylaminopropyl)-3-chlorophenothiazine	ChEBI
Thorazine	ChEBI
Chlorazine	HMDB
Propaphenin	HMDB
Chlorpromazine hydrochloride	HMDB
Fenactil	HMDB
Chlordelazine	HMDB
Hydrochloride, chlorpromazine	HMDB

Chemical Formula

C₁₇H₁₉ClN₂S

Average Molecular Mass

318.864 g/mol

Monoisotopic Mass

318.096 g/mol

CAS Registry Number

50-53-3

IUPAC Name

[3-(2-chloro-10H-phenothiazin-10-yl)propyl]dimethylamine

Traditional Name

chlorpromazine

SMILES

CN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2

InChI Identifier

InChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3

InChI Key

ZPEIMTDSQAKGNT-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
Aryl chloride
Aryl halide
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Azacycle
Thioether
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:3647 )
tertiary amine (CHEBI:3647 )
organochlorine compound (CHEBI:3647 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

EC 3.4.21.26 (prolyl oligopeptidase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	177-178°C
Boiling Point	200-205°C at 8.00E-01 mm Hg
Solubility	2.55 mg/L (at 24°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	5.18	ALOGPS
logP	4.54	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	9.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.76 m³·mol⁻¹	ChemAxon
Polarizability	35.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	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	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4r-9053000000-9e1cc1d4fc6be5bc73b8	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-014i-2019000000-54e008f9fc11d7f45b68	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000i-9070000000-9bbe6c5123c891b9489b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4r-9053000000-9e1cc1d4fc6be5bc73b8	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-014i-2019000000-54e008f9fc11d7f45b68	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000i-9070000000-9bbe6c5123c891b9489b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-9161000000-fb3a39cba2075363c833	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0019000000-0028b3984b4c35e44def	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0090000000-800bf68c2158920c3f30	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03dj-0090000000-649e773296a3ecec2b04	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0190000000-7404aac4e28621b4f60a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-01b9-0019000000-993566c51e802e754da2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-1009000000-9e085e0019e6d749bec7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-9001000000-63215388b62ecefa2319	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0a4r-9000000000-0a622181e8ef22e69347	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-07vi-9100000000-c781f19efbf7f5bc080e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-014i-9000000000-a19b19eaa8aa053f7de7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-052r-9000000000-7c7616a9c48b6deec4ce	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03dj-0090000000-649e773296a3ecec2b04	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-066r-9200000000-6c03747eb04ed227c0fc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0a4i-0390000000-3ba26439eefecf96a16d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-03di-0190000000-911db04bc44a18aa9bcc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0090000000-800bf68c2158920c3f30	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0009000000-ed71cd0c4716568b4ed8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-03di-0190000000-7404aac4e28621b4f60a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0a4l-0890000000-0864e24ac7a3c6e8e6c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1029000000-7e34879597957c9ee39f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01bi-9076000000-5e7e6025c08ddac427f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059f-9320000000-af8b418201e78097c537	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0019000000-86aa9bde1ce82c180318	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-0393000000-613da71e073b4dd78512	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001j-3890000000-a4243a809dea08eb0af6	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9231000000-ed14fee152701eacf689	Spectrum

Toxicity Profile

Route of Exposure

Oral, Intravenous. Readily absorbed from the GI tract. Bioavailability varies due to first-pass metabolism by the liver.

Mechanism of Toxicity

Chlorpromazine acts as an antagonist (blocking agent) on different postsysnaptic receptors -on dopaminergic-receptors (subtypes D1, D2, D3 and D4 - different antipsychotic properties on productive and unproductive symptoms), on serotonergic-receptors (5-HT1 and 5-HT2, with anxiolytic, antidepressive and antiaggressive properties as well as an attenuation of extrapypramidal side-effects, but also leading to weight gain, fall in blood pressure, sedation and ejaculation difficulties), on histaminergic-receptors (H1-receptors, sedation, antiemesis, vertigo, fall in blood pressure and weight gain), alpha1/alpha2-receptors (antisympathomimetic properties, lowering of blood pressure, reflex tachycardia, vertigo, sedation, hypersalivation and incontinence as well as sexual dysfunction, but may also attenuate pseudoparkinsonism - controversial) and finally on muscarinic (cholinergic) M1/M2-receptors (causing anticholinergic symptoms like dry mouth, blurred vision, obstipation, difficulty/inability to urinate, sinus tachycardia, ECG-changes and loss of memory, but the anticholinergic action may attenuate extrapyramidal side-effects). Additionally, Chlorpromazine is a weak presynaptic inhibitor of Dopamine reuptake, which may lead to (mild) antidepressive and antiparkinsonian effects. This action could also account for psychomotor agitation and amplification of psychosis (very rarely noted in clinical use).

Metabolism

Extensively metabolized in the liver and kidneys. It is extensively metabolized by cytochrome P450 isozymes CYP2D6 (major pathway), CYP1A2 and CYP3A4. Approximately 10 to 12 major metabolite have been identified. Hydroxylation at positions 3 and 7 of the phenothiazine nucleus and the N-dimethylaminopropyl side chain undergoes demethylation and is also metabolized to an N-oxide. In urine, 20% of chlopromazine and its metabolites are excreted unconjugated in the urine as unchanged drug, demonomethylchlorpromazine, dedimethylchlorpromazine, their sulfoxide metabolites, and chlorpromazine-N-oxide. The remaining 80% consists of conjugated metabolites, principally O-glucuronides and small amounts of ethereal sulfates of the mono- and dihydroxy-derivatives of chlorpromazine and their sulfoxide metabolites. The major metabolites are the monoglucuronide of N-dedimethylchlorpromazine and 7-hydroxychlorpromazine. Approximately 37% of the administered dose of chlorpromazine is excreted in urine. Route of Elimination: Kidneys, ~ 37% excreted in urine Half Life: ~ 30 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

For the treatment of schizophrenia, control nausea and vomiting, For relief of restlessness and apprehension before surgery, adjunct in the treatment of tetanus, control the manifestations of the manic type of manic-depressive illness.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Agitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, restlessness

Treatment

Treatment is essentially symptomatic and supportive. Early gastric lavage is helpful. Keep patient under observation and maintain an open airway, since involvement of the extrapyramidal mechanism may produce dysphagia and respiratory difficulty in severe overdosage. Do not attempt to induce emesis because a dystonic reaction of the head or neck may develop that could result in aspiration of vomitus. Extrapyramidal symptoms may be treated with anti-parkinsonism drugs, barbiturates, or Benadryl. Care should be taken to avoid increasing respiratory depression. If administration of a stimulant is desirable, amphetamine, dextroamphetamine, or caffeine with sodium benzoate is recommended. Stimulants that may cause convulsions (e.g., picrotoxin or pentylenetetrazol) should be avoided. If hypotension occurs, the standard measures for managing circulatory shock should be initiated. If it is desirable to administer a vasoconstrictor, Levophed and Neo-Synephrine are most suitable. Other pressor agents, including epinephrine, are not recommended because phenothiazine derivatives may reverse the usual elevating action of these agents and cause a further lowering of blood pressure. (3)

Concentrations

Not Available

External Links

DrugBank ID

DB00477

HMDB ID

HMDB0014620

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID