chlorpromazine (CHEBI:3647)

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ChEBI Name	chlorpromazine

ChEBI ID	CHEBI:3647

Definition	A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB9319046, eMolecules:883948

Download	Molfile XML SDF

Wikipedia	License
2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C3H8O2 that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer: C2H5O+ + CH3OH → C3H8O2 + H+ 2-Methoxyethanol is used as a solvent for many different purposes such as varnishes, dyes, and resins. It is also used as an additive in airplane deicing solutions. In organometallic chemistry it is commonly used for the synthesis of Vaska's complex and related compounds such as carbonylchlorohydridotris(triphenylphosphine)ruthenium (II). During these reactions the alcohol acts as a source of hydride and carbon monoxide. 2-Methoxyethanol is toxic to the bone marrow and testicles. Workers exposed to high levels are at risk for granulocytopenia, macrocytic anemia, oligospermia, and azoospermia. The methoxyethanol is converted by alcohol dehydrogenase into methoxyacetic acid which is the substance which causes the harmful effects. Both ethanol and acetate have a protecting effect. The methoxyacetate can enter the Krebs cycle where it forms methoxycitrate.
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Formula

C17H19ClN2S

Net Charge

Average Mass

318.86400

Monoisotopic Mass

318.09575

InChI

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

InChIKey

ZPEIMTDSQAKGNT-UHFFFAOYSA-N

SMILES

CN(C)CCCN1c2ccccc2Sc2ccc(Cl)cc12

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	dopaminergic antagonist A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists. anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses. EC 3.4.21.26 (prolyl oligopeptidase) inhibitor Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26).

Application(s):	antiemetic A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors. dopaminergic antagonist A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists. phenothiazine antipsychotic drug

ChEBI Ontology
Outgoing	chlorpromazine (CHEBI:3647) has role anticoronaviral agent (CHEBI:149553) chlorpromazine (CHEBI:3647) has role antiemetic (CHEBI:50919) chlorpromazine (CHEBI:3647) has role dopaminergic antagonist (CHEBI:48561) chlorpromazine (CHEBI:3647) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779) chlorpromazine (CHEBI:3647) has role phenothiazine antipsychotic drug (CHEBI:37930) chlorpromazine (CHEBI:3647) is a organochlorine compound (CHEBI:36683) chlorpromazine (CHEBI:3647) is a phenothiazines (CHEBI:38093) chlorpromazine (CHEBI:3647) is a tertiary amine (CHEBI:32876)

Incoming	chlorpromazine N-oxide (CHEBI:3648) has functional parent chlorpromazine (CHEBI:3647) chlorpromazine hydrochloride (CHEBI:3649) has part chlorpromazine (CHEBI:3647)

IUPAC Name

3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine

Synonyms	Sources
3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethyl-1-propanamine	NIST Chemistry WebBook
3-(2-chlorophenothiazin-10-yl)-N,N-dimethyl-propan-1-amine	IUPHAR
Chlorpromazine	KEGG COMPOUND
CPZ	ChemIDplus
N-(3-dimethylaminopropyl)-3-chlorophenothiazine	ChemIDplus

Last Modified

23 April 2020