quinacrine (CHEBI:8711)

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ChEBI Name	quinacrine

ChEBI ID	CHEBI:8711

Definition	A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.

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

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Formula

C23H30ClN3O

Net Charge

Average Mass

399.95700

Monoisotopic Mass

399.20774

InChI

InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)

InChIKey

GPKJTRJOBQGKQK-UHFFFAOYSA-N

SMILES

CCN(CC)CCCC(C)Nc1c2ccc(Cl)cc2nc2ccc(OC)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):	EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor An EC 1.8.1.* (oxidoreductase acting on sulfur group of donors, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of trypanothione-disulfide reductase (EC 1.8.1.12). antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.

Application(s):	antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.

ChEBI Ontology
Outgoing	quinacrine (CHEBI:8711) has parent hydride acridine (CHEBI:36420) quinacrine (CHEBI:8711) has role antimalarial (CHEBI:38068) quinacrine (CHEBI:8711) has role EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor (CHEBI:77402) quinacrine (CHEBI:8711) is a acridines (CHEBI:22213) quinacrine (CHEBI:8711) is a aromatic ether (CHEBI:35618) quinacrine (CHEBI:8711) is a organochlorine compound (CHEBI:36683) quinacrine (CHEBI:8711) is a tertiary amino compound (CHEBI:50996)

Incoming	quinacrine mustard (CHEBI:37595) has functional parent quinacrine (CHEBI:8711) (R)-quinacrine (CHEBI:49845) is a quinacrine (CHEBI:8711) (S)-quinacrine (CHEBI:37597) is a quinacrine (CHEBI:8711)

IUPAC Name

4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine

Synonyms	Sources
2-methoxy-6-chloro-9-diethylaminopentylaminoacridine	ChemIDplus
3-chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine	ChemIDplus
6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine	ChemIDplus
Mepacrine	KEGG COMPOUND
mepacrine	ChemIDplus
N⁴-(6-chloro-2-methoxy-9-acridinyl)-N¹,N¹-diethyl-1,4-pentanediamine	ChemIDplus
Quinacrine	KEGG COMPOUND

Last Modified

22 February 2017