CHEBI:8405 - primaquine

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ChEBI Name primaquine
ChEBI ID CHEBI:8405
Definition An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N4 position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:110389
Supplier Information
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Formula C15H21N3O
Net Charge 0
Average Mass 259.34670
Monoisotopic Mass 259.168
InChI InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3
InChIKey INDBQLZJXZLFIT-UHFFFAOYSA-N
SMILES COc1cc(NC(C)CCCN)c2ncccc2c1
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): 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.
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ChEBI Ontology
Outgoing primaquine (CHEBI:8405) has role antimalarial (CHEBI:38068)
primaquine (CHEBI:8405) is a N-substituted diamine (CHEBI:50441)
primaquine (CHEBI:8405) is a aminoquinoline (CHEBI:36709)
primaquine (CHEBI:8405) is a aromatic ether (CHEBI:35618)
IUPAC Name
N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
INNs Sources
primaquina ChemIDplus
primaquine KEGG DRUG
primaquinum ChemIDplus
Synonyms Sources
6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline ChemIDplus
8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline NIST Chemistry WebBook
8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline ChemIDplus
Neo-Quipenyl DrugBank
Primachin DrugBank
Primachinum ChemIDplus
Primaquin ChemIDplus
Manual Xrefs Databases
2266 DrugCentral
C07627 KEGG COMPOUND
D08420 KEGG DRUG
DB01087 DrugBank
HMDB0015219 HMDB
LSM-1649 LINCS
Primaquine Wikipedia
View more database links
Registry Numbers Types Sources
19337 Beilstein Registry Number Beilstein
19337 Reaxys Registry Number Reaxys
751542 Gmelin Registry Number Gmelin
90-34-6 CAS Registry Number KEGG COMPOUND
90-34-6 CAS Registry Number ChemIDplus
90-34-6 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
10928454 PubMed citation Europe PMC
11303037 PubMed citation Europe PMC
12036132 PubMed citation Europe PMC
14917959 PubMed citation Europe PMC
15494911 PubMed citation Europe PMC
16537060 PubMed citation Europe PMC
17253504 PubMed citation Europe PMC
18930565 PubMed citation Europe PMC
19114311 PubMed citation Europe PMC
2210868 PubMed citation Europe PMC
28279180 PubMed citation Europe PMC
28289025 PubMed citation Europe PMC
8920977 PubMed citation Europe PMC
Last Modified
17 March 2017