primaquine

CHEBI:8405 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:35618 CHEBI:35618
CHEBI:36709 CHEBI:36709
CHEBI:50441 CHEBI:50441

Chemical structure

Computed structure properties
Molecular formula	C15H21N3O
Charge	0
Average mass	259.353 Da
Monoisotopic mass	259.16846 Da
Source	ChEBI
InChIKey	INDBQLZJXZLFIT-UHFFFAOYSA-N

SMILES

COc1cc(NC(C)CCCN)c2ncccc2c1

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

Also called

primaquina (INN)— chebi
primaquinum (INN)— chebi
N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine (EXACT_SYNONYM)— chebi
6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline (EXACT_SYNONYM)— chebi
8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline (EXACT_SYNONYM)— chebi
8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline (EXACT_SYNONYM)— chebi
Neo-Quipenyl (EXACT_SYNONYM)— chebi
Primachin (EXACT_SYNONYM)— chebi
Primachinum (EXACT_SYNONYM)— chebi
Primaquin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:90-34-6
drugbank:DB01087
drugcentral:2266
gmelin:751542
hmdb:HMDB0015219
kegg.compound:C07627
kegg.drug:D08420
lincs.smallmolecule:LSM-1649
reaxys:19337
wikipedia.en:Primaquine

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:38068 CHEBI:38068

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:8405`	primaquine	`antibioticmech:chebi-7a24dddf23`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.