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.

Label unavailable CHEBI:35618
Label unavailable CHEBI:36709
Label unavailable 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Primaquine

Activity roles

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

antimalarial 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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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