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Chemical substance record

Primaquine

90-34-6C15H21N3O259.353 g/mol
Organic/Inorganic Small MoleculeChEBI source record

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

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values
CAS number90-34-6ChEBI ↗
Molecular formulaC15H21N3OChEBI ↗
Molar mass259.353 g/molChEBI ↗
Monoisotopic mass259.16846 DaChEBI ↗
Formal charge0ChEBI ↗
ChEBI identifierCHEBI:8405ChEBI ↗

Cross-source molecular data

PubChem
Molar mass259.35 g/molPubChem ↗
Exact mass259.168462302 DaPubChem ↗
Computed XLogP2.2PubChem ↗
Topological polar surface area (Ų)60.2PubChem ↗
H-bond donors2PubChem ↗
H-bond acceptors4PubChem ↗
Rotatable bonds6PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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primaquine
N(4)-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
INDBQLZJXZLFIT-UHFFFAOYSA-N
COc1cc(NC(C)CCCN)c2ncccc2c1
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

Names & synonyms

N(4)-(6-methoxyquinolin-8-yl)pentane-1,4-diamineprimaquinaprimaquinum

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology
aromatic etherChEBI parent class · 35618 ↗aminoquinolineChEBI parent class · 36709 ↗N-substituted diamineChEBI parent class · 50441 ↗
etherorganic heterocyclic compoundorganic molecular entity

Roles recorded in ChEBI

antiviral agentantifungal agentantimalarialanti-obesity agent

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass
Equivalent amount
0.00385575 mol

Uses 259.353 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions
C
Carbon · 15 atoms
69.47%
N
Nitrogen · 3 atoms
16.20%
H
Hydrogen · 21 atoms
8.16%
O
Oxygen · 1 atom
6.17%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations
Primaquine interferes with membrane recycling from endosomes to the plasma membrane through a direct interaction with endosomes which does not involve neutralisation of endosomal pH nor osmotic swelling of endosomes. ↗European journal of cell biology · 2000 Jun · PMID 10928454
Primaquine-induced hemolytic anemia: formation and hemotoxicity of the arylhydroxylamine metabolite 6-methoxy-8-hydroxylaminoquinoline. ↗The Journal of pharmacology and experimental therapeutics · 2001 May · PMID 11303037
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Sources & record history

Checked 27 Sep 2026
EMBL-EBI ChEBI · CHEBI:8405

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

NCBI PubChem · CID 4908 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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