Compound: PRIMAQUINE
SMILES: O(c1cc(NC(CCCN)C)c2ncccc2c1)C
InChIKey: INDBQLZJXZLFIT-UHFFFAOYSA-N
Synonyms: PRIMAQUINE, 90-34-6, Primachin, 8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline, Neo-Quipenyl, Primaquin, Primachinum, Primaquina, Primaquinum, Kanaprim, Primachina, 1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)-, Maliride, 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine, 6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline, N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine, NSC-27296, CHEBI:8405, MVR3634GX1, 8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline, N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine, WR-2975, 8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline, SN-13272, DTXSID8023509, RefChem:56452, DTXCID903509, P01BA03, 201-987-2, (+/-)-Primaquine, SN 13,272, S. N. 13272, N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine, MFCD00598906, NSC 27296, Primaquine (INN), N4-(6-methoxy-8-quinolyl)pentane-1,4-diamine, N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine, 1,4-Pentanediamine, N(4)-(6-methoxy-8-quinolinyl)-, N-[(S)-4-Amino-1-methylbutyl]-6-methoxy-8-quinolinamine, Primachina [DCIT], dl-Primaquine, PRIMAQUINE [INN], Primaquine [INN:BAN], BRN 0019337, Maliride; NSC 27296; Neo-Quipenyl; Primachin, Primaquinum [INN-Latin], Primaquina [INN-Spanish], N~4~-(6-methoxyquinolin-8-yl)pentane-1,4-diamine, 6-Methoxy-8-[(4-amino-1-methylbutyl)amino]quinoline, Quinoline, 8-((4-amino-1-methylbutyl)amino)-6-methoxy-, CHEMBL506, MLS001334045, Kanaprim (TN), CCRIS 4109, HSDB 6516, n4-[6-methoxy-8-quinolinyl]-1,4-pentanediamine, 4-22-00-05817 (Beilstein Handbook Reference), NCGC00178754-06, SMR000875314, EINECS 201-987-2, 6-Methoxy-8-((4-amino-1-methylbutyl)amino)quinoline, Quinoline, 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-, UNII-MVR3634GX1, Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy, (RS)-primaquine, 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid, TG1-296, TG1-297, Primaquine Impurity 5, Spectrum_000830, PRIMAQUINE [MI], Prestwick0_000476, Prestwick1_000476, Prestwick2_000476, Prestwick3_000476, Spectrum2_000887, Spectrum3_000552, Spectrum4_000484, Spectrum5_001363, PRIMAQUINE [VANDF], Epitope ID:131792, PRIMAQUINE [WHO-DD], Oprea1_546209, SCHEMBL22207, BSPBio_000612, BSPBio_002223, KBioGR_000967, KBioSS_001310, DivK1c_000806, N(4)-(6-methoxyquinolin-8-yl)pentane-1,4-diamine, SPBio_000674, SPBio_002551, (+)-N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine, (-)-N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine, BPBio1_000674, cid_359247, GTPL9952, orb1689611, Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy-, N~4~-[6-(methyloxy)quinolin-8-yl]pentane-1,4-diamine, SCHEMBL29409423, BDBM71542, KBio1_000806, KBio2_001310, KBio2_003878, KBio2_006446, KBio3_001723, NINDS_000806, GLXC-07787, HMS2090J17, BBL011330, EBC-26352, HY-12651A, STL146416, 1, N4-(6-methoxy-8-quinolinyl)-, AKOS005721199, DB01087, FA42456, WLN: T66 BNJ HO1 JMY1&3Z, IDI1_000806, SMP1_000263, NCGC00178754-01, NCGC00178754-02, NCGC00178754-03, AC-23007, AS-30679, NCI60_001035, NCI60_005887, SY030293, SBI-0051491.P003, AB00053529, CS-0013754, NS00000469, C07627, D08420, EN300-144245, AB00053529-11, AB00053529_12, AB00053529_14, 4-amino-1-methylbutyl(6-methoxy-8-quinolyl)amine, F079201, Q419834, BRD-A55913614-316-06-2, BRD-A55913614-316-08-8, BRD-A55913614-316-09-6, SR-05000001864-11, N4-(6-Methoxyquinolin-8-yl)pentane-1,4-diamine (2 H3PO4), N4-(6-methoxy-8-quinolinyl)pentane-1,4-diamine;phosphoric acid, N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid, (4-amino-1-methyl-butyl)-(6-methoxy-8-quinolyl)amine;phosphoric acid, 8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline; 4-N-(6-Methoxyquinolin-8-yl)pentane-1,4-diamine
Theoretical properties:
molecular_formula: C15H21N3O
molecular_weight: 259.35 g/mol
exact_mass: 259.168462302 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 6
heavy_atom_count: 19
topological_polar_surface_area: 60.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Viscous liquid
color: Viscous liquid
melting_point: < 25 °C
solubility: 5.64e-02 g/L
Descriptions:
pubchem: Primaquine is 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. It has a role as an antimalarial. It is an aromatic ether, an aminoquinoline and a N-substituted diamine.
chebi: An <em>N</em>-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N<small><sup>4</small></sup> position. It is a drug used in the treatment of malaria and <em>Pneumocystis</em> pneumonia.
chembl: PRIMAQUINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Primaquine is a medication used to treat and prevent malaria and to treat Pneumocystis pneumonia. Specifically it is used for malaria due to Plasmodium vivax and Plasmodium ovale along with other medications and for prevention if other options cannot be used. It is an alternative treatment for Pneumocystis pneumonia together with clindamycin. It is taken by mouth.
Common side effects include nausea, vomiting, and stomach cramps. Primaquine should not be given to people with glucose-6-phosphate dehydrogenase (G6PD) deficiency due to the risk of red blood cell breakdown. It is often recommended that primaquine not be used during pregnancy. It may be used while breastfeeding if the baby is known not to have G6PD deficiency. The mechanisms of action are not entirely clear but are believed to involve effects on the malaria parasites' DNA.
Primaquine was first made in 1946. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.