Primaquine

Details

• Internal ID: 78c75431-f980-4e6e-b49a-cbd2c53e86e9
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Aminoquinolines and derivatives
• IUPAC Name: 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
• SMILES (Canonical): CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2
• SMILES (Isomeric): CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2
• 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
• InChI Key: INDBQLZJXZLFIT-UHFFFAOYSA-N
• Popularity: 4,954 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₁N₃O
• Molecular Weight: 259.35 g/mol
• Exact Mass: 259.168462302 g/mol
• Topological Polar Surface Area (TPSA): 60.20 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 90-34-6
• Primachin
• Neo-Quipenyl
• 8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline
• Primaquin
• Primachinum
• Primaquinum
• Primaquina
• Kanaprim
• Primachina
• (+/-)-Primaquine
• 1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)-
• Maliride
• SN 13,272
• 6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline
• Primaquinum [INN-Latin]
• Primaquina [INN-Spanish]
• 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
• N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine
• NSC 27296
• CCRIS 4109
• CHEBI:8405
• S. N. 13272
• HSDB 6516
• 8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline
• EINECS 201-987-2
• UNII-MVR3634GX1
• NSC-27296
• Primaquine (INN)
• WR 2975
• MVR3634GX1
• N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine
• Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy
• WR-2975
• SN-13272
• DTXSID8023509
• N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
• (+)-Primaquine
• (-)-Primaquine
• NSC27296
• N(4)-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
• 1,4-Pentanediamine, N(4)-(6-methoxy-8-quinolinyl)-
• 8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline
• Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy-
• N-[(S)-4-Amino-1-methylbutyl]-6-methoxy-8-quinolinamine
• Quinoline, 8-((4-amino-1-methylbutyl)amino)-6-methoxy-
• Primachina [DCIT]
• dl-Primaquine
• PRIMAQUINE [INN]
• Primaquinum (INN-Latin)
• Primaquina (INN-Spanish)
• Primaquine [INN:BAN]
• BRN 0019337
• Maliride; NSC 27296; Neo-Quipenyl; Primachin
• N4-(6-methoxy-8-quinolyl)pentane-1,4-diamine
• 6-Methoxy-8-[(4-amino-1-methylbutyl)amino]quinoline
• N~4~-[6-(methyloxy)quinolin-8-yl]pentane-1,4-diamine
• CHEMBL506
• MLS001334045
• Kanaprim (TN)
• n4-[6-methoxy-8-quinolinyl]-1,4-pentanediamine
• 4-22-00-05817 (Beilstein Handbook Reference)
• NCGC00178754-06
• SMR000875314
• 6-Methoxy-8-((4-amino-1-methylbutyl)amino)quinoline
• Quinoline, 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-
• (RS)-primaquine
• TG1-296
• TG1-297
• 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
• SPBio_000674
• SPBio_002551
• (+)-N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine
• (-)-N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine
• BPBio1_000674
• cid_359247
• DTXCID903509
• GTPL9952
• BDBM71542
• KBio1_000806
• KBio2_001310
• KBio2_003878
• KBio2_006446
• KBio3_001723
• P01BA03
• NINDS_000806
• HMS2090J17
• BCP29271
• HY-12651A
• MFCD00598906
• 1, N4-(6-methoxy-8-quinolinyl)-
• AKOS005721199
• DB01087
• WLN: T66 BNJ HO1 JMY1&3Z
• IDI1_000806
• SMP1_000263
• NCGC00178754-01
• NCGC00178754-02
• NCGC00178754-03
• AC-23007
• AS-30679
• NCI60_001035
• NCI60_005887
• SBI-0051491.P003
• AB00053529
• CS-0013754
• FT-0687514
• C07627
• D08420
• EN300-144245
• AB00053529-11
• AB00053529_12
• AB00053529_14
• N-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine
• 4-amino-1-methylbutyl(6-methoxy-8-quinolyl)amine
• A843518
• N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
• Q419834
• BRD-A55913614-316-06-2
• SR-05000001864-11
• N4-(6-methoxy-8-quinolyl)pentane-1,4-diamine;Primaquine
• 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
• 57152-47-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9884	98.84%
Caco-2	+	0.6681	66.81%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.8286	82.86%
Subcellular localzation	Nucleus	0.6635	66.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9605	96.05%
OATP1B3 inhibitior	+	0.9467	94.67%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.8250	82.50%
BSEP inhibitior	+	0.8256	82.56%
P-glycoprotein inhibitior	-	0.9252	92.52%
P-glycoprotein substrate	+	0.7846	78.46%
CYP3A4 substrate	-	0.5334	53.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5523	55.23%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9300	93.00%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.6498	64.98%
CYP inhibitory promiscuity	-	0.5057	50.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6116	61.16%
Eye corrosion	-	0.9795	97.95%
Eye irritation	-	0.9736	97.36%
Skin irritation	-	0.7063	70.63%
Skin corrosion	-	0.8424	84.24%
Ames mutagenesis	+	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8048	80.48%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.7335	73.35%
skin sensitisation	-	0.8718	87.18%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6298	62.98%
Acute Oral Toxicity (c)	III	0.7007	70.07%
Estrogen receptor binding	+	0.6380	63.80%
Androgen receptor binding	+	0.5656	56.56%
Thyroid receptor binding	+	0.6595	65.95%
Glucocorticoid receptor binding	-	0.5680	56.80%
Aromatase binding	+	0.5359	53.59%
PPAR gamma	-	0.5740	57.40%
Honey bee toxicity	-	0.9590	95.90%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	-	0.6704	67.04%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2439	P05164	Myeloperoxidase	300 nM	IC50	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	8.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.66%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.64%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.20%	96.00%
CHEMBL288	Q08499	Phosphodiesterase 4D	94.97%	97.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.74%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.38%	99.17%
CHEMBL2581	P07339	Cathepsin D	91.21%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.68%	85.14%
CHEMBL2535	P11166	Glucose transporter	90.27%	98.75%
CHEMBL2243	O00519	Anandamide amidohydrolase	90.00%	97.53%
CHEMBL4581	P52732	Kinesin-like protein 1	89.97%	93.18%
CHEMBL2885	P07451	Carbonic anhydrase III	88.62%	87.45%
CHEMBL3401	O75469	Pregnane X receptor	88.26%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.98%	86.33%
CHEMBL3492	P49721	Proteasome Macropain subunit	87.17%	90.24%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.92%	94.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	85.31%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.64%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	84.53%	95.93%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.19%	82.69%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.00%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.00%	95.56%
CHEMBL3902	P09211	Glutathione S-transferase Pi	83.71%	93.81%
CHEMBL230	P35354	Cyclooxygenase-2	83.43%	89.63%
CHEMBL3891	P07384	Calpain 1	80.40%	93.04%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 4908
• LOTUS: LTS0177000
• wikiData: Q419834