Primaquine

Names

[ CAS No. ]:
90-34-6

[ Name ]:
Primaquine

[Synonym ]:
(±)-Primaquine
[14C]-Primaquine
1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)- (9CI)
Primaquine
4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
N4-(6-methoxy-8-quinolinyl)1,4-pentanediamine
Primaquin
Primachinum
1,4-Pentanediamine, N4- (6-methoxy-8-quinolinyl)-
N-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine
8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline
1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)-
Neo-Quipenyl
1,4-Pentanediamine, N(4)-(6-methoxy-8-quinolinyl)-
8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline
N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine
EINECS 201-987-2
Primaquinum
N-(6-Methoxyquinolin-8-yl)pentane-1,4-diamine
UNII:MVR3634GX1
Primachin
Primaquina
6-Methoxy-8-[(4-amino-1-methylbutyl)amino]quinoline
N'-(6-methoxy-8-quinolinyl)-1,4-pentanediamine
1,4-Pentanediamine, N-(6-methoxy-8-quinolinyl)-
N-[6-(methyloxy)quinolin-8-yl]pentane-1,4-diamine

Biological Activity

[Description]:

Primaquine is a potent antimalaria agent and a potent gametocytocide in falciparum malaria. Primaquine prevents relapse in vivax and ovale malaria[1][2].

[Related Catalog]:

Research Areas >> Infection

[References]

[1]. Baird JK, et al. Primaquine therapy for malaria. Clin Infect Dis. 2004 Nov 1;39(9):1336-45.

[2]. Ashley EA, et al. Primaquine: the risks and the benefits. Malar J. 2014 Nov 3;13:418.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
451.1±45.0 °C at 760 mmHg

[ Melting Point ]:
25°C

[ Molecular Formula ]:
C₁₅H₂₁N₃O

[ Molecular Weight ]:
259.347

[ Flash Point ]:
226.6±28.7 °C

[ Exact Mass ]:
259.168457

[ PSA ]:
60.17000

[ LogP ]:
2.67

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.616

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VA9650000

CHEMICAL NAME :: Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy-

CAS REGISTRY NUMBER :: 90-34-6

BEILSTEIN REFERENCE NO. :: 0019337

LAST UPDATED :: 199712

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C15-H21-N3-O

MOLECULAR WEIGHT :: 259.39

WISWESSER LINE NOTATION :: T66 BNJ HO1 JMY1&3Z

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15900 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 68800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 96 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 810 mg/kg/3W-I

TOXIC EFFECTS :: Behavioral - ataxia Liver - hepatitis (hepatocellular necrosis), zonal Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 283 mg/kg/5D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 336 mg/kg/16D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Gastrointestinal - hypermotility, diarrhea

MUTATION DATA

TEST SYSTEM :: Rodent - rat

DOSE/DURATION :: 8 mg/kg

REFERENCE :: SYXUD2 Shandong Yixueyuan Xuebao. Journal of Shandong Medical College. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) Beginning history not known. Volume(issue)/page/year: 23,26,1985

Safety Information

[ Hazard Codes ]:
Xn

[ HS Code ]:
2933499090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933499090

[ Summary ]:
2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%