Primaquine diphosphate supplier

Name
Primaquine diphosphate
EINECS 200-560-8
CAS No. 63-45-6
Article Data2
CAS DataBase
Density
Solubility moderately soluble in water
Melting Point 199-205 °C
Formula C₁₅H₂₁N₃O^.2(H₃PO₄)
Boiling Point 451.1 °C at 760 mmHg
Molecular Weight 455.342
Flash Point 226.6 °C
Transport Information UN 2811 6.1/PG 3
Appearance orange powder
Safety 45
Risk Codes 25
Molecular Structure
Hazard Symbols T
Synonyms Prestwick_406;[(4S)-4-[(6-methoxyquinolin-8-yl)amino]pentyl]azanium;Primaquine phosphate (USP);Quinoline, 8-[ (4-amino-1-methylbutyl)amino]-6-methoxy-, phosphate (1:2);Primaquine (TN);N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine; phosphoric acid;1,4-Pentanediamine, N4- (6-methoxy-8-quinolinyl)-, phosphate (1:2);primaquine bis(phosphate);
PSA 235.31000
LogP 1.69880

Synthetic route

: 90-34-6
Primaquine

: 63-45-6
primaquine diphosphate

Conditions

Conditions	Yield
With phosphoric acid In diethyl ether Darkness;

: 96-96-8
4-methoxy-2-nitroaniline

: 63-45-6
primaquine diphosphate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: arsenic(V) oxide; phosphoric acid / 1 h / 100 °C / Darkness 2: hydrogen / 2585.81 Torr / Darkness 3: triethylamine / 6 h / 150 °C / Darkness 4: hydrazine / ethanol / 72 h / Reflux; Darkness 5: phosphoric acid / diethyl ether / Darkness View Scheme

: 85-81-4
6-methoxy-8-nitroquinoline

: 63-45-6
primaquine diphosphate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogen / 2585.81 Torr / Darkness 2: triethylamine / 6 h / 150 °C / Darkness 3: hydrazine / ethanol / 72 h / Reflux; Darkness 4: phosphoric acid / diethyl ether / Darkness View Scheme

: 90-52-8
6-methoxyquinolin-8-amine

: 63-45-6
primaquine diphosphate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / 6 h / 150 °C / Darkness 2: hydrazine / ethanol / 72 h / Reflux; Darkness 3: phosphoric acid / diethyl ether / Darkness View Scheme

: 83532-78-9
N-phthalolylprimaquine

: 63-45-6
primaquine diphosphate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine / ethanol / 72 h / Reflux; Darkness 2: phosphoric acid / diethyl ether / Darkness View Scheme

: 2389-60-8
Z-Lys(Boc)-OH

: 63-45-6
primaquine diphosphate

: 4'-N-(Nε-boc-N-Cbz-lysyl)primaquine

Conditions

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide 1.) 0 deg C, 4 h, 2.) RT, overnight;	95%

: 108381-23-3
2-chloro-4,6-dimethylpyrimidine-5-carboxylic acid ethyl ester

: 63-45-6
primaquine diphosphate

: ethyl 2-(4-(6-methoxyquinolin-8-ylamino)pentylamino)-4,6-dimethylpyrimidin-5-carboxylate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	95%

: 63-45-6
primaquine diphosphate

: 1318851-87-4
C15H19(2)H2N3O

Conditions

Conditions	Yield
With sulfuric acid; water-d2 at 95℃; for 8h; Temperature;	95%

: 36746-07-3
2-chloro-4-methyl-6-phenylpyrimidine-5-carboxylic acid ethyl ester

: 63-45-6
primaquine diphosphate

: ethyl 2-(4-(6-methoxyquinolin-8-ylamino)pentylamino)-6-methyl-4-phenylpyrimidin-5-carboxylate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	94%

: 63-45-6
primaquine diphosphate

: 108-24-7
acetic anhydride

: 77229-67-5
N-acetyl-primaquine

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1h;	92%

: 1448992-15-1
isopropyl 2-chloro-4-methyl-6-phenylpyrimidine-5-carboxylate

: 63-45-6
primaquine diphosphate

: isopropyl 2-(4-(6-methoxyquinolin-8-ylamino)pentylamino)-6-methyl-4-phenylpyrimidin-5-carboxylate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	92%

: methyl 2-chloro-4,6-dimethylpyrimidine-5-carboxylate

: 63-45-6
primaquine diphosphate

: methyl 2-(4-(6-methoxyquinolin-8-ylamino)pentylamino)-4,6-dimethylpyrimidin-5-carboxylate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	92%

: 1448992-18-4
2-chloro-4-(4-fluorophenyl)-6-methylpyrimidine-5-carboxylic acid ethyl ester

: 63-45-6
primaquine diphosphate

: ethyl 4-(4-fluorophenyl)-2-(4-(6-methoxyquinolin-8-ylamino)pentylamino)-6-methylpyrimidin-5-carboxylate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	91%

: 1376766-60-7
C15H14ClN3O4

: 63-45-6
primaquine diphosphate

: isopropyl 2-(4-(6-methoxyquinolin-8-ylamino)pentylamino)-6-methyl-4-(4-nitrophenyl)pyrimidin-5-carboxylate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	91%

: 24424-99-5
di-tert-butyl dicarbonate

: 63-45-6
primaquine diphosphate

: tert-butyl (4-((6-methoxyquinolin-8-yl)amino)pentyl)carbamate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 25℃;	91%

: Ethyl 2-chloro-4-(4-methoxyphenyl)-6-methylpyrimidine-5-carboxylate

: 63-45-6
primaquine diphosphate

: Ethyl 2-(4-(6-methoxyquinolin-8-ylamino)pentylamino)-6-methyl-4-(4-methoxyphenyl)pyrimidin-5-carboxylate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	90%

: 2892-62-8
3,4-dibutoxy-3-cyclobutene-1,2-dione

: 63-45-6
primaquine diphosphate

: 1487428-85-2
C34H40N6O4

Conditions

Conditions	Yield
Stage #1: primaquine diphosphate With triethylamine In methanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,4-dibutoxy-3-cyclobutene-1,2-dione In methanol for 48h; Inert atmosphere; Reflux;	89%

: 1376766-58-3
C15H14ClN3O4

: 63-45-6
primaquine diphosphate

: isopropyl 2-(4-(6-methoxyquinolin-8-ylamino)pentylamino)-6-methyl-4-(3-nitrophenyl)pyrimidin-5-carboxylate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	88%

: 2-[(1H-1,2,3-benzotriazole-1-carbonyl)amino]-N-(diphenylmethyl)-4-methylpentanamide

: 63-45-6
primaquine diphosphate

: N-(diphenylmethyl)-2-[({4-[(6-methoxyquinolin-8-yl)amino]pentyl}carbamoyl)-amino]-4-methylpentanamide

Conditions

Conditions	Yield
Stage #1: primaquine diphosphate With sodium hydroxide In water pH=9 - 10; Stage #2: 2-[(1H-1,2,3-benzotriazole-1-carbonyl)amino]-N-(diphenylmethyl)-4-methylpentanamide In 1,4-dioxane at 20℃; Darkness;	87%

: 63-45-6
primaquine diphosphate

: 90-34-6
Primaquine

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 2h; pH=10; Darkness;	86%
With water; sodium hydroxide Heating;	60%
Stage #1: primaquine diphosphate With triethylamine In dichloromethane for 0.5h; Cooling with ice; Stage #2: In 2,2'-iminobis[ethanol]

: 1376766-59-4
C15H14ClN3O4

: 63-45-6
primaquine diphosphate

: isopropyl 2-(4-(6-methoxyquinolin-8-ylamino)pentylamino)-6-methyl-4-(2-nitrophenyl)pyrimidin-5-carboxylate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	85%

: 2-[(1H-1,2,3-benzotriazole-1-carbonyl)amino]-N-[(4-chlorophenyl)(phenyl)methyl]-2-phenylacetamide

: 63-45-6
primaquine diphosphate

: N-[(4-chlorophenyl)(phenyl)methyl]-2-[({4-[(6-methoxyquinolin-8-yl)amino]pentyl}carbamoyl)amino]-2-phenylacetamide

Conditions

Conditions	Yield
Stage #1: primaquine diphosphate With sodium hydroxide In water pH=9 - 10; Stage #2: 2-[(1H-1,2,3-benzotriazole-1-carbonyl)amino]-N-[(4-chlorophenyl)(phenyl)methyl]-2-phenylacetamide In 1,4-dioxane at 20℃; Darkness;	85%

: 1042740-40-8
(N-(4-((6-methoxyquinolin-8-yl)amino)pentyl)-1H-benzo[d][1,2,3]triazole-1-carboxamide)

: 63-45-6
primaquine diphosphate

: 1267807-38-4
1,3-bis(4-((6-methoxyquinolin-8-yl)amino)pentyl)urea

Conditions

Conditions	Yield
With sodium dithionite; triethylamine In dichloromethane at 65℃; Microwave irradiation; Darkness;	84%

: 2892-62-8
3,4-dibutoxy-3-cyclobutene-1,2-dione

: 63-45-6
primaquine diphosphate

: 1487428-84-1
C23H29N3O4

Conditions

Conditions	Yield
Stage #1: primaquine diphosphate With triethylamine In methanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,4-dibutoxy-3-cyclobutene-1,2-dione In methanol for 48h; Inert atmosphere; Reflux;	82%

: 63-45-6
primaquine diphosphate

: 108-94-1
cyclohexanone

: 68-11-1
mercaptoacetic acid

: 1356475-81-4
4-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}-1-thia-4-azaspiro[4.5]decan-3-one

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene at 110℃; for 3h;	80%

...Expand

: 63-45-6
primaquine diphosphate

: 5222-73-1
3,4-dimethoxy-3-cyclobutene-1,2-dione

: 3-methoxy-4-({4-[(6-methoxyquinolin-8-yl)amino]pentyl}amino)cyclobut-3-ene-1,2-dione

Conditions

Conditions	Yield
Stage #1: primaquine diphosphate With triethylamine In methanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,4-dimethoxy-3-cyclobutene-1,2-dione In methanol for 12h; Inert atmosphere; Reflux;	79%

: 505-48-6
octane-1,8-dioic acid

: 63-45-6
primaquine diphosphate

: N,N’-bis({4-[(6-methoxyquinolin-8-yl)amino]pentyl})octanediamide

Conditions

Conditions	Yield
Stage #1: primaquine diphosphate With triethylamine In dichloromethane Stage #2: octane-1,8-dioic acid With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 24h;	78%

: 110-15-6
succinic acid

: 63-45-6
primaquine diphosphate

: N,N'-bis({4-[(6-methoxyquinolin-8-yl)amino]pentyl})butanediamide

Conditions

Conditions	Yield
Stage #1: primaquine diphosphate With triethylamine In dichloromethane Stage #2: succinic acid With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 24h;	77%

: C35H44N6O13

: 63-45-6
primaquine diphosphate

: C44H60N8O11

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide	76%

: 110-94-1
1,5-pentanedioic acid

: 63-45-6
primaquine diphosphate

: N,N’-bis({4-[(6-methoxyquinolin-8-yl)amino]pentyl})pentanediamide

Conditions

Conditions	Yield
Stage #1: primaquine diphosphate With triethylamine In dichloromethane Stage #2: 1,5-pentanedioic acid With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 24h;	73%

: 63-45-6
primaquine diphosphate

: p-[(10-dihydroartemisininoxy)methyl]benzoic acid

: 1519728-36-9
C38H49N3O7

Conditions

Conditions	Yield
Stage #1: p-[(10-dihydroartemisininoxy)methyl]benzoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In dichloromethane at 0℃; for 1h; Stage #2: primaquine diphosphate With triethylamine In dichloromethane at 0 - 20℃;	72%

: 63-45-6
primaquine diphosphate

: 8-amino-6-hydroxyquinoline dihydrobromide

Conditions

Conditions	Yield
With hydrogen bromide for 48h; Heating;	71%

: 2-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-N-(4-((6-methoxyquinolin-8-yl)amino)pentyl)hydrazinecarboxamide

: 63-45-6
primaquine diphosphate

: N,N-bis(4-((6-methoxyquinolin-8-yl)amino)pentyl)hydrazine-1,2-dicarboxamide

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane; diethyl ether	68%

: dispiro[adamantane-2,2'-[1,3,5]trioxolane-4',1"-cyclohexane]-3"-yl 4-nitrophenylcarbonate

: 63-45-6
primaquine diphosphate

: dispiro[adamantane-2,2'-[1,3,5]trioxolane-4',1"-cyclohexane]-3"-yl N-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}carbamate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;	68%

: 2-[(1H-1,2,3-benzotriazole-1-carbonyl)amino]-N-(4-bromophenyl)-2-(4-chlorophenyl)acetamide

: 63-45-6
primaquine diphosphate

: N-(4-bromophenyl)-2-(4-chlorophenyl)-2-[({4-[(6-methoxyquinolin-8-yl)amino]pentyl}carbamoyl)amino]acetamide

Conditions

Conditions	Yield
Stage #1: primaquine diphosphate With sodium hydroxide In water pH=9 - 10; Stage #2: 2-[(1H-1,2,3-benzotriazole-1-carbonyl)amino]-N-(4-bromophenyl)-2-(4-chlorophenyl)acetamide In 1,4-dioxane at 20℃; Darkness;	67%

Primaquine diphosphate Specification

The IUPAC name of Primaquine phosphate is 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine; phosphoric acid. With the CAS registry number 63-45-6 and EINECS 200-560-8, it is also named as (+-)-8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline phosphate (1:2). The classification codes are Antimalarial; Drug / Therapeutic Agent; Mutation data; Reproductive Effect. It is orange powder which is is highly toxic and flammable. When heated to decomposition it emits toxic fumes of NO_x and PO_x. So the storage environment should be well-ventilated, low-temperature and dry.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.6; (4)ACD/LogD (pH 7.4): -1.19; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 28.6 Å²; (13)Enthalpy of Vaporization: 71.01 kJ/mol; (14)Vapour Pressure: 2.5E-08 mmHg at 25°C; (15)Rotatable Bond Count: 6; (16)Exact Mass: 455.122253; (17)MonoIsotopic Mass: 455.122253; (18)Topological Polar Surface Area: 216; (19)Heavy Atom Count: 29; (20)Complexity: 312.

Uses of Primaquine phosphate: It is an aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It can also be used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. The adverse effects include anemias and GI disturbances.

When you are using this chemical, please be cautious about it as the following:
It is toxic if swallowed. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. SMILES:O=P(O)(O)O.O=P(O)(O)O.O(c1cc(NC(C)CCCN)c2ncccc2c1)C
2. InChI:InChI=1/C15H21N3O.2H3O4P/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14;2*1-5(2,3)4/h4,6,8-11,18H,3,5,7,16H2,1-2H3;2*(H3,1,2,3,4)
3. InChIKey:GJOHLWZHWQUKAU-UHFFFAOYAE

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
bird - domestic	LD50	intravenous	19300ug/kg (19.3mg/kg)	Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1775, 1970.
mouse	LD50	intraperitoneal	105mg/kg (105mg/kg)	Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1775, 1970.
mouse	LD50	oral	68mg/kg (68mg/kg)	Transactions of the Royal Society of Tropical Medicine and Hygiene. Vol. 74, Pg. 43, 1980.
rat	LD50	oral	177mg/kg (177mg/kg)	Journal of Medicinal Chemistry. Vol. 32, Pg. 1728, 1989.

Product Name

Primaquine diphosphate

Synthetic route

Primaquine diphosphate Specification

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