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Primaquine diphosphate

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Name

Primaquine diphosphate

EINECS 200-560-8
CAS No. 63-45-6 Density N/A
PSA 235.31000 LogP 1.69880
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 Molecular Structure of 63-45-6 (Primaquine diphosphate) Hazard Symbols ToxicT
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);

Article Data 2

Primaquine diphosphate Synthetic route

90-34-6

Primaquine

63-45-6

primaquine diphosphate

Conditions
ConditionsYield
With phosphoric acid In diethyl ether Darkness;
96-96-8

4-methoxy-2-nitroaniline

63-45-6

primaquine diphosphate

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

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 NOx and POx. 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) Effect 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.

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