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Artemether

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Name

Artemether

EINECS 663-549-0
CAS No. 71963-77-4 Density 1.18 g/cm3
PSA 46.15000 LogP 2.84080
Solubility Melting Point 86-89oC
Formula C16H26O5 Boiling Point 357.5 °C at 760 mmHg
Molecular Weight 298.38 . Flash Point 140.5 °C
Transport Information OTH Appearance
Safety 24/25 Risk Codes 22
Molecular Structure Molecular Structure of 71963-77-4 (Artemether) Hazard Symbols Xn
Synonyms

Albendazole Oral Suspension;SM 224;Artemetero [INN-Spanish];beta-Dihydroartemisinin methyl ether;Artemether [INN];3,12-Epoxy-12H-pyrano[4,3-j]-1,2- benzodioxepin,decahydro-10-methoxy-3,6,9- trimethyl-,(3R,5aS,6R,8aS,9R,10S,12R,12aR)-;Coartem;Methyl-dihydroartemisinine;Artemetherum [INN-Latin];3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin, decahydro-10-methoxy-3,6,9-trimethyl-;beta-Artemether;Methyl-ether-qinghaosu;[3R-(3.alpha.,5a.beta.,6.beta.,8a.beta.,9.alpha.,10.alpha.,12.beta.,12aR*)]-Decahydro-10-methoxy-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4.3-j]-1,2-benzodioxepin;Artemisininelactol methyl ether;Artemisinin ,Artemether99%;

 

Artemether Synthetic route

1445-45-0

Trimethyl orthoacetate

71939-50-9

dihydroartemisinin

71963-77-4

artemether

Conditions
ConditionsYield
With perchloric acid In ethanol at 0℃; for 8h; pH=2; Reagent/catalyst; pH-value; Temperature;97.6%
24823-81-2

trimethoxypropane

71939-50-9

dihydroartemisinin

71963-77-4

artemether

Conditions
ConditionsYield
With sulfuric acid In isopropyl alcohol at 0 - 12℃; for 4h; pH=2; Solvent; Temperature; Reagent/catalyst; pH-value;97.2%
71939-50-9

dihydroartemisinin

149-73-5

trimethyl orthoformate

71963-77-4

artemether

Conditions
ConditionsYield
With methanesulfonic acid In ethanol at 5 - 20℃; for 3h; pH=5; Solvent; pH-value; Temperature; Reagent/catalyst;96.6%
toluene-4-sulfonic acid In methanol at 30℃; for 0.5h;
67-56-1

methanol

81496-81-3

dihydroartesiminin

71963-77-4

artemether

Conditions
ConditionsYield
With dimethylphosphoric acid; boron trifluoride diethyl etherate at 3 - 20℃; Reagent/catalyst; Temperature;96.2%
81496-81-3

dihydroartesiminin

149-73-5

trimethyl orthoformate

71963-77-4

artemether

Conditions
ConditionsYield
Stage #1: dihydroartesiminin; trimethyl orthoformate In methanol at 20℃; for 0.25h;
Stage #2: With acetyl chloride In methanol at 10 - 15℃;
Stage #3: With sodium hydrogencarbonate In methanol; water at 0 - 5℃; for 2h; Product distribution / selectivity;
74.67%
3976-69-0

Methyl (R)-3-hydroxybutyrate

71939-50-9

dihydroartemisinin

A

82596-30-3

9,10-dehydrodihydroartemisinin

B

71963-77-4

artemether

C

120020-67-9

C20H32O7

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In diethyl ether for 24h; Ambient temperature;A n/a
B n/a
C 70%
53562-86-0

(S)-3-hydroxybutyric acid methyl ester

71939-50-9

dihydroartemisinin

A

82596-30-3

9,10-dehydrodihydroartemisinin

B

71963-77-4

artemether

C

119946-74-6

C20H32O7

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In diethyl ether for 24h; Ambient temperature;A n/a
B n/a
C 56%
67-56-1

methanol

71939-50-9

dihydroartemisinin

A

71963-77-4

artemether

B

α-artemether

Conditions
ConditionsYield
In benzene at 20℃; for 24h; Product distribution; Further Variations:; Reaction partners; Solvents; reaction times;
With hydrogenchloride In acetic acid methyl ester; water at 20 - 23℃; for 4.5h; Temperature; Concentration; Solvent;
116-11-0

2-Methoxypropene

81496-81-3

dihydroartesiminin

71963-77-4

artemether

Conditions
ConditionsYield
Stage #1: 2-Methoxypropene; dihydroartesiminin In methanol at 20℃; for 0.25h;
Stage #2: With methanesulfonyl chloride In methanol at 10 - 20℃;
Stage #3: With sodium hydrogencarbonate In methanol at 20℃; for 2h; Product distribution / selectivity;
77-76-9

2,2-dimethoxy-propane

81496-81-3

dihydroartesiminin

71963-77-4

artemether

Conditions
ConditionsYield
Stage #1: 2,2-dimethoxy-propane; dihydroartesiminin In methanol at 20℃; for 0.25h;
Stage #2: With chloro-trimethyl-silane In methanol at 10 - 20℃;
Stage #3: With sodium hydrogencarbonate In methanol at 20℃; for 2h; Product distribution / selectivity;
1445-45-0

Trimethyl orthoacetate

81496-81-3

dihydroartesiminin

71963-77-4

artemether

Conditions
ConditionsYield
Stage #1: Trimethyl orthoacetate; dihydroartesiminin With sulfuric acid In methanol
Stage #2: With sulfuric acid In methanol
Stage #3: With sodium hydrogencarbonate In methanol; water Product distribution / selectivity;
With boron trifluoride diethyl etherate In methanol at 10 - 20℃; for 4h;98 g

α-artemether

71963-77-4

artemether

Conditions
ConditionsYield
With chloro-trimethyl-silane In toluene at 25 - 30℃; for 12h;
67-56-1

methanol

81496-81-3

dihydroartesiminin

A

71963-77-4

artemether

B

α-artemether

Conditions
ConditionsYield
Stage #1: dihydroartesiminin With dodecatungstophosphoric acid hydrate In dichloromethane at 20℃; for 0.0833333h;
Stage #2: methanol In dichloromethane at 20℃; for 3h; optical yield given as %de;
63968-64-9

C12H13O2(CH3)3(O)(OO)

A

71963-77-4

artemether

B

α-artemether

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate / methanol
2.1: dodecatungstophosphoric acid hydrate / dichloromethane / 0.08 h / 20 °C
2.2: 3 h / 20 °C
View Scheme
67-56-1

methanol

63968-64-9

C12H13O2(CH3)3(O)(OO)

A

71963-77-4

artemether

B

α-artemether

Conditions
ConditionsYield
With sodium tetrahydroborate; cellulose sulfuric acid; trimethyl orthoformate In tetrahydrofuran at -5 - 20℃; for 2.5h;A n/a
B n/a
67-56-1

methanol

71939-50-9

dihydroartemisinin

71963-77-4

artemether

Conditions
ConditionsYield
With amberlyst-15 In 2-methyltetrahydrofuran at 20℃; for 4h; Kinetics; Reagent/catalyst; Temperature; Flow reactor;
67-56-1

methanol

71939-50-9

dihydroartemisinin

71963-77-4

artemether

Conditions
ConditionsYield
With perchloric acid In dichloromethane at 30 - 38℃; for 0.166667h; Temperature; Large scale;756 g
1445-45-0

Trimethyl orthoacetate

63968-64-9

C12H13O2(CH3)3(O)(OO)

71963-77-4

artemether

Conditions
ConditionsYield
Stage #1: C12H13O2(CH3)3(O)(OO) With methanol; sodium tetrahydroborate at -10 - -5℃; for 3h;
Stage #2: Trimethyl orthoacetate With sulfuric acid; boron trifluoride diethyl etherate In methanol at 20℃; for 4h; pH=6 - 8; Catalytic behavior; Temperature;
101.9 g
71963-77-4

artemether

deoxy-β-artemether

Conditions
ConditionsYield
With zinc In acetic acid for 1h; Ambient temperature;72%
71963-77-4

artemether

A

9α-acetoxy-10β-methoxyartemethin-I

B

3α-hydroxydeoxydihydroqinghaosu

C

3α-hydroxy-12β-methoxyartemethin-III

Conditions
ConditionsYield
With iron(II) sulfate In water; acetonitrile at 37℃;A 37%
B 4%
C 44%
10318-18-0

DL-cysteine hydrochloride

71963-77-4

artemether

A

9α-acetoxy-10β-methoxyartemethin-I

B

3α-hydroxy-12β-methoxyartemethin-III

C

Acetic acid (1R,3S,4R,4aS,7R,8S,8aR)-8-ethyl-8a-hydroxy-3-methoxy-4,7-dimethyl-octahydro-isochromen-1-yl ester

D

3-[2-((1R,3S,4R,4aS,7R,8S,8aR)-1-Acetoxy-8a-hydroxy-3-methoxy-4,7-dimethyl-octahydro-isochromen-8-yl)-ethylsulfanyl]-2-amino-propionic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate; iron(II) sulfate In acetonitrile at 20℃; for 4h; Further byproducts given;A 26%
B 44%
C 10%
D 3.2%
71963-77-4

artemether

1,4-diacetylbenzene bis(trimethylsilyl) enol ether

10-m-acetylphenylartemisinin dimer

Conditions
ConditionsYield
Stage #1: artemether With titanium tetrachloride In dichloromethane at -78℃; for 0.0833333h; Metallation;
Stage #2: 1,4-diacetylbenzene bis(trimethylsilyl) enol ether In dichloromethane at -78℃; for 1h; Condensation;
33%
71963-77-4

artemether

A

3α-hydroxydeoxy-β-artemether

B

2-[(R)-4-Methyl-2-oxo-3-(3-oxo-butyl)-cyclohexyl]-propionaldehyde

C

9α-acetoxy-10β-methoxyartemethin-I

Conditions
ConditionsYield
With iron(II) chloride In acetonitrile for 0.0333333h; Ambient temperature;A 23%
B 16%
C 32%
71963-77-4

artemether

183060-22-2

1,4-diacetylbenzene bis(trimethylsilyl) enol ether

229981-82-2

10-p-acetylphenylartemisinin dimer

Conditions
ConditionsYield
Stage #1: artemether With titanium tetrachloride In dichloromethane at -78℃; for 0.0833333h; Metallation;
Stage #2: 1,4-diacetylbenzene bis(trimethylsilyl) enol ether In dichloromethane at -78℃; for 1h; Condensation;
26%
10318-18-0

DL-cysteine hydrochloride

71963-77-4

artemether

C18H29NO6S

Conditions
ConditionsYield
With sodium hydrogencarbonate; iron(II) sulfate In acetonitrile at 20℃; for 4h;1.4%
32195-55-4

Mn(TPP)Cl

71963-77-4

artemether

Acetic acid (1R,3S,4R,4aS,7R,8S,8aR)-8a-hydroxy-3-methoxy-4,7-dimethyl-8-[2-((4Z,10Z,15Z,19Z)-(S)-5,10,15,20-tetraphenyl-2,3,22,24-tetrahydro-porphin-2-yl)-ethyl]-octahydro-isochromen-1-yl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium borohydride; cadmium(II) nitrate 1.) CH2Cl2, r.t., 1 h, 2.) CH2Cl2, DMF, 30 min; Yield given. Multistep reaction;
71963-77-4

artemether

A

1356857-18-5

β-2-deoxy-9-epidihydroartemisinin

B

107466-88-6

(2S, 3R, 6S)-2-(3-oxobutyl)-3-methyl-6-<(R)2-propanal>-cyclohexanone

C

72807-92-2

deoxydihydroqinghaosu

Conditions
ConditionsYield
With 1-Benzyl-1,4-dihydronicotinamide; lumiflavin In acetonitrile at 20℃; for 2.5h; pH=7.4; aq. phosphate buffer; Inert atmosphere;
71963-77-4

artemether

A

1356857-18-5

β-2-deoxy-9-epidihydroartemisinin

B

72807-92-2

deoxydihydroqinghaosu

Conditions
ConditionsYield
With 1-Benzyl-1,4-dihydronicotinamide; riboflavin In acetonitrile at 20℃; for 3h; pH=7.4; aq. phosphate buffer; Inert atmosphere;A 52 %Spectr.
B 12 %Spectr.
71963-77-4

artemether

A

9α-acetoxy-10β-methoxyartemethin-I

B

3α-hydroxy-12β-methoxyartemethin-III

Conditions
ConditionsYield
With oxygen; methylene blue; ascorbic acid In acetonitrile at 20℃; for 24h; pH=7.4; aq. phosphate buffer;

Artemether Specification

1. Introduction of Artemether

Artemether is one kind of white crystals or a white, crystalline powder. The chemical name of Artemether is (3R,5aS,6R,8aS,9R,10S,12R,12aR)-Decahydro-10-methoxy-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin. The Product Categories of this chemical is Antimalarial. Artemether is toxic. It is flammable. It will produce Stimulate smoke when buring. So the storage environment should be ventilate, low-temperature and dry.

2. Properties of Artemether

Physical properties about Artemether are:
(1)Boiling Point: 358 °C; (2)Flash Point: 141 °C; (3)Density: 1.18 g/cm3; (4)Index of Refraction: 1.518; (5)Molar Refractivity: 76.54 cm3; (6)Molar Volume: 252.5 cm3; (7)Surface Tension: 39.9 dyne/cm; (8)XLogP3-AA: 3.1; (9)H-Bond Acceptor: 5; (10)Rotatable Bond Count: 1; (11)Exact Mass: 298.178024; (12)MonoIsotopic Mass: 298.178024; (13)Topological Polar Surface Area: 46.2; (14)Heavy Atom Count: 21.

3. Structure Descriptors of Artemether

(1) Canonical SMILES: CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)OC)C;
(2) Isomeric SMILES: C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)OC)C;
(3) InChI: InChI=1S/C16H26O5/c1-9-5-6-12-10(2)13(17-4)18-14-16(12)11(9)7-8-15(3,19-14)20-21-16/h9-14H,5-8H2,1-4H3/t9-,10-,11+,12+,13+,14-,15-,16-/m1/s1;
(4) InChIKey: SXYIRMFQILZOAM-HVNFFKDJSA-N.

4. Toxicity of Artemether

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 263mg/kg (263mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. 2, Pg. 138, 1981.
mouse LD50 oral 1gm/kg (1000mg/kg)   Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. D13, Pg. 280, 1992.
mouse LD50 subcutaneous 390mg/kg (390mg/kg)   Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. D13, Pg. 280, 1992.

5. Safety information of Artemether

Poison by intramuscular route. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.

6. Uses of Artemether

Artemether is an antimalarial used for the treatment of multi-drug resistant strains of falciparum malaria. Arteether is the derivative of artemisinin, it is a strong schizonticide and can take rapid control of symptoms by killing plasmodium, it is much more effective than artemisinin and used for the curative treatment of all kinds of malaria, especially for the cerebal malaria , severe malaria and chloroquine-resistant malaria. It is also applied in combination with lumefantrine in clinical treatments of malaria.

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