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Basic Information

Molecular Structure:
CAS No.:	71963-77-4
Name:	Artemether
Article Data:	13

Formula:	C₁₆H₂₆O₅
Molecular Weight:	298.379
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%;
EINECS:	663-549-0
Density:	1.18 g/cm³
Melting Point:	86-89oC
Boiling Point:	357.5 °C at 760 mmHg
Flash Point:	140.5 °C
Hazard Symbols:	Xn
Risk Codes:	22
Safety:	24/25
Transport Information:	OTH
PSA:	46.15000
LogP:	2.84080

Synthetic route

: 1445-45-0
Trimethyl orthoacetate

: 71939-50-9
dihydroartemisinin

: 71963-77-4
artemether

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether for 24h; Ambient temperature;	A n/a B n/a C 70%

...Expand

: 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

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

...Expand

: 67-56-1
methanol

: 71939-50-9
dihydroartemisinin

A: 71963-77-4
artemether

B: α-artemether

Conditions

Conditions	Yield
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;

...Expand

: 116-11-0
2-Methoxypropene

: 81496-81-3
dihydroartesiminin

: 71963-77-4
artemether

Conditions

Conditions	Yield
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

Conditions	Yield
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;

Raw Materials

116-11-0

77-76-9

149-73-5

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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.