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| CAS No.: | 71963-77-4 |
|---|---|
| Name: | Artemether |
| Article Data: | 13 |
| Molecular Structure: | |
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| 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 |
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| Conditions | Yield |
|---|---|
| With perchloric acid In ethanol at 0℃; for 8h; pH=2; Reagent/catalyst; pH-value; Temperature; | 97.6% |
| Conditions | Yield |
|---|---|
| With sulfuric acid In isopropyl alcohol at 0 - 12℃; for 4h; pH=2; Solvent; Temperature; Reagent/catalyst; pH-value; | 97.2% |
| 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; |
| Conditions | Yield |
|---|---|
| With dimethylphosphoric acid; boron trifluoride diethyl etherate at 3 - 20℃; Reagent/catalyst; Temperature; | 96.2% |
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With boron trifluoride diethyl etherate In diethyl ether for 24h; Ambient temperature; | A n/a B n/a C 56% |
| 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; |
| 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; |
| 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; |
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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.