Artemisinin

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Names

[ Name ]:
Artemisinin

[Synonym ]:
(3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3H)-one
(4S,5R,8S,9R,12S,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0.0]hexadecan-10-one
artemisininum
qinghausu
3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one, octahydro-3,6,9-trimethyl-, (5aS,6R,8aS,9R,12S,12aR)-
Artemisinin
UNII-9RMU91N5K2
ARTEANUIN
Quinghaosu
[3R-(3R,5aS,6S,8aS,9R,10R,12S,12aR**)]-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-one
3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one, octahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,12S,12aR)-
qinghaosu
QINGHAOSA
artemisinine
(+)-artemisinin
MFCD00081057
[3R-(3a,5ab,6b,8ab,9a,12b,12aR*)]-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one
qinghausau
ARTEMISINE
QHS
qinghosu
Arteannuin

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
389.9±42.0 °C at 760 mmHg

[ Melting Point ]:
156-157ºC

[ Molecular Formula ]:
C₁₅H₂₂O₅

[ Molecular Weight ]:
282.332

[ Flash Point ]:
172.0±27.9 °C

[ Exact Mass ]:
282.146729

[ PSA ]:
53.99000

[ LogP ]:
2.27

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.533

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KD4170000

CHEMICAL NAME :: 3,12-Epoxy-12H-pyranol(4,3-j)-1,2-benzodioxepin-10(3H )-one, octahydro-3,6,9-trimethyl-, (3- alpha,5a-beta,6-beta,8a-beta,9-alpha,12-beta,12aR*)-( +)-

CAS REGISTRY NUMBER :: 63968-64-9

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C15-H22-O5

MOLECULAR WEIGHT :: 282.37

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5576 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - tremor Behavioral - ataxia

REFERENCE :: JTCMEC Journal of Traditional Chinese Medicine (English Edition). (All-China Assoc. of Traditional Chinese Medicine, Academy of Traditional Chinese Medicine) V.1- 1981- Volume(issue)/page/year: 2,31,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2571 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - tremor Behavioral - ataxia

REFERENCE :: JTCMEC Journal of Traditional Chinese Medicine (English Edition). (All-China Assoc. of Traditional Chinese Medicine, Academy of Traditional Chinese Medicine) V.1- 1981- Volume(issue)/page/year: 2,31,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4228 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - tremor Behavioral - ataxia

REFERENCE :: JTCMEC Journal of Traditional Chinese Medicine (English Edition). (All-China Assoc. of Traditional Chinese Medicine, Academy of Traditional Chinese Medicine) V.1- 1981- Volume(issue)/page/year: 2,31,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1558 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CMJODS Chinese Medical Journal (Beijing, English Edition). (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1975- Adopted vol. no. 92 in 1979. Volume(issue)/page/year: 92,811,1979

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CMJODS Chinese Medical Journal (Beijing, English Edition). (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1975- Adopted vol. no. 92 in 1979. Volume(issue)/page/year: 92,811,1979

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 37,1108,1993

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >800 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: JTCMEC Journal of Traditional Chinese Medicine (English Edition). (All-China Assoc. of Traditional Chinese Medicine, Academy of Traditional Chinese Medicine) V.1- 1981- Volume(issue)/page/year: 2,31,1982 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3200 mg/kg/4D-I

TOXIC EFFECTS :: Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 21,134,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 1344 mg/kg/14D-I

TOXIC EFFECTS :: Cardiac - other changes Blood - changes in bone marrow (not otherwise specified) Blood - other changes

REFERENCE :: JTCMEC Journal of Traditional Chinese Medicine (English Edition). (All-China Assoc. of Traditional Chinese Medicine, Academy of Traditional Chinese Medicine) V.1- 1981- Volume(issue)/page/year: 2,31,1982

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
KD4170000

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

(3R)-dihydroarteannuin B acid 2-chloroethyl carbonate
Dihydroartemisinic acid
2,5,5-trimethyl-2-[2'-((1''S)-2''-formyl-6''(R)-methylcyclohex-2''-enyl)ethyl]-1,3-dioxane
2,5,5-trimethyl-2-[2'-[1''R-methyl-3''-[(trimethylsilyl)hydroxymethyl]cyclohex-3''-en-2''-yl]ethyl]-1,3-dioxane acetyl ester

DownStream

Artesunate
alpha-Dihydroartemisinin
Dihydroartemisinin
Artemotil
(3R,12aR)-3,6α,9β-Trimethyl-3β,12α-epoxy-3,4,5,5aα,6,7,8,8aα,9,10-decahydro-10α-ethoxypyrano[4,3-j]-1,2-benzodioxepin
deoxyartemisinin

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Anti-inflammatory, Antioxidant and Antimicrobial Effects of Artemisinin Extracts from Artemisia annua L.

Korean J. Physiol. Pharmacol. 19(1) , 21-7, (2015)

The anti-inflammatory, antioxidant, and antimicrobial properties of artemisinin derived from water, methanol, ethanol, or acetone extracts of Artemisia annua L. were evaluated. All 4 artemisinin-conta...

Artemisinin nanoformulation suitable for intravenous injection: Preparation, characterization and antimalarial activities.

Int. J. Pharm. 495 , 671-9, (2015)

More than 40 years after its discovery, artemisinin has become the most promising antimalarial agent. However, no intravenous formulation is available due to its poor aqueous solubility. Here, we repo...

Self-assembled biotransesterified cyclodextrins as potential Artemisinin nanocarriers. II: In vitro behavior toward the immune system and in vivo biodistribution assessment of unloaded nanoparticles.

Eur. J. Pharm. Biopharm. 88(3) , 683-94, (2014)

In a previous study, we reported on the formulation of Artemisinin-loaded surface-decorated nanoparticles (nanospheres and nanoreservoirs) by co-nanoprecipitation of PEG derivatives (PEG1500 and PEG40...

artemisinin B
Artemisinin-d3
9-epi-Artemisinin
protonated artemisinin
Dihydro ArteMisinin Dimer
dihydro-artemisinin glucuronide
Ethyl 2-amino-2-(2-ethyl-1,3-thiazol-4-yl)acetate
rac-4-[(1R,5S)-3-azabicyclo[3.1.0]hexan-1-yl]aniline
benzyl N-[1-(2-fluoroethyl)-3-hydroxycyclobutyl]carbamate
tert-butyl N-(2-fluoro-5-propanoylphenyl)carbamate
ethyl 3-(azetidin-3-yloxy)-1H-pyrazole-4-carboxylate
6-[(Prop-2-en-1-yloxy)carbonyl]-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxylic acid
5-(3-{[(Prop-2-en-1-yloxy)carbonyl]amino}prop-1-en-1-yl)pyridine-3-carboxylic acid
benzyl N-[2-(3-hydroxy-1,2-oxazol-5-yl)ethyl]carbamate
Methyl 3-(2,2-dimethyl-1,3-oxazolidin-4-yl)butanoate
tert-butyl (2S)-2-amino-4-[(methoxycarbonyl)amino]butanoate

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