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Details

Stereochemistry ACHIRAL
Molecular Formula C12H16O3
Molecular Weight 208.2536
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-ASARONE

SMILES

COC1=CC(OC)=C(OC)C=C1\C=C\C

InChI

InChIKey=RKFAZBXYICVSKP-AATRIKPKSA-N
InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+

HIDE SMILES / InChI

Molecular Formula C12H16O3
Molecular Weight 208.2536
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/29042206 | https://www.ncbi.nlm.nih.gov/pubmed/29032344 | https://www.ncbi.nlm.nih.gov/pubmed/15679319 | https://www.ncbi.nlm.nih.gov/pubmed/25311563 |

α-Asarone is a phytochemical compound with neuroprotective, anti-oxidative, anticonvulsive and cognitive enhancing action, isolated from the Chinese medicinal herb Acorus tatarinowii. Numerous clinical studies in China had indicated the effectiveness of α-asarone against respiratory disorders and epilepsy. Asarone tablets have been clinically used as bronchial asthma and bronchitis prescription drug in China. Unfortunately, toxic and genotoxic studies of a-asarone have indicated that this compound may pose a risk to human health, including embryotoxicity and maternal toxicity in rats, hepatotoxicity in rat-cultivated hepatocytes, and in vivo and in vitro genotoxic damage in mammalian cells.

CNS Activity

Curator's Comment: Known to be CNS penetrant in mouse. Human data not available

Originator

Sources: Berichte der Deutschen Chemischen Gesellschaft 22, 3172-6

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
92.3 µM [IC50]
5.86 µM [IC50]
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Alpha-asarone attenuates depression-like behavior in nicotine-withdrawn mice: Evidence for the modulation of hippocampal pCREB levels during nicotine-withdrawal.
2018 Jan 5
Patents

Patents

Sample Use Guides

ICR mice/ Male: 10,15,20, 30, 50 and 100mg/kg i.p. Swiss albino mice/male: 1. 7, 3.5, 7, and 14; p.o.; o.d.× 7 days SD rats/ male: 50, 100 and 200; i.p.; o.d.× 21 days Wistar rats/male: 20 mg/kg, i.v.
Route of Administration: Other
BV-2 microglial cells were used for activity evaluation. Cells were cultured in DMEM supplemented with 5% FBS and 50 mkg/mL penicillin-streptomycin in a 37 C humidified incubator supplied with 5% CO2 and 95% O2. The cells were seeded at a density of 5 x 10^4 cells/mL and were pretreated for 1 h with various concentrations of a-asarone (10, 50 and 250 mkM) followed by an incubation with LPS (100 ng/mL) for the indicated times (30 min and 6, 18 and 24 h).
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:18:12 GMT 2023
Edited
by admin
on Fri Dec 15 17:18:12 GMT 2023
Record UNII
DQY9PNE5FK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.ALPHA.-ASARONE
Systematic Name English
BENZENE, 1,2,4-TRIMETHOXY-5-PROPENYL-, (E)-
Common Name English
ASARONE [HSDB]
Common Name English
.ALPHA.-ASARON
Common Name English
ETHEROPHENOL
Common Name English
ASARONE, ALPHA-
Systematic Name English
ASARUM CAMPHOR
Common Name English
ASARABACCA CAMPHOR
Common Name English
(E)-ASARONE
Common Name English
ASARON
Common Name English
ASARONE
HSDB  
Common Name English
TRANS-ISOASARON
Common Name English
BENZENE, 1,2,4-TRIMETHOXY-5-(1E)-1-PROPENYL-
Systematic Name English
BENZENE, 1,2,4-TRIMETHOXY-5-(1E)-1-PROPEN-1-YL-
Systematic Name English
1,2,4-TRIMETHOXY-5-PROPENYLBENZENE
Systematic Name English
ISOASARON
Common Name English
BENZENE, 1,2,4-TRIMETHOXY-5-(1-PROPENYL)-, (E)-
Common Name English
Asarone [WHO-DD]
Common Name English
TRANS-ASARONE
Common Name English
TRANS-ISOASARONE
Common Name English
Code System Code Type Description
SMS_ID
100000151877
Created by admin on Fri Dec 15 17:18:12 GMT 2023 , Edited by admin on Fri Dec 15 17:18:12 GMT 2023
PRIMARY
ECHA (EC/EINECS)
220-743-6
Created by admin on Fri Dec 15 17:18:12 GMT 2023 , Edited by admin on Fri Dec 15 17:18:12 GMT 2023
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EVMPD
SUB126297
Created by admin on Fri Dec 15 17:18:12 GMT 2023 , Edited by admin on Fri Dec 15 17:18:12 GMT 2023
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EPA CompTox
DTXSID00871878
Created by admin on Fri Dec 15 17:18:12 GMT 2023 , Edited by admin on Fri Dec 15 17:18:12 GMT 2023
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PUBCHEM
636822
Created by admin on Fri Dec 15 17:18:12 GMT 2023 , Edited by admin on Fri Dec 15 17:18:12 GMT 2023
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MESH
C012195
Created by admin on Fri Dec 15 17:18:12 GMT 2023 , Edited by admin on Fri Dec 15 17:18:12 GMT 2023
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RXCUI
2375532
Created by admin on Fri Dec 15 17:18:12 GMT 2023 , Edited by admin on Fri Dec 15 17:18:12 GMT 2023
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CHEBI
78309
Created by admin on Fri Dec 15 17:18:12 GMT 2023 , Edited by admin on Fri Dec 15 17:18:12 GMT 2023
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HSDB
3464
Created by admin on Fri Dec 15 17:18:12 GMT 2023 , Edited by admin on Fri Dec 15 17:18:12 GMT 2023
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FDA UNII
DQY9PNE5FK
Created by admin on Fri Dec 15 17:18:12 GMT 2023 , Edited by admin on Fri Dec 15 17:18:12 GMT 2023
PRIMARY
CAS
2883-98-9
Created by admin on Fri Dec 15 17:18:12 GMT 2023 , Edited by admin on Fri Dec 15 17:18:12 GMT 2023
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WIKIPEDIA
ASARONE
Created by admin on Fri Dec 15 17:18:12 GMT 2023 , Edited by admin on Fri Dec 15 17:18:12 GMT 2023
PRIMARY