| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg | |||
| Other Sizes |
| Targets |
Thujone acts as a reversible modulator of the GABAA receptor, with an IC50 of 21 μM for inhibiting GABA-induced currents. It also acts as an inhibitor of acetylcholinesterase (ACh) with an IC50 of 24.7 μM. It induces ROS accumulation-dependent cytotoxicity and causes cell apoptosis and autophagy. It has been thought to act as an inhibitor of acyl-CoA activity in brain synaptosomes.
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| ln Vitro |
Thujone induces ROS-dependent cell toxicity and causes apoptosis and autophagy. It has antinociceptive, insecticidal, and anthelmintic activity. It inhibits ACh with an IC50 of 24.7 μM. In vivo, thujone at 1.25 mg/kg (i.p.) significantly impaired nicotine-induced enhancement of learning and memory in Wistar rats.
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| ln Vivo |
In vivo, thujone (1.25 mg/kg, i.p.) significantly impaired nicotine-induced enhancement of learning and memory in Wistar rats in the one-trial passive avoidance paradigm. Oral doses of 10-100 mg/kg in mice showed no effect on respiratory activity of the cerebral cortex. It readily penetrates the blood-brain barrier. Its known metabolites include 4-hydroxy-α-thujone and 7-hydroxy-α-thujone.
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| Enzyme Assay |
In vitro enzyme assays for Thujone can measure its inhibition of GABAA receptor function using electrophysiological techniques or radioligand binding assays. Its inhibition of ACh can be measured using colorimetric or fluorometric assays. Its effects on ROS production can be assessed using fluorescent probes in cell-free systems.
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| Cell Assay |
In vitro cellular assays for Thujone involve treating cells with the compound and measuring cytotoxicity, apoptosis, and autophagy. ROS accumulation can be detected using fluorescent dyes such as DCFH-DA. Its effects on cell viability are measured using MTT or similar assays. Its neurotoxicity or neuroprotection can be studied in neuronal cell cultures.
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| Animal Protocol |
In vivo animal models for Thujone are used to study its effects on the central nervous system. The one-trial passive avoidance paradigm in rats is used to assess its effects on learning and memory. Its antinociceptive effects can be studied in models of pain, such as the hot plate or tail-flick tests. Its insecticidal and anthelmintic activities are evaluated in appropriate parasite models.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Alpha-thujone's known metabolites include 4-hydroxy-α-thujone and 7-hydroxy-α-thujone. Thujone is readily absorbed after oral administration and penetrates the blood-brain barrier. Its known metabolites include 4-hydroxy-α-thujone and 7-hydroxy-α-thujone. Its pharmacokinetics are influenced by its lipophilic nature. It is metabolized in the liver by cytochrome P450 enzymes, and its metabolites are excreted in urine. |
| Toxicity/Toxicokinetics |
Thujone is a neurotoxic compound that can cause seizures and other neurological effects at high doses. Its toxicity is primarily due to its modulation of GABAA receptors. It has been associated with the neurotoxic effects of absinthe consumption. It is classified as a potential toxin and should be handled with care. Its safety in humans has not been established for therapeutic use.
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| References |
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| Additional Infomation |
(-)-α-thujone is the (1S,4R,5R)- stereoisomer of α-thujone, and is the enantiomer of (+)-α-thujone. α-thujone has been reported to exist in rosemary (Salvia rosmarinus), wormwood (Artemisia Thuscula), and other organisms with relevant data. See also: wormwood (Artemisia absinthium), whole plant (partial).
Thujone is a bicyclic monoterpene ketone and the principal neuroactive component of wormwood oil and absinthe. It is a reversible modulator of the GABAA receptor (IC50 = 21 μM) and an ACh inhibitor. It induces ROS-dependent cytotoxicity, apoptosis, and autophagy. It has antinociceptive, insecticidal, and anthelmintic activities and penetrates the BBB. |
| Molecular Formula |
C10H16O
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|---|---|
| Molecular Weight |
152.24
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| Exact Mass |
152.12
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| CAS # |
546-80-5
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| PubChem CID |
261491
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.914 g/mL at 20ºC(lit.)
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| Boiling Point |
84-86ºC17 mm Hg(lit.)
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| Melting Point |
181ºC
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| Flash Point |
148 °F
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| Index of Refraction |
n20/D 1.450
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| LogP |
2.257
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
207
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| Defined Atom Stereocenter Count |
3
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| SMILES |
CC1C2CC2(CC1=O)C(C)C
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| InChi Key |
USMNOWBWPHYOEA-MRTMQBJTSA-N
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| InChi Code |
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1
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| Chemical Name |
(1S,4R,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
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| Synonyms |
Absinthol; Thujone
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~656.90 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.42 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (16.42 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (16.42 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.5686 mL | 32.8429 mL | 65.6858 mL | |
| 5 mM | 1.3137 mL | 6.5686 mL | 13.1372 mL | |
| 10 mM | 0.6569 mL | 3.2843 mL | 6.5686 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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