Dehydromonocrotaline
Dehydromonocrotaline is a mitochondrial respiratory chain complex I NADH oxidase inhibitor, with a IC50 of 62.06 μM and a Ki of 8.1 μM in rats. Dehydromonocrotaline exerts non-competitive inhibitory effects by modifying cysteine thiol groups on complex I, and does not bind to the NADH-binding site. Dehydromonocrotaline dissipates mitochondrial membrane potential and reduces ATP levels. Dehydromonocrotaline can be used in studies related to hepatotoxicity, pulmonary hypertension and liver tumors.
For research use only. We do not sell to patients.
- CAS No.: 23291-96-5
- Formula: C16H21NO6
- Molecular Weight:323.34
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Storage:
-80°C, protect from light, stored under nitrogen
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
All Endogenous Metabolite Isoforms
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Biological Activity
Dehydromonocrotaline (100-250 μM) significantly dissipates the membrane potential of glutamate/malate-energized isolated rat liver mitochondria[1].
Dehydromonocrotaline (100-250 μM) significantly depletes ATP levels in glutamate/malate-energized isolated rat liver mitochondria[1].
Dehydromonocrotaline (62.06 μM) inhibits complex I NADH oxidase activity in rat liver submitochondrial particles with an IC50 of 62.06 μM via non-competitive inhibition (Ki = 8.1 μM)[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Dehydromonocrotaline (formed in vivo from 10 mg/kg monocrotaline; oral gavage; single dose) contributes to the generation of a set of DHP-derived DNA adducts in rat liver with a time course of formation and removal that parallels that of riddelliine, but at significantly lower maximum levels[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:F344 (female, weanling; liver tumorigenicity model via monocrotaline administration)[3]
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Dosage:Formed in vivo as metabolite of monocrotaline (10 mg/kg single oral dose)
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Administration:Oral gavage; single dose
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Result:Did not detect DHP-derived DNA adducts in liver DNA at 8 hours after monocrotaline dosing.
Reached maximum adduct levels at 7 days after treatment, then declined over time.
Dropped to levels comparable to those seen 2-3 days after dosing by 30 days after dosing.
Showed maximum adduct level 8-fold lower than that in rats treated with riddelliine.
Chemical Information
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CAS No. 23291-96-5
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Appearance Solid
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Molecular Weight 323.34
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Formula C16H21NO6
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Color White to off-white
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SMILES
O=C1O[C@@]2([H])C3=C(COC([C@](O)([C@](O)([C@H]1C)C)C)=O)C=CN3CC2
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Synonyms
Monocrotaline pyrrole; MCTP; 3,8-Didehydromonocrotaline
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Structure Classification
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Initial Source
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Shipping
Shipping with dry ice.
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Storage
-80°C, protect from light, stored under nitrogen
Solvent & Solubility
DMSO : 100 mg/mL (309.27 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (7.73 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (7.73 mM); Suspended solution
This protocol yields a suspended solution of ≥ 2.5 mg/mL (saturation unknown). Suspended solution can be used for oral and intraperitoneal injection.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation
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Data Sheet (283 KB)
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SDS (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Handling Instructions (2659 KB)
References
[1]. Mingatto FE, et al. Dehydromonocrotaline inhibits mitochondrial complex I. A potential mechanism accounting for hepatotoxicity of monocrotaline. Toxicon. 2007;50(5):724-730. [Content Brief]
[2]. Okada M, et al. A dehydromonocrotaline-induced pulmonary hypertension model in the beagle. J Thorac Cardiovasc Surg. 1995 Aug;110(2):546-7. [Content Brief]
[3]. Wang YP, et al. Metabolic activation of the tumorigenic pyrrolizidine alkaloid, retrorsine, leading to DNA adduct formation in vivo. Int J Environ Res Public Health. 2005;2(1):74-79. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
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| DMSO | 1 mM | 3.0927 mL | 15.4636 mL | 30.9272 mL | 77.3180 mL |
| 5 mM | 0.6185 mL | 3.0927 mL | 6.1854 mL | 15.4636 mL | |
| 10 mM | 0.3093 mL | 1.5464 mL | 3.0927 mL | 7.7318 mL | |
| 15 mM | 0.2062 mL | 1.0309 mL | 2.0618 mL | 5.1545 mL | |
| 20 mM | 0.1546 mL | 0.7732 mL | 1.5464 mL | 3.8659 mL | |
| 25 mM | 0.1237 mL | 0.6185 mL | 1.2371 mL | 3.0927 mL | |
| 30 mM | 0.1031 mL | 0.5155 mL | 1.0309 mL | 2.5773 mL | |
| 40 mM | 0.0773 mL | 0.3866 mL | 0.7732 mL | 1.9329 mL | |
| 50 mM | 0.0619 mL | 0.3093 mL | 0.6185 mL | 1.5464 mL | |
| 60 mM | 0.0515 mL | 0.2577 mL | 0.5155 mL | 1.2886 mL | |
| 80 mM | 0.0387 mL | 0.1933 mL | 0.3866 mL | 0.9665 mL | |
| 100 mM | 0.0309 mL | 0.1546 mL | 0.3093 mL | 0.7732 mL |
Dehydromonocrotaline Related Classifications
HY-N9279 Related Classifications
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- Dehydromonocrotaline
- 23291-96-5
- Monocrotaline pyrrole
- MCTP
- 3,8-Didehydromonocrotaline
- Endogenous Metabolite
- cysteine thiol group
- hepatotoxicity
- rat
- pulmonary hypertension
- beagles
- rat liver mitochondria
- mitochondrial respiratory chain complex I NADH oxidase
- glutathione
- pulmonary edema
- DHP-derived DNA adducts
- Inhibitor
- inhibitor
- inhibit