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| Targets |
Apovincaminic acid is an active metabolite that targets multiple pathways. Its primary mechanism is the selective inhibition of Ca2+/calmodulin-dependent cyclic nucleotide phosphodiesterase (PDE) type 1, leading to an increase in intracellular cyclic GMP (cGMP) in cerebral blood vessels, which causes vasodilation. It also exhibits neuroprotective and anti-inflammatory actions, including reducing microglia activation, making it relevant in the study of stroke and neurodegenerative diseases.
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| ln Vitro |
In vitro, apovincaminic acid exerts a neuroprotective type of action. It has been shown to reduce microglia activation, which is a key component of neuroinflammation. By doing so, it can prevent learning and memory impairment in cellular models of brain injury. Its activity is often measured by its ability to enhance cerebral blood flow or protect neurons from oxidative stress in cell culture.
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| ln Vivo |
Apovincaminic acid (10 mg/kg; intraperitoneally twice daily for 4 days) considerably reduces lesion size and the area where microglia are activated in addition to successfully attenuating behavioral abnormalities[1]. Rats administered with apovincaminic acid (10 mg/kg; po) absorb 50% of the dosage as compared to intravenous administration[2].
In vivo, apovincaminic acid is the primary active metabolite responsible for the pharmacological effects of vinpocetine. It is orally active and has been shown to effectively cross the blood-brain barrier. In animal models, it has been demonstrated to prevent learning and memory impairment (e.g., in the Morris water maze test), effectively attenuate attention deficits, and significantly reduce lesion size after brain injury. It is used in research to study cerebral ischemia, cognitive decline, and memory disorders. |
| Enzyme Assay |
For in vitro neuroprotection assays, apovincaminic acid hydrochloride is dissolved in DMSO or saline to prepare a stock solution. To test its neuroprotective effects, primary cortical neurons or neuronal cell lines (e.g., PC12 or SH-SY5Y) are cultured. The cells are subjected to an insult (e.g., oxygen-glucose deprivation (OGD) to simulate stroke or treatment with a neurotoxin). Apovincaminic acid is added to the culture at varying concentrations (e.g., 0.1-50 uM). Cell viability is measured 24-48 hours later using MTT or LDH release assays.
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| Cell Assay |
For in vitro cellular experiments, apovincaminic acid can be used as a direct treatment. For example, microglial cells (e.g., BV-2 cell line) are seeded in 6-well plates. They are pre-treated with apovincaminic acid for 1-2 hours, then stimulated with an inflammatory agent like lipopolysaccharide (LPS) to mimic an inflammatory state. After 24 hours, the cell culture supernatant is collected to measure inflammatory cytokines (e.g., IL-6, TNF-alpha) by ELISA, and the cells are lysed for Western blotting to measure markers of inflammation and cell death.
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| Animal Protocol |
Animal/Disease Models: Male Harlan‐Wistar rats (300-400 g) are injected NMDA[1]
Doses: 10 mg/kg Route of Administration: Ip twice (two times) daily for 4 days Experimental Results: Attenuated the attention deficit effectively. Prevented the learning and impairment memory in the spontaneous alternation and Morris water maze tests. Dramatically decreased lesion size microglia activation. For in vivo animal experiments, apovincaminic acid is typically administered to rodents via intraperitoneal (i.p.) injection or oral gavage to study its effects on cognition and brain injury. A common protocol is to use a rat or mouse model of cerebral ischemia (e.g., middle cerebral artery occlusion, MCAO). The compound is administered at a dose of 10 mg/kg, i.p., twice daily for 4 days, starting immediately after reperfusion. The animals are then subjected to behavioral tests (e.g., Morris water maze for spatial memory) before being sacrificed. The brains are harvested to measure lesion size using TTC staining and to analyze markers of microglia activation by immunohistochemistry. |
| ADME/Pharmacokinetics |
As an active metabolite of vinpocetine, apovincaminic acid has a favorable pharmacokinetic profile for CNS research. It is orally bioavailable and can cross the blood-brain barrier. In animal studies, it has a relatively short half-life in plasma (hours), but its effects on cerebrovascular function and neuroinflammation can be sustained. Specific parameters like Tmax, Cmax, and AUC are generally derived from studies of its parent compound, vinpocetine.
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| Toxicity/Toxicokinetics |
Apovincaminic acid hydrochloride is considered to have low toxicity and is generally well-tolerated at research doses. Vinpocetine and its metabolites have a long history of use as a dietary supplement, with few serious side effects. As a research chemical, standard safety precautions for handling organic compounds should be followed. The compound is for research use only and not intended for human consumption.
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| References |
[1]. Nyakas C, et, al. Neuroprotective effects of vinpocetine and its major metabolite cis-apovincaminic acid on NMDA-induced neurotoxicity in a rat entorhinal cortex lesion model. CNS Neurosci Ther. Summer 2009;15(2):89-99.
[2]. Pudleiner P, et, al. Study on the absorption of vinpocetine and apovincaminic acid. Eur J Drug Metab Pharmacokinet. Oct-Dec 1993;18(4):317-21. [3]. Wang M, et, al. Simultaneous Determination of Vinpocetine and its Major Active Metabolite Apovincaminic Acid in Rats by UPLC-MS/MS and its Application to the Brain Tissue Distribution Study. J Chromatogr Sci. 2018 Mar 1;56(3):225-232. |
| Additional Infomation |
Apovincaminic acid hydrochloride is not a drug but a research-grade active metabolite. It is used as an analytical standard for pharmacokinetic studies of vinpocetine. It is also a valuable biochemical tool for studying the mechanisms of neuroprotection, neuroinflammation, and cognitive enhancement. Its effects on cerebral blood flow and microglial activation make it relevant to research on Alzheimer's disease, stroke, and traumatic brain injury.
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| Molecular Formula |
C20H23CLN2O2
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| Molecular Weight |
358.86
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| Exact Mass |
358.144
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| CAS # |
72296-47-0
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| PubChem CID |
131667715
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| Appearance |
Off-white to yellow solid powder
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
25
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| Complexity |
588
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| Defined Atom Stereocenter Count |
2
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| SMILES |
Cl.OC(C1=C[C@]2(CC)CCCN3CCC4C5C=CC=CC=5N1C=4[C@@H]32)=O
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| InChi Key |
LXMYBTYOASVVKL-VDWUQFQWSA-N
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| InChi Code |
InChI=1S/C20H22N2O2.ClH/c1-2-20-9-5-10-21-11-8-14-13-6-3-4-7-15(13)22(17(14)18(20)21)16(12-20)19(23)24;/h3-4,6-7,12,18H,2,5,8-11H2,1H3,(H,23,24);1H/t18-,20+;/m1./s1
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| Chemical Name |
(15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylic acid;hydrochloride
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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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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: 50 mg/mL (139.33 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7866 mL | 13.9330 mL | 27.8660 mL | |
| 5 mM | 0.5573 mL | 2.7866 mL | 5.5732 mL | |
| 10 mM | 0.2787 mL | 1.3933 mL | 2.7866 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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