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Yohimbic acid

Alias: NSC 95096; NSC-95096; Yohimbic acid
Cat No.:V28419 Purity: ≥98%
Yohimbic acid is an amphoteric demethylated analogue of Yohimbine.
Yohimbic acid
Yohimbic acid Chemical Structure CAS No.: 522-87-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
25mg
100mg
250mg
Other Sizes

Other Forms of Yohimbic acid:

  • Yohimbic acid monohydrate
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Yohimbic acid is an amphoteric demethylated analogue of Yohimbine. Yohimbic acid displays vasodilatory effects and may be utilized in osteoarthritis (OA) research.
Yohimbic acid is an amphoteric demethylated analogue of Yohimbine. It is a natural alkaloid found in the bark of the African yohimbe tree (Pausinystalia johimbe). The compound has a molecular formula of C20H24N2O3 and a molecular weight of 340.42 g/mol. It displays vasodilatory effects and may be utilized in osteoarthritis (OA) research. It has been used in traditional medicine to treat various ailments, including erectile dysfunction, anxiety, and depression.
Biological Activity I Assay Protocols (From Reference)
Targets
Yohimbic acid is a weak inhibitor of topoisomerase 1/2 with µM-level activity. It displays vasodilatory effects. As a demethylated analogue of Yohimbine, it may also interact with adrenergic receptors, though further research is needed to identify and characterize its primary molecular targets.
ln Vitro
Yohimbic acid displays vasodilatory effects. It is a weak inhibitor of topoisomerase 1/2 with µM-level activity. The compound may be utilized in osteoarthritis (OA) research. Further studies are needed to fully characterize its in vitro pharmacological profile and to determine its potency against various targets.
ln Vivo
Specific in vivo activity data for Yohimbic acid are not extensively reported in the available literature. As a compound with vasodilatory effects, it may exhibit efficacy in preclinical models of cardiovascular disease. It may also be useful in osteoarthritis research. Further research is needed to characterize its pharmacokinetic and pharmacodynamic profiles in animal models.
Enzyme Assay
The in vitro assay for Yohimbic acid typically involves measuring its effects on enzyme activity or receptor binding using standard biochemical techniques. The compound may be tested for its ability to inhibit topoisomerase 1/2 or to bind to adrenergic receptors. The IC50 value is determined from the dose-response curve.
Cell Assay
The in vitro cellular assay for Yohimbic acid typically involves culturing relevant cell lines (e.g., vascular smooth muscle cells, cancer cells) in appropriate growth media. Cells are treated with varying concentrations of the compound, and cellular responses such as cell proliferation, vasodilation, or apoptosis are measured using standard assays.
Animal Protocol
In vivo animal studies for Yohimbic acid would typically involve the use of rodent models of cardiovascular disease or osteoarthritis. Animals would be administered the compound via appropriate routes (e.g., oral gavage or intraperitoneal injection) at various dose levels. Parameters such as blood pressure, vascular function, or joint health would be assessed.
ADME/Pharmacokinetics
Yohimbic acid has a molecular weight of 340.42 g/mol and a molecular formula of C20H24N2O3. The IUPAC name is (1R,2S,4aR,13bS,14aS)-2-Hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid. The compound has a purity of ≥98%. Further detailed physicochemical properties are available from the manufacturer's data sheets.
Toxicity/Toxicokinetics
Specific toxicology data for Yohimbic acid are not available in the public domain. The compound is intended for research use only and should be handled with appropriate laboratory safety precautions. Standard safety assessments would be required before any clinical application. Researchers should consult the safety data sheet for detailed handling and disposal information.
References

[1]. Significantly dysregulated genes in osteoarthritic labrum cells identified through gene expression profiling. Mol Med Rep. 2019 Aug; 20(2): 1716-1724.

[2]. HAMET R. [Sympatholytic activity and toxicity of an amphoteric demethylated derivative of yohimbine: yohimbic acid]. C R Hebd Seances Acad Sci. 1951 Oct 29;233(18):1069-71.

[3]. HAMET R. [Demonstration of the direct vasodilatory action of yohimbic acid and Py-tetrahydroquinoline]. C R Hebd Seances Acad Sci. 1960 Jun 27;250:4473-5.

Additional Infomation
Yohimbic acid is a yohimbine alkaloid that functions similarly to 17α-yohimbine.
Yohimbic acid is an amphoteric demethylated analogue of Yohimbine. It is a natural alkaloid found in the bark of the African yohimbe tree (Pausinystalia johimbe). It displays vasodilatory effects and may be utilized in osteoarthritis (OA) research. It has been used in traditional medicine to treat various ailments. The compound is also known by the synonyms NSC-95096 and YOHIMBIC ACID [INN]. It has not yet entered clinical trials and is strictly for preclinical research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H24N2O3
Molecular Weight
340.423
Exact Mass
340.179
CAS #
522-87-2
Related CAS #
Yohimbic acid hydrate;207801-27-2
PubChem CID
72131
Appearance
White to off-white solid powder
Density
1.39g/cm3
Boiling Point
600ºC at 760mmHg
Melting Point
267-268ºC (dec.)(lit.)
Flash Point
316.6ºC
Index of Refraction
1.702
LogP
2.496
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
25
Complexity
541
Defined Atom Stereocenter Count
5
SMILES
C1C[C@@H]([C@@H]([C@@H]2[C@@H]1CN3CCC4=C([C@@H]3C2)NC5=CC=CC=C45)C(=O)O)O
InChi Key
AADVZSXPNRLYLV-GKMXPDSGSA-N
InChi Code
InChI=1S/C20H24N2O3/c23-17-6-5-11-10-22-8-7-13-12-3-1-2-4-15(12)21-19(13)16(22)9-14(11)18(17)20(24)25/h1-4,11,14,16-18,21,23H,5-10H2,(H,24,25)/t11-,14-,16-,17-,18+/m0/s1
Chemical Name
(1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid
Synonyms
NSC 95096; NSC-95096; Yohimbic acid
HS Tariff Code
2934.99.9001
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 (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~125 mg/mL (~367.19 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.11 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 20.8 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: ≥ 2.08 mg/mL (6.11 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 20.8 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9375 mL 14.6877 mL 29.3755 mL
5 mM 0.5875 mL 2.9375 mL 5.8751 mL
10 mM 0.2938 mL 1.4688 mL 2.9375 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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