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Isorhynchophylline

Cat No.:V29632 Purity: ≥98%
Isorhynchophylline (IRN) is an alkaloid isolated from Uncaria rhynchophylla, it has the effects of lowered blood pressure, vasodilatation and protection against ischemia-induced neuronal damage.
Isorhynchophylline
Isorhynchophylline Chemical Structure CAS No.: 6859-01-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Isorhynchophylline (IRN) is an alkaloid isolated from Uncaria rhynchophylla, it has the effects of lowered blood pressure, vasodilatation and protection against ischemia-induced neuronal damage.
Isorhynchophylline (CAS 6859-01-4) is an oxindole alkaloid that is the main active ingredient of Uncaria rhynchophylla, a plant used in traditional Chinese medicine. With a molecular formula of C₂₂H₂₈N₂O₄ and a molecular weight of 384.46 g/mol, it exhibits diverse biological activities. It has neuroprotective, anticancer, and antihypertensive properties. It lowers blood pressure, induces vasodilatation, and provides protection against ischemia-induced neuronal damage. It also exhibits antidepressant-like effects in mice, at least in part by inhibiting monoamine oxidase.
Biological Activity I Assay Protocols (From Reference)
Targets
Isorhynchophylline targets multiple pathways. It inhibits monoamine oxidase, contributing to its antidepressant-like effects. It suppresses rat blood vessel contraction and counteracts angiotensin II's hypertensive effect. Its neuroprotective effects are likely mediated through its anti-inflammatory and antioxidant activities. It enhances cognitive function and protects against neuronal damage.
ln Vitro
In vitro, Isorhynchophylline exhibits neuroprotective, anticancer, and antihypertensive activities. It suppresses blood vessel contraction. It has anti-inflammatory effects. Its ability to inhibit monoamine oxidase has been demonstrated. These activities are measured in various cell-based and tissue-based assays.
ln Vivo
In vivo, Isorhynchophylline (10-40 mg/kg) exhibits antidepressant-like effects in mice. It lowers blood pressure and provides protection against ischemia-induced neuronal damage. It enhances cognitive function and protects against neuronal damage, showing potential in Alzheimer’s and Parkinson’s disease research.
Enzyme Assay
In vitro non-cell enzyme assays for Isorhynchophylline typically involve measuring the inhibition of monoamine oxidase (MAO) activity. The compound is incubated with the enzyme and a substrate, and the production of the oxidized product is measured. Its effects on angiotensin-converting enzyme (ACE) could also be assessed in a cell-free system.
Cell Assay
In vitro cell-based assays for Isorhynchophylline use neuronal cell lines to study its neuroprotective effects against various insults, such as oxidative stress or excitotoxicity. Its effects on cancer cell lines can be studied to assess its anticancer activity. Its anti-inflammatory activity is studied in immune cells by measuring cytokine production.
Animal Protocol
In vivo animal studies for Isorhynchophylline employ models of depression (e.g., forced swim test), hypertension (e.g., spontaneously hypertensive rats), and neurodegeneration (e.g., models of Alzheimer's or Parkinson's disease). The compound is administered, and behavioral, physiological, and biochemical parameters are assessed.
ADME/Pharmacokinetics
Isorhynchophylline has a molecular weight of 384.46 g/mol and a molecular formula of C₂₂H₂₈N₂O₄. It is an oxindole alkaloid. It is soluble in DMSO. As a small, lipophilic molecule, it is expected to be orally bioavailable and to cross the blood-brain barrier. Detailed pharmacokinetic data are available from preclinical studies.
Toxicity/Toxicokinetics
The toxicity profile of Isorhynchophylline is not extensively detailed in the provided search results. As a natural product from Uncaria rhynchophylla, which has a history of use, it is generally considered to have a good safety profile. However, comprehensive toxicological studies are required for therapeutic development.
References

[1]. Isorhynchophylline improves learning and memory impairments induced by D-galactose in mice. Neurochemistry International Volume 76, October 2014, Pages 42–49.

[2]. Isorhynchophylline protects against pulmonary arterial hypertension and suppresses PASMCs proliferation. Biochem Biophys Res Commun. 2014 Jul 18;450(1):729-34.

[3]. Inhibitory effect of isorhynchophylline on cardiomyocyte hypertrophy induced by angiotensinⅡ. West China JOurnal of Pharmaceutical Sciences, 2013-05.

Additional Infomation
Isorhynchophylline is an indoleazine compound and a metabolite. It has been reported to exist in Uncaria sinensis, Uncaria macrophylla, and other organisms with relevant data. See also: Nepeta cataria (partial).
Isorhynchophylline is an oxindole alkaloid from Uncaria rhynchophylla with neuroprotective, anticancer, and antihypertensive properties. It exhibits antidepressant-like effects and enhances cognitive function. It is also known as (+)-Isorhynchophylline. It is not approved for clinical use and is intended for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H28N2O4
Molecular Weight
384.4687
Exact Mass
384.204
CAS #
6859-01-4
PubChem CID
3037048
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
447.6±25.0 °C at 760 mmHg
Melting Point
114ºC
Flash Point
224.5±23.2 °C
Vapour Pressure
0.0±1.1 mmHg at 25°C
Index of Refraction
1.677
LogP
1.9
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
5
Heavy Atom Count
28
Complexity
663
Defined Atom Stereocenter Count
4
SMILES
CC[C@H]1CN2CC[C@@]3([C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)C4=CC=CC=C4NC3=O
InChi Key
DAXYUDFNWXHGBE-VKCGGMIFSA-N
InChi Code
InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22-/m0/s1
Chemical Name
methyl (E)-2-[(3S,6'R,7'S,8'aS)-6'-ethyl-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate
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

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 : ~100 mg/mL (~260.10 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.75 mg/mL (7.15 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 27.5 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: ≥ 2.75 mg/mL (7.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 27.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.6010 mL 13.0049 mL 26.0098 mL
5 mM 0.5202 mL 2.6010 mL 5.2020 mL
10 mM 0.2601 mL 1.3005 mL 2.6010 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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)
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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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