| Size | Price | Stock | Qty |
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| 1mg |
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| 2mg | |||
| 10mg | |||
| Other Sizes |
| Targets |
Reticuline acts as an inhibitor of the JAK2/STAT3 and NF-κB signaling pathways. It reduces the phosphorylation levels of JAK2 and STAT3 and inhibits the mRNA expression of pro-inflammatory cytokines such as TNF-α and IL-6.
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| ln Vitro |
In isolated rat aortic rings with intact endothelium, treticuline (3 μM, 30 μM, 300 μM, 900 μM, and 1.5 mM) suppresses contractions generated by phenylephrine (1 μM), KCl (80 mM), and KCl (30 mM) in a concentration-dependent manner (IC50= 40) ±10, 240±40, and 300±40 μM, respectively. Reticuline at concentrations of 3 μM, 30 μM, 300 μM, 900 μM, and 1.5 mM prevented intracellular calcium-dependent transient contraction generated by norepinephrine (1 μM), but caffeine at concentrations of 20 mM did not cause intracellular calcium-dependent transient contraction. 2].
In vitro, reticuline concentration-dependently inhibits contractions induced by phenylephrine and KCl in aortic rings, with IC50 values ranging from 40 to 300 μM. It suppresses CaCl2-induced contraction and calcium transients triggered by the release of intracellular calcium stores. |
| ln Vivo |
Injections of reticuline (5, 10, and 20 mg/kg, i.v., random) elicited severe hypotension in normotensive rats. The hypotensive effects of reticuline may be related to peripheral vasodilation: 1) muscarinic stimulation and NOS activation in vascular endothelial cells, 2) voltage-dependent Ca2+ channel blockage and/or 3) inhibition of demethylation Adrenaline-sensitive intracellular release of Ca2+ storage [2].
In vivo, reticuline (5, 10, and 20 mg/kg, intravenous) induces significant hypotensive responses in normotensive Wistar rats, accompanied by an increased heart rate. It also alleviates oedema in rats. Furthermore, it produces CNS effects like prolongation of pentobarbital-induced sleep and suppression of conditioned avoidance response. |
| Enzyme Assay |
The in vitro vasorelaxant effect of reticuline is studied using aortic rings. The compound's ability to inhibit contractions induced by phenylephrine or KCl is measured in the presence or absence of endothelium and various inhibitors like L-NAME or atropine to elucidate its mechanism.
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| Cell Assay |
Cell-based assays are not the primary focus for this natural product. Its in vitro activity is predominantly characterized in tissue-based functional assays, such as the aortic ring model described, which measures the compound's effect on vascular smooth muscle contraction.
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| Animal Protocol |
The hypotensive effect of reticuline is evaluated in normotensive Wistar rats following intravenous administration. Blood pressure and heart rate are monitored to assess its cardiovascular effects. Pretreatment with L-NAME or atropine is used to investigate the mechanism of the hypotensive response.
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| ADME/Pharmacokinetics |
Specific pharmacokinetic data for reticuline is not detailed in the available literature. As a natural alkaloid, its absorption, distribution, metabolism, and excretion would be typical of small molecules, but these properties would need to be characterized in dedicated pharmacokinetic studies.
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| Toxicity/Toxicokinetics |
Specific toxicity data is not available. However, as a natural product with CNS and cardiovascular effects, its safety profile would be an important area for further research. The compound's effects on blood pressure and heart rate indicate a need for careful cardiovascular safety assessment.
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| References | |
| Additional Infomation |
(S)-Reticulin is the (S)-enantiomer of reticulin. It is an EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-theobromine 4'-O-methyltransferase] inhibitor. It is the conjugate base of (S)-reticulin (1+). It is the enantiomer of (R)-reticulin. Reticulin has been reported in Neolitsea aciculata, Magnolia officinalis, and other organisms with relevant data. See also: Peumus boldus leaf (partial).
Reticuline is a promising natural product for studying inflammation and hypertension. Its dual inhibition of the JAK2/STAT3 and NF-κB pathways makes it a valuable tool for investigating inflammatory diseases. Its cardiovascular effects also position it as a lead for antihypertensive drug development. |
| Molecular Formula |
C19H23NO4
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|---|---|
| Molecular Weight |
329.39
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| Exact Mass |
329.162
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| CAS # |
485-19-8
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| Related CAS # |
(R)-Reticuline;3968-19-2;1699-46-3;Reticuline;
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| PubChem CID |
439653
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| Appearance |
White to yellow solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
504.9±50.0 °C at 760 mmHg
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| Melting Point |
125-126ºC
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| Flash Point |
259.2±30.1 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.604
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| LogP |
2.09
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
24
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| Complexity |
407
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC
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| InChi Key |
BHLYRWXGMIUIHG-HNNXBMFYSA-N
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| InChi Code |
InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1
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| Chemical Name |
(S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
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| Synonyms |
d-ReticulineReticuline S-(+)-Reticuline EINECS 207-611-3；1699-46-3；
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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 (~303.59 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.59 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 (7.59 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0359 mL | 15.1796 mL | 30.3591 mL | |
| 5 mM | 0.6072 mL | 3.0359 mL | 6.0718 mL | |
| 10 mM | 0.3036 mL | 1.5180 mL | 3.0359 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT04470050 | Completed | Drug: Dexmedetomidine Drug: Placebo |
Opioid Withdrawal | BioXcel Therapeutics Inc | 2020-06-09 | Phase 1 Phase 2 |
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