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| 5mg |
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| 10mg |
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Reticuline is a novel and potent opium alkaloid acting as a dopamine receptor blocker. It also has anti-inflammatory activity by inhibiting JAK2/STAT3 and NF-κB signaling pathways. It can inhibit the mRNA levels of TNF-α, and IL-6 and reduce the phosphorylation levels of JAK2 and STAT3.
| 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].
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| 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].
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| References | |
| Additional Infomation |
(S)-reticuline is the (S)-enantiomer of reticuline. It has a role as an EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor. It is a conjugate base of a (S)-reticulinium(1+). It is an enantiomer of a (R)-reticuline.
Reticuline has been reported in Neolitsea aciculata, Magnolia officinalis, and other organisms with data available. See also: Peumus boldus leaf (part of). |
| 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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