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| ln Vitro |
The sole thing that separates deserpidine from reserpine, a strong ganglionic blocker, is the lack of a methoxy group at C-11. Treatments for psychosis and hypertension include deserpine. Deserpine may also be helpful as a controlling medication for additional cardiac conditions [1][2].
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| ln Vivo |
A sensitive and rapid liquid chromatography/tandem mass spectrometric (LC/MS/MS) method was developed and validated for the determination of deserpidine in human plasma. The plasma samples were prepared using liquid-liquid extraction (LLE) with ethyl ether-dichloromethane (3:2, v/v). Chromatographic separation was accomplished on an Ultimate XB-C18 column. The mobile phase consisted of methanol-5mM ammonium acetate-formic acid (72:28:0.036, v/v/v). Detection of deserpidine and the internal standard tropisetron was achieved by tandem mass spectrometry with an electrospray ionization interface in positive ion mode. The lower limit of quantification was 4.0pg/ml. The linear range of the method was from 4.0 to 2000pg/ml. The intra- and inter-day precisions were lower than 14.7% in terms of relative standard deviation (RSD), and the accuracy was within +/-8.7% in terms of relative error (RE). This validated method was successfully applied for the evaluation of pharmacokinetics of deserpidine after a single oral administration dose of 0.25mg deserpidine to 22 healthy volunteers [2].
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| Enzyme Assay |
The Rauwolfia alkaloids reserpine (1) and deserpidine (2), two alkaloids from Rauwolfia species, have been widely used for their antihypertensive action. Deserpidine (2) is a compound with limited availability from natural sources, and its synthesis from 1 in six steps (41% overall yield) is reported here [1].
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| Toxicity/Toxicokinetics |
Rat intravenous LD50 15 mg/kg, Psychotropic Drugs and Related Compounds, 2nd ed., E. Usdin and DH Efron, Washington, D.C., 1972, -(104), 1972. Mouse oral LD50 500 mg/kg, behavior: coma; lung, pleural or respiratory: dyspnea; gastrointestinal: hypermotility, diarrhea, Journal of the American Pharmacist Association, Science Edition, 44(688), 1955. Mouse intraperitoneal LD50 60 mg/kg, behavior: coma; lung, pleural or respiratory: dyspnea; gastrointestinal: hypermotility, diarrhea, Journal of the American Pharmacist Association (Science Edition), 44(688), 1955.
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| References | |
| Additional Infomation |
Deserpidine is an alkaloid ester, methyl ester, benzoate ester, organic heteropentane compound, and yohimbine alkaloid. It is derived from the hydride of yohimbine. Deserpidine is an ester alkaloid drug isolated from Rauvolfia oleracea (Apocynaceae family), possessing antipsychotic and antihypertensive effects, and has been used to control hypertension and alleviate psychotic behaviors. Deserpidine is a catecholamine-depleting sympathomimetic agent. Its physiological action is achieved by reducing sympathetic nerve activity. Deserpidine has been reported in Aspergillus flavus, Ophiopogon japonicus, and other organisms with relevant data. Deserpidine is an ester alkaloid derived from Rauvolfia oleracea with antihypertensive activity. Deserpidine is a competitive inhibitor of angiotensin-converting enzyme (ACE). Deserpidine blocks the conversion of angiotensin I to angiotensin II by competing with angiotensin I for ACE, and angiotensin II is a potent vasoconstrictor. Decreased serum angiotensin II levels lead to a decrease in blood pressure. Deserpidine can also reduce adrenal cortex-stimulated aldosterone secretion in response to angiotensin II. See also: Deserpidine; Methoxythiazide (component); Deserpidine; Hydrochlorothiazide (component). Drug Indications For the treatment of hypertension. Mechanism of Action Deserpidine's mechanism of action is through inhibition of the ATP/Mg²⁺ pump, which is responsible for isolating neurotransmitters into storage vesicles located in presynaptic neurons. Neurotransmitters not stored in vesicles are readily metabolized by monoamine oxidase (MAO), leading to a decrease in catecholamine levels. Pharmacodynamics Deserpidine is an alkaloid from Rauwolfia canescens and is used as an antihypertensive drug. Rauwolfia alkaloids act by controlling nerve impulses in specific neural pathways. Therefore, they act on the heart and blood vessels, thereby lowering blood pressure.
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| Molecular Formula |
C32H38N2O8
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| Molecular Weight |
578.65
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| Exact Mass |
578.262
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| Elemental Analysis |
C, 66.42; H, 6.62; N, 4.84; O, 22.12
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| CAS # |
131-01-1
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| Related CAS # |
6033-69-8 (HCl);131-01-1;
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| PubChem CID |
8550
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
676.1±55.0 °C at 760 mmHg
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| Melting Point |
~275 °C (dec.)(lit.)
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| Flash Point |
362.7±31.5 °C
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| Vapour Pressure |
0.0±2.1 mmHg at 25°C
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| Index of Refraction |
1.626
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| Source |
Rauwolfia canescens
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| LogP |
4.19
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
42
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| Complexity |
953
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| Defined Atom Stereocenter Count |
6
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| SMILES |
CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=CC=CC=C45)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
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| InChi Key |
CVBMAZKKCSYWQR-WCGOZPBSSA-N
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| InChi Code |
InChI=1S/C32H38N2O8/c1-37-24-12-17(13-25(38-2)29(24)39-3)31(35)42-26-14-18-16-34-11-10-20-19-8-6-7-9-22(19)33-28(20)23(34)15-21(18)27(30(26)40-4)32(36)41-5/h6-9,12-13,18,21,23,26-27,30,33H,10-11,14-16H2,1-5H3/t18-,21+,23-,26-,27+,30+/m1/s1
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| Chemical Name |
methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
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| Synonyms |
DESERPIDINE; DESERPIDINE; 131-01-1; Harmonyl; Raunormine; Recanescin; Deserpidin; Recanescine; Canescine;Raunormine; Harmonyl
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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 (~172.82 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.32 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 (4.32 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 25.0 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 | 1.7282 mL | 8.6408 mL | 17.2816 mL | |
| 5 mM | 0.3456 mL | 1.7282 mL | 3.4563 mL | |
| 10 mM | 0.1728 mL | 0.8641 mL | 1.7282 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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