ChemSpider 2D Image | (−)-reserpine | C33H40N2O9

(−)-reserpine

  • Molecular FormulaC33H40N2O9
  • Average mass608.679 Da
  • Monoisotopic mass608.273376 Da
  • ChemSpider ID5566

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(−)-reserpine
(-)-reserpine
(1S,2R,3R,4aS,13bR,14aS)-2,11-diméthoxy-3-{[(3,4,5-triméthoxyphényl)carbonyl]oxy}-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodécahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoléine-1-carboxylate de méthyle [French]
(3β, 16β, 17α, 18β, 20α)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester
(3β,16β,17α,18β,20α)-11,17-Diméthoxy-18-[(3,4,5-triméthoxybenzoyl)oxy]yohimban-16-carboxylate de méthyle [French] [ACD/IUPAC Name]
102014 [Beilstein]
200-047-9 [EINECS]
4-25-00-01319 [Beilstein]
50-55-5 [RN]
8B1QWR724A
More...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

282 [DBID]
102014; 5326088 [DBID]
83580_FLUKA [DBID]
AI3-50146 [DBID]
AIDS059773 [DBID]
AIDS-059773 [DBID]
BRN 0102014 [DBID]
C06539 [DBID]
Caswell No. 722A [DBID]
CCRIS 550 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      off-white crystalline powder OU Chemical Safety Data (No longer updated) More details

    • Stability:

      Stable, but darkens slowly in light. Combustible. Incompatible with strong acids, reducing agents, oxidizing agents. OU Chemical Safety Data (No longer updated) More details

    • Toxicity:

      Organic Compound; Amine; Ether; Ester; Drug; Adrenergic Uptake Inhibitor; Antipsychotic Agent; Antihypertensive Agent; Peripheral Adrenergic Inhibitor; Metabolite; Natural Compound; Adrenergic Antagonist Toxin, Toxin-Target Database T3D2713
      ORL-RAT LD50 420 mg kg-1, IPR-RAT LD50 44 mg kg-1, IVN-RAT LD50 15 mg kg-1, ORL-MUS LD50 200 mg kg-1, SCU-MUS LD50 52 mg kg-1, IPR-RBT LD50 7 mg kg-1, SCU-GPG LD50 65 mg kg-1, ORL-BWD LD50 100 mg kg-1 OU Chemical Safety Data (No longer updated) More details

    • Safety:

      C02AA02 Wikidata Q407841
      Safety glasses if handling powder. Do not exceed the stateddose if taking as medication. OU Chemical Safety Data (No longer updated) More details

    • Target Organs:

      Billiation inhibitor TargetMol T0791

    • Chemical Class:

      An alkaloid found in the roots of <ital>Rauwolfia serpentina</ital> and <ital>R. vomitoria</ital>. ChEBI CHEBI:28487
      An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28487, CHEBI:28487

    • Bio Activity:

      Binds the vesicular monoamine transporter (VMAT2) and inhibits transport of biogenic amines into adrenal chromaffin granules and synaptic vesicles. Causes depletion of biogenic amine stores. Antihyper tensive and antipsychotic. Tocris Bioscience 2742
      Binds the vesicular monoamine transporter (VMAT2) and inhibits transport of biogenic amines into adrenal chromaffin granules and synaptic vesicles. Causes depletion of biogenic amine stores. Antihypertensive and antipsychotic. Tocris Bioscience 2742
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB1895
      Inhibitor of vesicular monoamine transport Tocris Bioscience 2742
      Membrane Tranporter/Ion Channel MedChem Express HY-N0480
      Membrane Tranporter/Ion Channel; MedChem Express HY-N0480
      Metabolism TargetMol T0791
      Monoamine transporter MedChem Express HY-N0480
      Neurotransmitter Transporters Tocris Bioscience 2742
      Receptors & Transporters/Transporters/Monoamine/VMAT2 Hello Bio HB1895
      Reserpine (Serpalan) is an indole alkaloid antipsychotic and antihypertensive drug that irreversibly blocks the vesicular monoamine transporter (VMAT). MedChem Express
      Reserpine (Serpalan) is an indole alkaloid antipsychotic and antihypertensive drug that irreversibly blocks the vesicular monoamine transporter (VMAT).; Target: vesicular monoamine transporter (VMAT) ; Reserpine (Lannett's Serpalan) is an indole alkaloid antipsychotic and antihypertensive drug that has been used for the control of high blood pressure and for the relief of psychotic symptoms, although because of the development of better drugs for these purposes and because of its numerous side-effects, it is rarely used today. MedChem Express HY-N0480
      Reserpine (Serpalan) is an indole alkaloid antipsychotic and antihypertensive drug that irreversibly blocks the vesicular monoamine transporter (VMAT).;Target: vesicular monoamine transporter (VMAT) Reserpine (Lannett's Serpalan) is an indole alkaloid antipsychotic and antihypertensive drug that has been used for the control of high blood pressure and for the relief of psychotic symptoms, although because of the development of better drugs for these purposes and because of its numerous side-effects, it is rarely used today. The antihypertensive actions of reserpine are a result of its ability to deplete catecholamines (among other monoamine neurotransmitters) from peripheral sympathetic nerve endings. These substances are normally involved in controlling heart rate, force of cardiac contraction and peripheral vascular resistance.Reserpine irreversibly blocks the vesicular monoamine transporter (VMAT). This normally transports free intracellular norepinephrine, serotonin, and dopa MedChem Express HY-N0480
      SVAT;Bile salt export pump;MRP1 TargetMol T0791
      Transporters Tocris Bioscience 2742
      Vesicular monoamine re-uptake blocker Hello Bio HB1895
      Vesicular monoamine re-uptake blocker. Irreversibly binds VMAT2 to deplete synaptic monoamines. Produces depression-like effects and shows antipsychotic and antihypertensive effects. Hello Bio HB1895
      Vesicular Monoamine Transporters Tocris Bioscience 2742

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point: 700.1±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 102.5±3.0 kJ/mol
Flash Point: 377.2±32.9 °C
Index of Refraction: 1.620
Molar Refractivity: 160.9±0.4 cm3
#H bond acceptors: 11
#H bond donors: 1
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 2
ACD/LogP: 4.05
ACD/LogD (pH 5.5): 2.42
ACD/BCF (pH 5.5): 15.70
ACD/KOC (pH 5.5): 80.10
ACD/LogD (pH 7.4): 3.93
ACD/BCF (pH 7.4): 503.63
ACD/KOC (pH 7.4): 2569.35
Polar Surface Area: 118 Å2
Polarizability: 63.8±0.5 10-24cm3
Surface Tension: 59.9±5.0 dyne/cm
Molar Volume: 458.2±5.0 cm3

Click to predict properties on the Chemicalize site


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