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    Rescinnamine

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    PharmaCompass
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    2D Structure
    Also known as: Recinnamine, Reserpinene, Trimethoxycinnamoyl methyl reserpate, Methyl (1r,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate, Ncgc00016787-01, 3,4,5-trimethoxycinnamoyl methyl reserpate
    Molecular Formula
    C35H42N2O9
    Molecular Weight
    634.7  g/mol
    InChI Key
    SZLZWPPUNLXJEA-LAFLMMDJSA-N
    Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is an alkaloid obtained from Rauwolfia serpentina and other species of Rauwolfia.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
    2.1.2 InChI
    InChI=1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/t20-,24+,26-,29-,31+,34+/m1/s1
    2.1.3 InChI Key
    SZLZWPPUNLXJEA-LAFLMMDJSA-N
    2.1.4 Canonical SMILES
    COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C=CC6=CC(=C(C(=C6)OC)OC)OC
    2.1.5 Isomeric SMILES
    CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C=CC6=CC(=C(C(=C6)OC)OC)OC
    2.2 Synonyms
    2.2.1 Depositor-Supplied Synonyms

    1. Recinnamine

    2. Reserpinene

    3. Trimethoxycinnamoyl Methyl Reserpate

    4. Methyl (1r,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

    5. Ncgc00016787-01

    6. 3,4,5-trimethoxycinnamoyl Methyl Reserpate

    7. Cas-24815-24-5

    8. Prestwick0_000568

    9. Prestwick1_000568

    10. Dsstox_cid_3554

    11. Dsstox_rid_77079

    12. Dsstox_gsid_23554

    13. Spbio_002575

    14. Chembl3182071

    15. Tox21_110611

    16. Db01180

    17. Q27164665

    18. (1r,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-[1-oxo-3-(3,4,5-trimethoxyphenyl)prop-2-enoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic Acid Methyl Ester

    2.3 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 634.7 g/mol
    Molecular Formula C35H42N2O9
    XLogP34.5
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count11
    Exact Mass634.28903092 g/mol
    Monoisotopic Mass634.28903092 g/mol
    Topological Polar Surface Area118 Ų
    Heavy Atom Count46
    Formal Charge0
    Complexity1080
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count1
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of hypertension.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Used to treat hypertension. Rescinnamine inhibits angiotensin-converting enzyme. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin II. Angiotensin II also stimulates aldosterone secretion by the adrenal cortex and general vasoconstriction, both of which lead to increases vascular resistance. By inhibiting angiotensin II, aldosterone reabsorption is decreased as well as vasoconstriction. This combined effect serves to decrease blood pressure.

    5.2 Mechanism of Action

    Rescinnamine Binds to and inhibits the angiotensin converting enzyme. Rescinnamine competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Inhibition of ACE results in decreased plasma angiotensin II. As angiotensin II is a vasoconstrictor and a negative-feedback mediator for renin activity, lower concentrations result in a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms, which leads to decreased vasopressor activity and to decreased aldosterone secretion.