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    Emetine

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    2D Structure
    Also known as: 14198-59-5, Mls000028478, Cephaeline methyl ether hydrochloride, Emetine (hydrochloride), Smr000058444, (2s,3r,11bs)-2-[[(1r)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1h-benzo[a]quinolizine;hydrochloride
    Molecular Formula
    C29H41ClN2O4
    Molecular Weight
    517.1  g/mol
    InChI Key
    HUEYSSLYFJVUIS-MRFSYGAJSA-N
    The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,3R,11bS)-2-[[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine;hydrochloride
    2.1.2 InChI
    InChI=1S/C29H40N2O4.ClH/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24;/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3;1H/t18-,21-,24+,25-;/m0./s1
    2.1.3 InChI Key
    HUEYSSLYFJVUIS-MRFSYGAJSA-N
    2.1.4 Canonical SMILES
    CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC.Cl
    2.1.5 Isomeric SMILES
    CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1C[C@@H]4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC.Cl
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Dihydrochloride, Emetine

    2. Emetine

    3. Emetine Dihydrochloride

    4. Hydrochloride, Emetine

    5. Ipecine

    6. Methylcephaeline

    2.2.2 Depositor-Supplied Synonyms

    1. 14198-59-5

    2. Mls000028478

    3. Cephaeline Methyl Ether Hydrochloride

    4. Emetine (hydrochloride)

    5. Smr000058444

    6. (2s,3r,11bs)-2-[[(1r)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1h-benzo[a]quinolizine;hydrochloride

    7. Nsc33669

    8. Nsc-33669

    9. Emetinal

    10. Erketin

    11. Encol

    12. Emetinehydrochloride

    13. Emetine, Hydrochloride

    14. Emetine Monohydrochloride

    15. Opera_id_1460

    16. Cephaeline Methyl Ether Hcl

    17. Schembl636599

    18. Chembl513000

    19. Niosh/jy5800000

    20. Hy-b1479c

    21. Dtxsid80424947

    22. Nsc752340

    23. S3233

    24. Akos024374935

    25. Nsc-752340

    26. Cs-0103259

    27. Jy58000000

    28. Emetan,7',10,11-tetramethoxy-, Dihydrochloride

    29. Q-100155

    30. 2h-benzo[a]quinolizine,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-[(1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolyl)methyl]-, Dihydrochloride

    2.3 Create Date
    2006-05-25
    3 Chemical and Physical Properties
    Molecular Weight 517.1 g/mol
    Molecular Formula C29H41ClN2O4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count7
    Exact Mass516.2754855 g/mol
    Monoisotopic Mass516.2754855 g/mol
    Topological Polar Surface Area52.2 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity679
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Amebicides

    Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal. (See all compounds classified as Amebicides.)

    Antinematodal Agents

    Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)

    Cathartics

    Agents that are used to stimulate evacuation of the bowels. (See all compounds classified as Cathartics.)

    Emetics

    Agents that cause vomiting. They may act directly on the gastrointestinal tract, bringing about emesis through local irritant effects, or indirectly, through their effects on the chemoreceptor trigger zone in the postremal area near the medulla. (See all compounds classified as Emetics.)

    Protein Synthesis Inhibitors

    Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)