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    Technical details about Retronecine, learn more about the structure, uses, toxicity, action, side effects and more

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    Retronecine

    REF. STANDARDS & IMPURITIES

    PharmaCompass

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    2D Structure
    1. Also known as: 480-85-3, Senecifolinene, Retronecin, (+)-retronecine, Ccris 5776, (1r,7ar)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-ol
    Molecular Formula
    C8H13NO2
    Molecular Weight
    155.19  g/mol
    InChI Key
    HJSJELVDQOXCHO-HTQZYQBOSA-N
    FDA UNII
    2P5723M6II
    retronecine is a natural product found in Senecio nebrodensis, Senecio squalidus, and other organisms with data available.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R,8R)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-ol
    2.1.2 InChI
    InChI=1S/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8-/m1/s1
    2.1.3 InChI Key
    HJSJELVDQOXCHO-HTQZYQBOSA-N
    2.1.4 Canonical SMILES
    C1CN2CC=C(C2C1O)CO
    2.1.5 Isomeric SMILES
    C1CN2CC=C([C@@H]2[C@@H]1O)CO
    2.2 Other Identifiers
    2.2.1 UNII
    2P5723M6II
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Heliotridine

    2. Retronecine, (1s-cis)-isomer

    3. Retronecine, Monohydrochloride, (1s-cis)-isomer

    4. Retronecine, Monohydrochloride, (1s-trans)-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. 480-85-3

    2. Senecifolinene

    3. Retronecin

    4. (+)-retronecine

    5. Ccris 5776

    6. (1r,7ar)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-ol

    7. (1r,8r)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1h-pyrrolizin-1-ol

    8. 2p5723m6ii

    9. (1r,7ar)-2,3,5,7a-tetrahydro-1-hydroxy-1h-pyrrolizine-7-methanol

    10. ( )-retronecine

    11. Hsdb 3567

    12. Unii-2p5723m6ii

    13. Retronecine [mi]

    14. 1h-pyrrolizine-7-methanol, 2,3,5,7a-beta-tetrahydro-1-alpha-hydroxy-

    15. Retronecine [hsdb]

    16. Schembl673883

    17. Chebi:8821

    18. Retronecine, Analytical Standard

    19. Dtxsid401020156

    20. Hy-n8419

    21. Zinc1996064

    22. Mfcd01684783

    23. Stl564628

    24. 1h-pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-1-hydroxy-, (1r-trans)-

    25. Akos003672869

    26. Cs-0144131

    27. C06177

    28. Q3933789

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 155.19 g/mol
    Molecular Formula C8H13NO2
    XLogP3-1.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count1
    Exact Mass155.094628657 g/mol
    Monoisotopic Mass155.094628657 g/mol
    Topological Polar Surface Area43.7 Ų
    Heavy Atom Count11
    Formal Charge0
    Complexity191
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Absorption, Distribution and Excretion

    Lactating rats dosed with (3)H-retronecine excreted within 3 hr approx 0.08% of the applied radioactivity in the milk mainly as yet not identified water soluble retronecine-derived metabolites and approx 0.02% as unchanged pyrrolizidine alkaloids (pas). Highest tissue levels of pas and metabolites, 6 hr after admin were found in liver and lungs.

    PMID:6623523 Luthy J et al; Toxicol Lett 17(3-4): 283 (1983)

    4.2 Metabolism/Metabolites

    Steric hindrance around the ester groups was the major factor inhibiting hydrolysis of pyrrolizidine alkaloids. Enzymic hydrolysis of retronecine di-isovalerate occurred primarily at the allylic 9-ester group. The results supported the view that a factor contributing to the lower hepatotoxicity of semisynthetic retronecine diesters compared with some natural pyrrolizidine alkaloids, is their greater susceptibility to detoxication by hydrolysis.

    Mattocks A; Toxicol Lett 14(1-2) 111 (1982)

    Levels of pyrrolic metabolites were measured in the livers of rats given some pyrrolizidine alkaloids and semisynthetic derivatives. Structural and chemical features favoring the formation of such metabolites were defined. The most important of these were steric hindrance or chemical properties giving resistance to ester hydrolysis; lipophilic character, allowing access to hepatic microsomal enzymes; a conformation favoring microsomal oxidation of the pyrroline ring in preference to n-oxidation.

    PMID:7226276 Mattocks A; Chem-Biol Interact 35(3): 301 (1981)

    Levels of pyrrolic metabolites were measured in the livers of rats given some pyrrolizidine alkaloids and semisynthetic derivatives. ... Heliotridine-based alkaloids gave more pyrrole than similar retronecine esters, heliotridine ditiglate gave less pyrrole than retronecine ditiglate because the former was more open to hydrolytic attack.

    PMID:7226276 Mattocks AR; Chem-Biol Interact 35(3): 301-310 (1981)

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