Amaryllidaceae alkaloids

Description:

Isoquinoline alkaloids with a skeleton deriving from lycorine, norbelladine, homolycorine, hemanthamine, crinine, tazettine, montanine, plicamine, galanthindole, galanthamine, gracilline, among others. Amaryllidaceae Alkaloids represent a large group of biogenetically related isoquinoline alkaloids that are found exclusively in plants belonging to this family of Amaryllidaceae. This group of alkaloids is also derived from two tyrosine units which combine, with loss of one carbon atom, to give a benzylphenylethylamine precursor unit, e.g. Norbelladine, which by various oxidative cyclisation processes, prominent among which are phenol oxidative coupling reactions, can give rise to the nine major skeletal groups.

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  1. Benzgalantamine
    CAS: 224169-27-1 PubChem CID: 44240142
    Out of Stock Item #: B1017456
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    IUPAC Name
    [(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-yl] benzoate
    SMILES
    CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)OC(=O)C5=CC=CC=C5
    InChIKey
    JKVNJTYHRABHIY-WXVUKLJWSA-N
    InChI
    1S/C24H25NO4/c1-25-13-12-24-11-10-18(28-23(26)16-6-4-3-5-7-16)14-20(24)29-22-19(27-2)9-8-17(15-25)21(22)24/h3-11,18,20H,12-15H2,1-2H3/t18-,20-,24-/m0/show more
  2. Pancratistatin
    CAS: 96203-70-2 PubChem CID: 441597
    Out of Stock Item #: P1060559
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    IUPAC Name
    (1R,2S,3S,4S,4aR,11bR)-1,2,3,4,7-pentahydroxy-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
    SMILES
    C1OC2=C(O1)C(=C3C(=C2)C4C(C(C(C(C4O)O)O)O)NC3=O)O
    InChIKey
    VREZDOWOLGNDPW-ALTGWBOUSA-N
    InChI
    1S/C14H15NO8/c16-8-5-3-1-4-13(23-2-22-4)9(17)6(3)14(21)15-7(5)10(18)12(20)11(8)19/h1,5,7-8,10-12,16-20H,2H2,(H,15,21)/t5-,7-,8-,10+,11+,12+/m1/s1
  3. SBE13 
    CAS: 775294-82-1 EC Number: 695-572-7 Formula: C24H27ClN2O4 Molecular Weight: 442.94
    Solid Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools. ≥98%
    In Stock Item #: S709314
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    IUPAC Name
    N-[[4-[(6-chloropyridin-3-yl)methoxy]-3-methoxyphenyl]methyl]-2-(3,4-dimethoxyphenyl)ethanamine
    SMILES
    COC1=C(C=C(C=C1)CCNCC2=CC(=C(C=C2)OCC3=CN=C(C=C3)Cl)OC)OC
    InChIKey
    XNPRQBVQOJZMMA-UHFFFAOYSA-N
    InChI
    1S/C24H27ClN2O4/c1-28-20-7-4-17(12-22(20)29-2)10-11-26-14-18-5-8-21(23(13-18)30-3)31-16-19-6-9-24(25)27-15-19/h4-9,12-13,15,26H,10-11,14,16H2,1-3H3
  4. Lycorenine
    CAS: 477-19-0 PubChem CID: 160472
    Analytical standard ? Analytical standard — certified-purity material for quantitative calibration. Use to prepare calibration standards and validate analytical methods. ≥98%(HPLC)
    Out of Stock Item #: L696045
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    IUPAC Name
    (5aR,7S,11bS,11cS)-9,10-dimethoxy-1-methyl-3,5,5a,7,11b,11c-hexahydro-2H-isochromeno[3,4-g]indol-7-ol
    SMILES
    CN1CCC2=CCC3C(C21)C4=CC(=C(C=C4C(O3)O)OC)OC
    InChIKey
    VHYYSQODIQWPDO-PILAGYSTSA-N
    InChI
    1S/C18H23NO4/c1-19-7-6-10-4-5-13-16(17(10)19)11-8-14(21-2)15(22-3)9-12(11)18(20)23-13/h4,8-9,13,16-18,20H,5-7H2,1-3H3/t13-,16-,17-,18+/m1/s1
  5. 4-bromo-5-({[2-(4-hydroxyphenyl)ethyl]amino}methyl)-2-methoxyphenol
    CAS: 179107-93-8 PubChem CID: 9429823 Formula: C16H18BrNO3 Molecular Weight: 352.22
    Out of Stock Item #: B669635
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    IUPAC Name
    4-bromo-5-[[2-(4-hydroxyphenyl)ethylamino]methyl]-2-methoxyphenol
    SMILES
    COC1=CC(Br)=C(CNCCC2=CC=C(O)C=C2)C=C1O
    InChIKey
    JBFKJIRYXUAQSW-UHFFFAOYSA-N
    InChI
    1S/C16H18BrNO3/c1-21-16-9-14(17)12(8-15(16)20)10-18-7-6-11-2-4-13(19)5-3-11/h2-5,8-9,18-20H,6-7,10H2,1H3
  6. Haemanthamine
    CAS: 466-75-1 PubChem CID: 441593 Formula: C17H19NO4 Molecular Weight: 301.34
    Out of Stock Item #: H649336
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    IUPAC Name
    (1S,13S,15S,18R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol
    SMILES
    COC1CC2C3(C=C1)C(CN2CC4=CC5=C(C=C34)OCO5)O
    InChIKey
    YGPRSGKVLATIHT-HSHDSVGOSA-N
    InChI
    1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3/t11-,15+,16+,17+/m1/s1
    Synonyms
    VBL6HZX2ZB | 3-Epicrinamine | 3-epi-Crinamine | SCHEMBL19915195 | NSC403140 | NSC-403140 | BDBM50221069 | 4a.beta.,11...
  7. ASN04450772
    Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.
    Out of Stock Item #: A607773
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    IUPAC Name
    4-amino-N'-(furan-2-ylmethyl)-N'-[1-(4-hydroxyphenyl)-2-[(4-methoxyphenyl)methylamino]-2-oxoethyl]-1,2-thiazole-3,5-dicarboxamide
    SMILES
    COc1ccc(cc1)CNC(=O)C(N(C(=O)c1snc(c1N)C(=O)N)Cc1ccco1)c1ccc(cc1)O
    InChIKey
    TVONKIFIPYRNRD-UHFFFAOYSA-N
    InChI
    1S/C26H25N5O6S/c1-36-18-10-4-15(5-11-18)13-29-25(34)22(16-6-8-17(32)9-7-16)31(14-19-3-2-12-37-19)26(35)23-20(27)21(24(28)33)30-38-23/h2-12,22,32H,13-1show more
    Synonyms
    ASN 04450772;ASN-04450772
  8. SBE 13 hydrochloride
    CAS: 1052532-15-6 EC Number: 694-771-6 PubChem CID: 11948807 Formula: C24H28Cl2N2O4 Molecular Weight: 479.4
    10mM in DMSO
    In Stock Item #: S420469
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    IUPAC Name
    N-[[4-[(6-chloropyridin-3-yl)methoxy]-3-methoxyphenyl]methyl]-2-(3,4-dimethoxyphenyl)ethanamine;hydrochloride
    SMILES
    COC1=C(C=C(C=C1)CCNCC2=CC(=C(C=C2)OCC3=CN=C(C=C3)Cl)OC)OC.Cl
    InChIKey
    QBGSVDJLQQXEGG-UHFFFAOYSA-N
    InChI
    1S/C24H27ClN2O4.ClH/c1-28-20-7-4-17(12-22(20)29-2)10-11-26-14-18-5-8-21(23(13-18)30-3)31-16-19-6-9-24(25)27-15-19;/h4-9,12-13,15,26H,10-11,14,16H2,1-3show more
    Synonyms
    AC-3511 | SBE-13 HCl;SBE13 HCl | N-{4-[(6-chloro-3-pyridinyl)methoxy]-3-methoxybenzyl}-N-[2-(3,4-dimethoxyphenyl)ethy...
  9. N-Desmethyl Galanthamine
    CAS: 41303-74-6 Formula: C16H19NO3 Molecular Weight: 273.33
    In Stock Item #: N334810
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    IUPAC Name
    (1S,12S,14R)-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol
    SMILES
    COC1=C2C3=C(CNCCC34C=CC(CC4O2)O)C=C1
    InChIKey
    AIXQQSTVOSFSMO-RBOXIYTFSA-N
    InChI
    1S/C16H19NO3/c1-19-12-3-2-10-9-17-7-6-16-5-4-11(18)8-13(16)20-15(12)14(10)16/h2-5,11,13,17-18H,6-9H2,1H3/t11-,13-,16-/m0/s1
    Synonyms
    2BPQ4IVQ21 | Stephaoxocanidine derivative | (4AS,6R,8AS)-3-METHOXY-5,6,9,10,11,12-HEXAHYDRO-4AH-(1)BENZOFURO(3A,3,2-E...
  10. Lycorine
    CAS: 476-28-8 Formula: C16H17NO4 Molecular Weight: 287.31
    In Stock Item #: L413074
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    Technical Identifiers
    IUPAC Name
    (1S,17S,18S,19S)-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraene-17,18-diol
    SMILES
    C1CN2CC3=CC4=C(C=C3C5C2C1=CC(C5O)O)OCO4
    InChIKey
    XGVJWXAYKUHDOO-DANNLKNASA-N
    InChI
    1S/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2/t11-,14-,15+,16+/m0/s1
    Synonyms
    Bunt-no-more | Bio2_000502 | EINECS 207-503-6 | Ethyl o-hydroxybenzoate | U-17312E | KBio2_000022 | HMS1791B04 | KBio...
  11. Lycorine
    CAS: 476-28-8 Formula: C16H17NO4 Molecular Weight: 287.31
    10mM in DMSO
    In Stock Item #: L424142
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    Technical Identifiers
    IUPAC Name
    (1S,17S,18S,19S)-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraene-17,18-diol
    SMILES
    C1CN2CC3=CC4=C(C=C3C5C2C1=CC(C5O)O)OCO4
    InChIKey
    XGVJWXAYKUHDOO-DANNLKNASA-N
    InChI
    1S/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2/t11-,14-,15+,16+/m0/s1
    Synonyms
    Bunt-no-more | Bio2_000502 | EINECS 207-503-6 | Ethyl o-hydroxybenzoate | U-17312E | KBio2_000022 | HMS1791B04 | KBio...
  12. Lycoramine
    CAS: 21133-52-8 Formula: C17H23NO3 Molecular Weight: 289.37
    In Stock Item #: L353976
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    Technical Identifiers
    IUPAC Name
    (1R,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9-trien-14-ol
    SMILES
    CN1CCC23CCC(CC2OC4=C(C=CC(=C34)C1)OC)O
    InChIKey
    GJRMHIXYLGOZSE-JDFRZJQESA-N
    InChI
    1S/C17H23NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-4,12,14,19H,5-10H2,1-2H3/t12-,14-,17-/m0/s1
    Synonyms
    (4AS,6S,8AR)-3-METHOXY-11-METHYL-5,6,7,8,9,10,11,12-OCTAHYDRO-4AH-(1)BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL | GALANTA...
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