Protoberberine alkaloids and derivatives

Description:

Alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Ancestors:

Organic compounds ⮕ Alkaloids and derivatives ⮕ Protoberberine alkaloids and derivatives

Popular Products

(S)-Cheilanthifoline
CAS: 483-44-3 Formula: C₁₉H₁₉NO₄ Molecular Weight: 325.400

Out of Stock Item #: S976978

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IUPAC Name

(13S)-17-methoxy-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-16-ol

SMILES

COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)O

InChIKey
FVXCQULKSPVRPK-HNNXBMFYSA-N

InChI

1S/C19H19NO4/c1-22-18-7-12-4-5-20-9-14-11(2-3-17-19(14)24-10-23-17)6-15(20)13(12)8-16(18)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1
Cavidine
CAS: 32728-75-9 Formula: C₂₁H₂₃NO₄ Molecular Weight: 353.4

Out of Stock Item #: C1322231

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IUPAC Name

(12S,13R)-16,17-dimethoxy-12-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaene

SMILES

C[C@@H]1[C@@H]2C3=CC(=C(C=C3CCN2CC4=C1C=CC5=C4OCO5)OC)OC

InChIKey
JTZZGWPIBBTYNE-FKIZINRSSA-N

InChI

1S/C21H23NO4/c1-12-14-4-5-17-21(26-11-25-17)16(14)10-22-7-6-13-8-18(23-2)19(24-3)9-15(13)20(12)22/h4-5,8-9,12,20H,6-7,10-11H2,1-3H3/t12-,20+/m0/s1
Corynoxidine
CAS: 57906-85-1 PubChem CID: 21589010

≥99%

Out of Stock Item #: C942565

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IUPAC Name

(7S,13aS)-2,3,9,10-tetramethoxy-7-oxido-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-7-ium

SMILES

COC1=C(C2=C(CC3C4=CC(=C(C=C4CC[N+]3(C2)[O-])OC)OC)C=C1)OC

InChIKey
QYEMUDHNCZHUKC-JTSKRJEESA-N

InChI

1S/C21H25NO5/c1-24-18-6-5-13-9-17-15-11-20(26-3)19(25-2)10-14(15)7-8-22(17,23)12-16(13)21(18)27-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-,22-/m0/s1
1-Methoxyberberium
CAS: 29133-52-6 PubChem CID: 3082297

Out of Stock Item #: M1278396

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IUPAC Name

3,16,17-trimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene;chloride

SMILES

COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=C(C5=C(C=C4CC3)OCO5)OC)OC.[Cl-]

InChIKey
IBMPNZBFNHPRMY-UHFFFAOYSA-M

InChI

1S/C21H20NO5.ClH/c1-23-16-5-4-12-8-15-18-13(6-7-22(15)10-14(12)19(16)24-2)9-17-20(21(18)25-3)27-11-26-17;/h4-5,8-10H,6-7,11H2,1-3H3;1H/q+1;/p-1
Palmatrubine
CAS: 16176-68-4 Formula: C₂₀H₂₀NO₄ Molecular Weight: 338.38

Solid Analytical standard ? ≥98% Derived from green cow bile

In Stock Item #: P724829

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IUPAC Name

2,3,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-9-ol

SMILES

COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)O

InChIKey
QBUIDYLGKMWNEA-UHFFFAOYSA-O

InChI

1S/C20H19NO4/c1-23-17-5-4-12-8-16-14-10-19(25-3)18(24-2)9-13(14)6-7-21(16)11-15(12)20(17)22/h4-5,8-11H,6-7H2,1-3H3/p+1

Synonyms
9-Hydroxy-2,3,10-trimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium
Discretamine
CAS: 605-34-5 PubChem CID: 22955 Formula: C₁₉H₂₁NO₄ Molecular Weight: 327.4

Out of Stock Item #: D693775

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IUPAC Name

3,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol

SMILES

COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)O

InChIKey
KNWVMRVOBAFFMH-UHFFFAOYSA-N

InChI

1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3
Corydalmine
CAS: 30413-84-4 Formula: C₂₀H₂₃NO₄ Molecular Weight: 341.40

Solid Moligand™ ? ≥98%

In Stock Item #: C696061

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IUPAC Name

(13aS)-2,3,9-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-10-ol

SMILES

COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)OC

InChIKey
DIHXHTWYVOYYDC-INIZCTEOSA-N

InChI

1S/C20H23NO4/c1-23-18-9-13-6-7-21-11-15-12(4-5-17(22)20(15)25-3)8-16(21)14(13)10-19(18)24-2/h4-5,9-10,16,22H,6-8,11H2,1-3H3/t16-/m0/s1

Synonyms
(-)-corydalmine | (S)-2,3,9-Trimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-10-ol | SCHEFFERINE | ...
Pseudopalmatine
CAS: 19716-66-6 PubChem CID: 644002 Formula: C₂₁H₂₂NO₄+ Molecular Weight: 352.4

≥98%

Out of Stock Item #: P698608

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IUPAC Name

2,3,10,11-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium

SMILES

COC1=C(C=C2C(=C1)CC[N+]3=CC4=CC(=C(C=C4C=C23)OC)OC)OC

InChIKey
CLFBXKHKECKSQM-UHFFFAOYSA-N

InChI

1S/C21H22NO4/c1-23-18-8-13-5-6-22-12-15-10-20(25-3)19(24-2)9-14(15)7-17(22)16(13)11-21(18)26-4/h7-12H,5-6H2,1-4H3/q+1
Jatrorrhizine Hydrochloride
CAS: 960383-96-4 PubChem CID: 21115138 Formula: C₂₀H₂₁ClNO₄+ Molecular Weight: 374.8

≥94%

Out of Stock Item #: J664400

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IUPAC Name

2,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-3-ol;hydrochloride

SMILES

COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC.Cl

InChIKey
JKMUUZMCSNHBAX-UHFFFAOYSA-O

InChI

1S/C20H19NO4.ClH/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3;/h4-5,8-11H,6-7H2,1-3H3;1H/p+1
Coptisine
CAS: 3486-66-6 Formula: C₁₉H₁₄NO₄ Molecular Weight: 320.32

Solid Moligand™ ? ≥98%

Out of Stock Item #: C664260

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IUPAC Name

5,7,17,19-tetraoxa-13-azoniahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(13),2,4(8),9,14,16(20),21,23-octaene

SMILES

C1C[N+]2=C(C=C3C=CC4=C(C3=C2)OCO4)C5=CC6=C(C=C51)OCO6

InChIKey
XYHOBCMEDLZUMP-UHFFFAOYSA-N

InChI

1S/C19H14NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,5-8H,3-4,9-10H2/q+1

Synonyms
6,7-Dihydro-[1,3]dioxolo[4',5':7,8]isoquinolino[3,2-a][1,3]dioxolo[4,5-g]isoquinolin-5-ium | 5,6-Dihydro-2,3:9,10-bis...
(R)-(+)-Corypalmine
CAS: 13063-54-2 Formula: C₂₀H₂₃NO₄ Molecular Weight: 341.4

≥98%

Out of Stock Item #: C664032

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IUPAC Name

(13aR)-2,9,10-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-3-ol

SMILES

COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)O)OC)C=C1)OC

InChIKey
BMCZTYDZHNTKPR-MRXNPFEDSA-N

InChI

1S/C20H23NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,9-10,16,22H,6-8,11H2,1-3H3/t16-/m1/s1
Tetrahydroepiberberine
CAS: 38853-67-7 PubChem CID: 5321317 Formula: C₂₀H₂₁NO₄ Molecular Weight: 339.39

≥99%

Out of Stock Item #: T650806

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IUPAC Name

16,17-dimethoxy-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaene

SMILES

COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)OC

InChIKey
UWEHVAXMSWXKRW-UHFFFAOYSA-N

InChI

1S/C20H21NO4/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3

Synonyms
C17898 | 16,17-dimethoxy-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaene | ...

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