Tetrahydroberberine

Modify Date: 2024-01-02 11:25:55

Tetrahydroberberine Structure
Tetrahydroberberine structure
Common Name Tetrahydroberberine
CAS Number 522-97-4 Molecular Weight 339.385
Density 1.3±0.1 g/cm3 Boiling Point 476.1±45.0 °C at 760 mmHg
Molecular Formula C20H21NO4 Melting Point N/A
MSDS N/A Flash Point 141.1±25.9 °C

 Use of Tetrahydroberberine


Tetrahydroberberine is an isoquinoline alkaloid isolated from corydalis tuber; has micromolar affinity for dopamine D(2) (pK(i) = 6.08) and 5-HT(1A) (pK(i) = 5.38) receptors but moderate to no affinity for other relevant serotonin receptors (5-HT(1B), 5-HT(1D), 5-HT(3), and 5-HT(4); pK(i) < 5.00).

 Names

Name canadine
Synonym More Synonyms

 Tetrahydroberberine Biological Activity

Description Tetrahydroberberine is an isoquinoline alkaloid isolated from corydalis tuber; has micromolar affinity for dopamine D(2) (pK(i) = 6.08) and 5-HT(1A) (pK(i) = 5.38) receptors but moderate to no affinity for other relevant serotonin receptors (5-HT(1B), 5-HT(1D), 5-HT(3), and 5-HT(4); pK(i) < 5.00).
Related Catalog
References

[1]. Lee TH, et al. Tetrahydroberberine, an isoquinoline alkaloid isolated from corydalis tuber, enhances gastrointestinal motor function. J Pharmacol Exp Ther. 2011 Sep;338(3):917-24.

[2]. Niwa M, et al. Dopaminergic unique affinity of tetrahydroberberine and l-tetrahydroberberine-d-camphor sulfonate. Pharmacology. 1991;43(6):329-36.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 476.1±45.0 °C at 760 mmHg
Molecular Formula C20H21NO4
Molecular Weight 339.385
Flash Point 141.1±25.9 °C
Exact Mass 339.147064
PSA 40.16000
LogP 3.83
Appearance of Characters solid | yellow
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.656
Storage condition 2-8°C
Water Solubility DMSO: >10 mg/mL, soluble

 Safety Information

Hazard Codes Xn: Harmful;
Risk Phrases R22
Safety Phrases 36
WGK Germany 3

 Synthetic Route

 Synonyms

l-Xanthopuccine
Hydroberberine
6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-
9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
9,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline
canadine
Tetrahydroberberine,THB
l-Canadine
(±)-Canadine
EINECS 208-338-2
5,6,13,13a-Tetrahydro-9,10-dimethoxy-2,3-(methylenedioxy)-8H-dibenzo[a,g]quinolizine
MFCD00067284
6H-1,3-Benzodioxolo[5,6-a]benzo[g]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-
dl-Canadine
UNII:V2SSH085X8
l-Tetrahydroberberine
5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine
THB
Tetrahydroberberine
5,6,13,13a-Tetrahydro-9,10-dimethoxy-2,3-(methylenedioxy)-8H-dibenzo(a,g)quinolizine
dl-Tetrahydroberberine
9,10-bis(methyloxy)-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
xanthopuccine
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