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Tetrahydroberberine

Names

[ CAS No. ]:
522-97-4

[ Name ]:
Tetrahydroberberine

[Synonym ]:
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

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]:

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor
Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor
Natural Products >> Alkaloid
Research Areas >> Neurological Disease

[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.


[Related Small Molecules]

CB-154 mesylate | SCH 23390 hydrochloride | Levodopa | Cabergoline | Thioridazine hydrochloride | Brexpiprazole | Domperidone | Trifluoperazine dihydrochloride | pimozide | Risperidone | SKF38393 HCl | Cariprazine | SERTINDOLE | Fluphenazine (dihydrochloride) | Nomifensine

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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds