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(±)-Tetrahydroberberine

(±)-Tetrahydroberberine structure

CAS No:
522-97-4
Formula:
C20H21NO4
Chemical Name:
(±)-Tetrahydroberberine
Synonyms:
6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine,5,8,13,13a-tetrahydro-9,10-dimethoxy-;Berbine,9,10-dimethoxy-2,3-(methylenedioxy)-;Berberine,9-deoxy-16,17-dihydro-;5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine;Berberine,tetrahydro-;Tetrahydroberberine;Xanthopuccine;Canadine;Tetrahydroumbellatine;(±)-Canadine;(±)-Tetrahydroberberine;dl-Tetrahydroberberine;dl-Canadine;NSC 36351;NSC 94918;Tetrahydroberineper;4979-14-0;26548-75-4;28111-09-3;29074-38-2
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

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).

Canadine is a berberine alkaloid that is 5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline substituted by methoxy groups at positions 9 and 10. It is a berberine alkaloid, an organic heteropentacyclic compound, an aromatic ether and an oxacycle.

(±)-Tetrahydroberberine Basic Attributes

Molecular Weight：

339.39

Exact Mass：

339.39

EC Number：

208-338-2

NSC Number：

94918|36351

DSSTox ID：

DTXSID5022724

Characteristics

PSA：

40.2

XLogP3：

3.83

Appearance：

yellow solid

Density：

1.3±0.1 g/cm3

Melting Point：

166.5 °C

Boiling Point：

476.1±45.0 °C at 760 mmHg

Flash Point：

141.1±25.9 °C

Refractive Index：

1.656

Water Solubility：

DMSO: >10 mg/mL, soluble

Storage Conditions：

2-8°C

Toxicity：

LD50 in mice (mg/kg): 940 orally; 790 s.c.; 100 i.v. (Sadritdinov, Sultanov)

Safety Information

wgk germany：

hazard class code：

safety instructions：

Marks：

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

Drug Information

MeSH：

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)|A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)|Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)

MeSH Entry Terms：

canadine

(±)-Tetrahydroberberine Use and Manufacturing

Canadine is a protoberberine alkaloidwhich potently block functional KATP channels natively expressed on midbrain dopamine neurons. Canadine is used for treatment of degenerative diseases or conditions associated with KATP channel signaling.

Computed Properties

Molecular Weight:339.4
XLogP3:3.1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:339.14705815
Monoisotopic Mass:339.14705815
Topological Polar Surface Area:40.2
Heavy Atom Count:25
Complexity:488
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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