Berberine hydrochloride Chemical Properties

Melting point:

204-206 °C (dec.)

storage temp. 

Inert atmosphere,2-8°C

solubility 

methanol: soluble

form 

Yellow powder

Colour Index 

75160

color 

Yellow powder

Water Solubility 

SOLUBLE IN COLD WATER

BRN 

3836585

Stability:

Hygroscopic

InChI

InChI=1S/C20H18NO4.ClH/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2;/h3-4,7-10H,5-6,11H2,1-2H3;1H/q+1;/p-1

InChIKey

VKJGBAJNNALVAV-UHFFFAOYSA-M

SMILES

C12C=C3C(C(OC)=C(OC)C=C3)=C[N+]=1CCC1=CC3=C(OCO3)C=C21.[Cl-]

CAS DataBase Reference

633-65-8

EPA Substance Registry System

Berberine chloride (633-65-8)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-36-26

RIDADR 

1544

WGK Germany 

2

RTECS 

DR9866400

F 

3-10

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29349990

Toxicity

LD50 orl-rat: >15 g/kg KSRNAM 8,654,74

MSDS

• Language:English Provider: Natural Yellow 18
• Language:English Provider:SigmaAldrich

Berberine hydrochloride Usage And Synthesis

Chemical Properties

yellow crystalline powder

Uses

An isoqinoline alkaloid shown to have a chemopreventive property against colon tumor formation by inhibiting the enzyme cyclooxygenase-2 (cox-2) which is abundantly expressed in colon cancer cells. Al so inhibits Activator Protein 1 (AP-1), a transcription factor that plays a critical role in inflammation and carcinogenesis. Treatment with berberine potentially results in the reduced accumulation o f chemotherapeutic drugs.

Uses

An ingredient in some commercial eyewash products.

Uses

Berberine hydrochloride: antiarrhythmic, alpha2 agonist, anticonvulsant, antiinflammatory, antibacterial, antifungal, antitrypanosomal, antineoplastic, immunostimulant

Definition

Berberine Chloride is the orally bioavailable, hydrochloride salt form of berberine, a quaternary ammonium salt of an isoquinoline alkaloid and active component of various Chinese herbs, with potential antineoplastic, radiosensitizing, anti-inflammatory, anti-lipidemic and antidiabetic activities. Berberine is a naturally occurring yellow alkaloid in some plants. Berberine HCL is the native form combine with hydrogen chloride to make it more stable.

Definition

ChEBI: Berberine chloride (TN) is an organic molecular entity.

Biological Functions

Although the mechanisms of action through which berberine exerts its effects are not yet fully elucidated, upon administration this agent appears to suppress the activation of various proteins and/or modulate the expression of a variety of genes involved in tumorigenesis and inflammation, including, but not limited to transcription factor nuclear factor-kappa B (NF-kB), myeloid cell leukemia 1 (Mcl-1), B-cell lymphoma 2 (Bcl-2), B-cell lymphoma-extra large (Bcl-xl), cyclooxygenase (COX)-2, tumor necrosis factor (TNF), interleukin (IL)-6, IL-12, inducible nitric oxide synthase (iNOS), intercellular adhesion molecule-1 (ICAM-1), E-selectin, monocyte chemoattractant protein-1 (MCP-1), C-X-C motif chemokine 2 (CXCL2), cyclin D1, activator protein (AP-1), hypoxia-inducible factor 1 (HIF-1), signal transducer and activator of transcription 3 (STAT3), peroxisome proliferator-activated receptor (PPAR), arylamine N-acetyltransferase (NAT), and DNA topoisomerase I and II. The modulation of gene expression may induce cell cycle arrest and apoptosis, and inhibit cancer cell proliferation. In addition, berberine modulates lipid and glucose metabolism.

General Description

A highly potent and selective oxysterol EBI2 (GPR183) agonist (K_d) = 450 pM in a saturation binding assay, and EC₅₀ = 140 pM over EC₅₀ = 2.1 nM for its enantiomer, 7β,25-OHC, in a GTP-γS binding assay). Dose-dependently suppresses forskolin-induced cAMP accumulation in an EBI2-expressing SK-N-MC/CRE-β-galactosidase cell line (IC₅₀ = 2 nM), but not in control cells. Stimulates migration of LPS-activated spleen B-cells and anti-CD3/CD28-activated CD4⁺ T-cells in a dose-dependent manner. In addition, pharmacological inhibition of its biosynthesis in vivo by Clotrimazole, a CYP7B1inhibitor, promotes the migration of adoptively transferred pre-activated B cells to the T/B boundary, mimicking the phenotype of pre-activated B cells in EBI2-deficient mice.

Biochem/physiol Actions

An alkaloid with weak antibiotic properties. Substrate for MDR efflux pumps. Antimicrobial activities of berberine is potentiated by the MDR inhibitor 5′-methoxyhydnocarpin (5′-MHC). Berberine upregulates the expression of Pgp in hepatoma cells. Treatment with berberine potentially results in the reduced accumulation of chemotherapeutic drugs.

Safety Profile

Poison by intraperitoneal route.Slightly toxic by ingestion. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx andCl-.

Purification Methods

Berberine chloride crystallises from water to give the dihydrate. The anhydrous salt may be obtained by recrystallisation from EtOH/Et2O, wash the crystals with Et2O and dry them in a vacuum. The iodide has m 250o(dec) (from EtOH). [Perkin J Chem Soc 113 503 1918, Kametani et al. J Chem Soc(C) 2036 1969, Beilstein 27 I 515, 27 II 567.]

Clinical claims and research

People most commonly use berberine for diabetes, high levels of cholesterol or other fats in the blood, and high blood pressure. It is also used for burns, canker sores, liver disease, and many other conditions but there is no good scientific evidence to support many of these uses.

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