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Berberine hydrochloride

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Berberine hydrochloride Basic information

Product Name:
Berberine hydrochloride
Synonyms:
  • TIMTEC-BB SBB006488
  • NATURAL YELLOW 18 CHLORIDE
  • NATURAL YELLOW 18
  • UMBELLATINE
  • BERBERINE HCL
  • BERBERINE HYDROCHLORIDE
  • BERBERIN HCL
  • BERBERINE HYDROCHLORIDE N-HYDRATE
CAS:
633-65-8
MF:
C20H18NO4.Cl
MW:
371.81
EINECS:
211-195-9
Product Categories:
  • plant extract
  • Natural Plant Extract
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • Aromatics
  • Heterocycles
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Plant extracts
  • standardized herbal extract
  • 633-65-8
Mol File:
633-65-8.mol
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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)
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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
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

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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 (Kd) = 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.

Berberine hydrochlorideSupplier

Shaanxi Pioneer Biotech CO., Ltd Gold
Tel
029-86107037-8019 15332321378
Email
sales@pioneerbiotech.com
Shanghai Zheyuan Chemical Co., Ltd. Gold
Tel
15921863060
Email
my_furongdi@163.com
Hubei Changao Pharmaceutical Co., Ltd Gold
Tel
027-87058617 13419515565
Email
195755151@qq.com
Chengdu Chenlv Herb Co., Ltd. Gold
Tel
028-88523492 15528171243
Email
chenrongpharma@126.com
Shanghai Jiaoze Industrial Co., LTD Gold
Tel
021-37318802 18616909727
Email
liangpanpan@sh-jiaoze.com