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Chemistry

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Also known as: 2086-83-1, Umbellatine, Berberin, Berbericine, Majarine, Thalsine
Molecular Formula
C20H18NO4+
Molecular Weight
336.4  g/mol
InChI Key
YBHILYKTIRIUTE-UHFFFAOYSA-N
FDA UNII
0I8Y3P32UF

Berberine
An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal.
1 2D Structure

Berberine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene
2.1.2 InChI
InChI=1S/C20H18NO4/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/q+1
2.1.3 InChI Key
YBHILYKTIRIUTE-UHFFFAOYSA-N
2.2 Other Identifiers
2.2.1 UNII
0I8Y3P32UF
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Umbellatine

2.3.2 Depositor-Supplied Synonyms

1. 2086-83-1

2. Umbellatine

3. Berberin

4. Berbericine

5. Majarine

6. Thalsine

7. Umbellatin

8. Berberone

9. Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy-

10. 0i8y3p32uf

11. Dtxsid9043857

12. Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-

13. 16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene

14. Chebi:16118

15. 9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium

16. 5,6-dihydro-9,10-dimethoxy-1,3-benzodioxolo(5,6-a)benzo(g)quinolizinium

17. 9,10-dimethoxy-5,6-dihydro(1,3)dioxolo(4,5-g)isoquino(3,2-a)isoquinolin-7-ium

18. 16,17-dimethoxy-5,7-dioxa-13$l^(5)-azapentacyclo(11.8.0.0^(2,10).0^(4,8).0^(15,20))henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium

19. 16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium

20. 16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo(11.8.0.02,10.04,8.015,20)henicosa-1(13),2,4(8),9,14,16,18,20-octaene

21. Refchem:5599

22. Dtxcid7023857

23. 218-229-1

24. 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium

25. Mfcd01175817

26. Berberal

27. St055798

28. 9,10-dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetrahydroberbinium

29. 5,6-dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium

30. Chembl12089

31. Gnf-pf-4545

32. Ber

33. Nsc646666

34. Ncgc00016526-02

35. Ncgc00016526-07

36. Cas-633-65-8

37. Berbinium

38. Berberine Dimer

39. Coptis Rhizome

40. Berberinechloride

41. C20h18no4

42. 5,6-dihydro-9,10-dimethoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium

43. Einecs 218-229-1

44. Umbellatine (6ci)

45. Brn 3570374

46. Spectrum_001110

47. Berbinium, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-, Chloride

48. Berberine [mi]

49. Prestwick0_000586

50. Prestwick1_000586

51. Prestwick2_000586

52. Prestwick3_000586

53. Spectrum2_000894

54. Spectrum3_000618

55. Spectrum4_000785

56. Spectrum5_001458

57. Berberine [vandf]

58. 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium

59. Berberine [mart.]

60. Upcmld-dp032

61. Ncimech_000354

62. Berberine [who-dd]

63. Unii-0i8y3p32uf

64. Schembl25632

65. Bspbio_000432

66. Bspbio_002156

67. Kbiogr_001230

68. Kbioss_001590

69. Cid_12456

70. Divk1c_000265

71. Inverted Exclamation Marky97%

72. Spbio_000708

73. Spbio_002651

74. Bpbio1_000476

75. Chembl295124

76. Megxp0_001923

77. Orb1302341

78. Schembl29354144

79. Schembl30153843

80. Upcmld-dp032:001

81. Acon1_001957

82. Bcbcmap01_000112

83. Gtpl11353

84. Kbio1_000265

85. Kbio2_001590

86. Kbio2_004158

87. Kbio2_006726

88. Kbio3_001656

89. Ninds_000265

90. 34md1011dm

91. Hms3561d13

92. Hms5086k15

93. Hy-n0716

94. Ac-117

95. Bbl029198

96. Bdbm50203126

97. Ccg-35898

98. S9046

99. Stk870320

100. 5,6-dihydro-9,10-dimethoxy-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium

101. Akos002141363

102. Db04115

103. Sdccgmls-0066718.p001

104. 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo-[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium

105. Berbinium, 7,8,13,13a-tetrahydro-9,10-dimethoxy-2,3-(methylenedioxy)-

106. Idi1_000265

107. Smp1_000298

108. Ncgc00016526-01

109. Ncgc00016526-03

110. Ncgc00016526-04

111. Ncgc00016526-05

112. Ncgc00016526-06

113. Ncgc00016526-08

114. Ncgc00016526-11

115. Ncgc00016526-13

116. Ncgc00016526-19

117. Ncgc00091896-03

118. Nci60_001050

119. Nci60_001224

120. Nci60_004319

121. Sy232626

122. Sbi-0051613.p002

123. Db-050153

124. Cs-0009734

125. Ns00009669

126. C00757

127. 086b831

128. 2,3-methylenedioxy-9,10-dimethoxy-protoberberine

129. Q176525

130. Berberine (constituent Of Goldenseal) [dsc]

131. Sr-01000711827-5

132. Brd-k14796088-003-06-0

133. Brd-k14796088-003-17-7

134. Brd-k14796088-003-25-0

135. Brd-k14796088-003-26-8

136. 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium

137. 9,10-dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium

138. Berbinium, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-

139. 3,4-dimethoxy-6,7-dihydro-[1,3]dioxolo[4,5-g]pyrido[2,1-a]isoquinolin-5-ylium

140. 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium

141. 9,10-dimethoxy-5,6-dihydro-2h-1,3-dioxoleno[4,5-g]isoquinolino[3,2-a]isoquinol Ine

142. 9,10-dimethoxy-5,6-dihydro-7lambda~5~-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline

143. Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy- (9ci)

144. 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium Chloride

145. 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; Chloride

146. Inchi=1/c20h18no4/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/q+

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 336.4 g/mol
Molecular Formula C20H18NO4+
XLogP33.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass Da
Monoisotopic Mass Da
Topological Polar Surface Area40.8
Heavy Atom Count25
Formal Charge1
Complexity488
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Mechanism of Action

This publication noted that berberine is an alkaloid from Hydrastis canadensis L., Chinese herb Huanglian, and many other plants. It is widely used in traditional Chinese medicine as an antimicrobial in the treatment of dysentery and infectious diarrhea. The authors describe the cardiovascular effects of berberine and its derivatives, tetrahydroberberine and 8-oxoberberine, e.g., berberine has positive inotropic, negative chronotropic, antiarrhythmic, and vasodilator properties. Some cardiovascular effects of berberine and its derivatives are attributed to the blockade of K+ channels (delayed rectifier and K(ATP)) and stimulation of Na+ -Ca(2+) exchanger. Also, berberine prolongs the duration of ventricular action potential. Its vasodilator activity has been attributed to multiple cellular mechanisms. The authors note that the cardiovascular effects of berberine suggest its possible clinical usefulness in the treatment of arrhythmias and/or heart failure.

doi:10.1111/j.1527-3466.2001.tb00068.x


Berberine, an isoquinoline alkaloid isolated from the Chinese herb Coptis chinensis and other Berberis plants, has a wide range of pharmacological properties. This publication notes the mechanisms of berberine's functions have been extensively explored, and that berberine: 1) can be used to treat many diseases, such as cancer and digestive, metabolic, cardiovascular, and neurological diseases, 2) has protective capacities in digestive diseases, 3) can inhibit toxins and bacteria, including Helicobacter pylori, protect the intestinal epithelial barrier from injury, and ameliorate liver injury, 4) inhibits the proliferation of various types of cancer cells and impedes invasion and metastasis, 5) improves the efficacy and safety of chemoradiotherapies, 6) regulates glycometabolism and lipid metabolism, improves energy expenditure, reduces body weight, and alleviates nonalcoholic fatty liver disease, 7) improves cardiovascular hemodynamics, suppresses ischemic arrhythmias, attenuates the development of atherosclerosis, and reduces hypertension, 8) shows potent neuroprotective effects, including antioxidative, antiapoptotic, and anti-ischemic, and 9) exerts protective effects against other diseases.

doi:10.1007/s11684-019-0724-6


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Berberine manufacturers, exporters & distributors 1

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API | Excipient name

Berberine

Synonyms

2086-83-1, Umbellatine, Berberin, Berbericine, Majarine, Thalsine

Cas Number

2086-83-1

Unique Ingredient Identifier (UNII)

0I8Y3P32UF

About Berberine

An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal.

Berberine Manufacturers

A Berberine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Berberine, including repackagers and relabelers. The FDA regulates Berberine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Berberine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Berberine Suppliers

A Berberine supplier is an individual or a company that provides Berberine active pharmaceutical ingredient (API) or Berberine finished formulations upon request. The Berberine suppliers may include Berberine API manufacturers, exporters, distributors and traders.

Berberine GMP

Berberine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Berberine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, and more, enabling you to easily find the right Berberine GMP manufacturer or Berberine GMP API supplier for your needs.

Berberine CoA

A Berberine CoA (Certificate of Analysis) is a formal document that attests to Berberine's compliance with Berberine specifications and serves as a tool for batch-level quality control.

Berberine CoA mostly includes findings from lab analyses of a specific batch. For each Berberine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Berberine may be tested according to a variety of international standards, such as European Pharmacopoeia (Berberine EP), Berberine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Berberine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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