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Berberine Sulphate

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Chemistry

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Also known as: Berberine sulfate, 316-41-6, Berberin sulfate, Berberine sulfate (2:1), Berberal, Berberine sulfate trihydrate

Molecular Formula

C₄₀H₃₆N₂O₁₂S

Molecular Weight

768.8 g/mol

InChI Key

OJVABJMSSDUECT-UHFFFAOYSA-L

FDA UNII

FST3E667FF

1 2D Structure

Berberine Sulphate

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;sulfate

2.1.2 InChI

InChI=1S/2C20H18NO4.H2O4S/c2*1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2;1-5(2,3)4/h2*3-4,7-10H,5-6,11H2,1-2H3;(H2,1,2,3,4)/q2*+1;/p-2

2.1.3 InChI Key

OJVABJMSSDUECT-UHFFFAOYSA-L

2.1.4 Canonical SMILES

COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.[O-]S(=O)(=O)[O-]

2.2 Other Identifiers

2.2.1 UNII

FST3E667FF

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Berberine Sulfate

2. 316-41-6

3. Berberin Sulfate

4. Berberine Sulfate (2:1)

5. Berberal

6. Berberine Sulfate Trihydrate

7. Neutral Berberine Sulfate

8. 6190-33-6

9. Ai3-61947

10. Fst3e667ff

11. Berberine Sulfate Anhydrous

12. Erben

13. Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-, Sulfate (2:1)

14. 5,6-dihydro-9,10-dimethoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium Sulfate

15. Berberine Sulfate (van)

16. Nsc-5355

17. Hsdb 2170

18. Nsc 5355

19. Einecs 206-258-2

20. Unii-fst3e667ff

21. Berberinsulfat

22. 5,6-dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium Hemisulfate

23. Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydr0-9,10-dimethoxy-, Sulfate (2:1)

24. Berbinium, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-, Sulfate (2:1)

25. Schembl94112

26. Berberine Sulfate [hsdb]

27. Dtxsid70977452

28. Berberine Sulfate [who-dd]

29. Akos024319280

30. 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;sulfate

31. Bs-16855

32. B0451

33. Cs-0021605

34. D88653

35. Q27278174

36. 5,6-dihydro-9,10-dimethoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium Sulphate

37. 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium Sulfate(2:1)

38. 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-iumsulfate(2:1)

39. Bis(9,10-dimethoxy-5,6-dihydro-2h-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium) Sulfate

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₄₀H₃₆N₂O₁₂S
Molecular Weight	768.8 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	4
Exact Mass	768.19889576 g/mol
Monoisotopic Mass	768.19889576 g/mol
Topological Polar Surface Area	170 Å²
Heavy Atom Count	55
Formal Charge	0
Complexity	551
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Therapeutic Uses

EXPTL USE (VET): ORALLY ADMIN BERBERINE SULFATE (350-700 MG/KG) WAS EFFECTIVE IN TREATING CANDIDA ALBICANS INFECTIONS OF THE INTESTINE IN MICE.

MIRSKA I ET AL; ARCH IMMUNOL THER EXP; 20(6) 921 (1972)

EXPTL USE: DILATION OF HUMAN EYE PUPILS, TOPICAL ANESTHESIA &/OR FLUORESCENT STAINING OF CORNEAL EPITHELIAL DEFECTS &/OR FLUORESCENCE IN APPLANATION TONOMETRY, IS ACCOMPLISHED BY TOPICAL APPLICATION OF OPHTHALMIC SOLN OF HYDRASTIS COMPD SUCH AS BERBERINE.

MEDOW NB, GRECO JJ; US PATENT NUMBER 3943251 03/09/76

/PRC: FORMER USES/ BITTER STOMACHIC; ANTIBACTERIAL; ANTIMALARIAL; ANTIPYRETIC /BERBERINE/

The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 153

MILD LOCAL ANESTHETIC ON MUCOUS MEMBRANE. /BERBERINE/

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-161

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

...MAY BE ABSORBED THROUGH THE SKIN... /BERBERINE/

Sax, N.I. Dangerous Properties of Industrial Materials. 5th ed. New York: Van Nostrand Rheinhold, 1979., p. 412

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