2086-83-1 Usage
Description
Berberine is a quaternary ammonium salt derived from the protoberberine group of isoquinoline alkaloids. It is found in various plants such as Coptis chinensis (Rhizoma coptidis), Phellodendri Chinensis Cortex (huangbo), and Berberidis Radix (sankezhen). Berberine has been used in traditional Chinese medicine for thousands of years to treat intestinal bacterial infections and as an antipyretic analgesic. It is also known by various names in Chinese history, such as zhilian, chuanlian, weilian, jizhualian, shanglian, and xuanlian. Berberine is an odorless, yellow crystalline powder with a melting point of about 204-206°C and is heat labile.
Uses
Used in Pharmaceutical Industry:
Berberine is used as an antiseptic drug for treating intestinal infections caused by dysentery bacillus and E. coli. It is also known for its antibacterial and anti-inflammatory effects, with the highest content of the original alkaloid berberine class in Coptis chinensis.
Used in Chemical Industry:
Berberine is used as a chemical compound in the form of white to yellow crystals. It is insoluble in water but soluble in ether and alcohol. Salts of berberine, such as berberine bisulfate, berberine sulfate, and berberine hydrochloride, are also used in the chemical industry.
Brand Names:
Some of the brand names associated with Berberine include 3 P Maid, Berberal, Berberil, Detal, Kenmin-S, Kinosin S, Phelloverin A, Tangenin, and Thalsin.
History
Berberine is often used in the form of quaternary ammonium alkali. The solubility of berberine in water is lower, for example, berberine hydrochloride is 1:500, and berberine sulfate is 1:30. In 1926, berberine was first separated from bark of Zanthoxylum clava. Modern pharmacology study showed that berberine has defined structure and is a monomer of traditional Chinese medicine. Berberine can be obtained from many sources and is used in clinics, with reliable pharmacological effects and various and unique mechanisms.
At present, berberine can be synthesized by industrial biosynthesis. A series of derivatives can also be synthesized by structure modification, and the pharmacological activities of these derivatives have been tested.
World Health Organization (WHO)
Berberine, an alkaloid contained in many plants including
Berberis species, remains available in many tropical countries. Both traditional
herbal remedies and tablet formulations containing this substance have been used
in the treatment of gastrointestinal disease, and injectable preparations have been
claimed to be of value in the treatment of cutaneous leishmaniasis. The action
taken in Singapore relates to reports of jaundice, haemolytic anaemia and
kernicterus with brain damage in infants with G6PD deficiency who were exposed
either in utero or post-natally. Preparations for topical application are also
available in some countries. These have not been associated with reports of
systemic toxicity.
Hazard
Toxic via ingestion, inhalation, skin absorption.
Pharmacology
Berberine hydrochloride has extensive pharmacological effects, such as antibacterial, antiviral, anti-inflammatory, analgesic, anticancer, hyperglycemic, antilipidemic, antihypertension, anti-arrhythmic, anti-heart failure, and so on. Experimental study and clinical reports demonstrate that berberine has therapeutic effect on the endocrine system, circulatory system, nervous system, digestive system, and respiratory system and other diseases.
The clinical indication of berberine is intestinal bacterial infectious diarrhea, which is confirmed by years of clinical application. Berberine hydrochloride exerts effect on intestinal infection, eye conjunctivitis, and suppurative otitis media induced by Shigella dysenteriae, Escherichia coli, and Staphylococcus aureus and ameliorates gastritis and combined gastric and duodenal ulcers. Berberine hydrochloride also has curative effect on acute lung injury, pneumonia, and other respiratory diseases; peptic ulcer, colitis, and other digestive system diseases; pregnancy, urinary, and reproductive system infections; and other urinary tract and reproductive system diseases.
Clinical Use
Rhizoma coptidis, as the digestive tract disease medication, has a history of more
than 3000?years in China and India. Berberine, as a cathartic nonprescription drug,
is mainly used in the treatment of intestinal infection clinically. Clinical research
showed that berberine has hypoglycemic effect and has very good prevention and
treatment for diabetic patients with complications such as hypertension, hyperlipidemia, thrombosis, and inflammationThere are few oral side effects of berberine hydrochloride, accidentally appears
nausea, vomiting, rash, and fever, which can disappear after withdrawal of drug. In
patients with hemolytic anemia and lack of glucose-6-phosphate dehydrogenase, it
was forbidden to be used. Berberine if used intravenously is toxic, but is only suitable for oral drug delivery .
Safety Profile
An alkaloid poison by ingestionand subcutaneous routes. In humans, toxic doses lowerthe body temperature, increase peristalsis, and cause deathby central paralysis. Mutation data reported. Should carry apoison label. Should never be ingested without t
Purification Methods
Berberine crystallises from pet ether or ether as yellow needles or from H2O. [Beilstein 27 II 567, 27 III/IV 6539.]
Check Digit Verification of cas no
The CAS Registry Mumber 2086-83-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,8 and 6 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2086-83:
(6*2)+(5*0)+(4*8)+(3*6)+(2*8)+(1*3)=81
81 % 10 = 1
So 2086-83-1 is a valid CAS Registry Number.
InChI: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+1
2086-83-1Relevant articles and documents
(S)-TETRAHYDROPROTOBERINE OXIDASE THE FINAL ENZYME IN PROTOBERBERINE BIOSYNTHESIS
Amann, M.,Nagakura, N.,Zenk, M. H.
, p. 953 - 954 (1984)
A new flavin enzyme has been discovered which in the presence of oxygen catalyzes the oxidation of (S)-tetrahydroprotoberberines to protoberberines via the intermediate 7,14-dehydroberberinium.
Method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control
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, (2021/05/29)
The invention discloses a method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control. The method comprises the following steps: improving a substituent group of a high-iodine salt leaving group, generating pyridine alkyne under the action of relatively mild potassium tert-butoxide, and carrying out [4 + 2] cycloaddition reaction on the pyridine alkyne and diene to obtain polysubstituted isoquinoline ring precursor compounds. Ring opening and aromatization of the isoquinoline ring precursor are realized by developing a novel iridium-catalyzed cross-coupling method, polysubstituted isoquinoline ring compounds with connecting capacity are efficiently synthesized, and then the polysubstituted isoquinoline ring compounds are coupled with a high-activity polysubstituted cyclic boric acid to obtain 3-aryl isoquinoline high-grade intermediates. Through application of two different chemical principles, regulation and control of the 3-aryl isoquinoline high-grade intermediates are realized, and benzophenanthridine and protoberberine alkaloids are modularly, diversely and efficiently synthesized.
Berberine derivatives and their use
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Paragraph 0024; 0025; 0026; 0028, (2019/02/02)
The invention provides a compound shown in the formula (I) or a salt thereof and use of the compound and the salt, and R is C10-C18 alkyl or benzyl. The growth inhibition, growth inhibition, and invasion inhibition of the compound and the salt on malignant glioma cells are surprisingly better than that of a berberine derivative and berberine self. In addition, the compounds can be well positioned to mitochondria, so that the compounds can be used as a mitochondrial targeting drug delivery system.