3486-67-7

Basic information

• Product Name: Palmatine
• Synonyms: 7,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-berbiniu;7,8,13,13a-tetrahydro-2,3,9,10-tetramethoxyberbinium;berbericinine;g)quinolizinium,5,6-dihydro-2,3,9,10-tetramethoxy-dibenzo(;o,o-dimethyldemethyleneberberine;palmatin;PALMATINE;2,3,9,10-TETRAMETHOXY-5,6-DIHYDRO-ISOQUINO[3,2-A]ISOQUINOLINYLIUM
• CAS NO: 3486-67-7
• Molecular Formula: C21H22NO4+
• Molecular Weight: 352.4
• Product Categories: Miscellaneous Natural Products;Alkaloids;Natural Plant Extract;Plant extracts;API;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 3486-67-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 205°C
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Palmatine(CAS DataBase Reference)
• NIST Chemistry Reference: Palmatine(3486-67-7)
• EPA Substance Registry System: Palmatine(3486-67-7)

Safety Data

• Hazardous Substances Data: 3486-67-7(Hazardous Substances Data)

Usage

Description

This quaternary alkaloid occurs frequently in the Rhoeadales, being found in Cop tis japonica Mak. (Ranunculaceae); Berberis heteropoda Schrenk; B. vulgaris L. (Berberidaceae); Coscinium blumeatum Miers; Fibrauria chloroleuca Miers;Jatrorrhiza palmata (Lam.) Miers. (Menispermaceae); and Phellodendron amurense Rupr. (Rutcaeae). The base is usually obtained as the iodide dihydrate forming orange-yellow needles from H20, m.p. 241°C (dec.). Other salts that have been prepared include the chloride, green-yellow needles from H20, m.p. 205°C (dec.); nitrate, yellow needles, from H20, m.p. 239°C (dec.); perchlorate, m.p. 262°C (dec.); sulphate, m.p. 250°C; platinichloride, m.p. 236°C and the thiocyanate, m.p. 210°C (dec.). The alkaloid resembles berberine in yielding addition compounds with CHCl3 and Me2CO. On catalytic hydrogenation it gives tetrahydropalmatine, while on oxidation with alkaline KMn04 it furnishes corydaldine and hemipinic acid.

Physical properties

Appearance: yellow needle crystal, odorless, taste very bitter. Solubility: freely solu ble in hot water, sparingly soluble in water, slightly soluble in ethanol and chloroform, and almost insoluble in ether. Melting point: 205 °C. Relative density: 1.2 g/cm3 .

History

In the middle of the last century, Garrison health team of China and Honghe state hospital interviewed to explore the medicinal use of Huangteng in the screen edge of ethnic minority areas firstly and found its detoxification and anti-inflammatory effect of antibacterial. Then, it was promoted to be used in Yunnan province after the initial clinical validation. Palmatine on the market is mostly natural, which is mainly obtained from the extraction of dry rattan of Huangteng, one plant of Menispermaceae. The palmatine is abundant in the dry rattan of Huangteng with more than 2% palmatine chloride . It is an important part of technological research to obtain natural palmatine with high quality and high purityHonghe state in Yunnan province isolated and extracted palmatine from Huangteng firstly and then produced needle, tablets, ointment and topical solution, and other dosage forms for the treatment of various suppurative infections. It is now believed that the optimum conditions for the extraction of palmatine should be acid water decocting, firstly extracted from the rattan of Huangteng and then adjusted to pH 9-10, and NaCl salting out, which is obtained by precipitation purifica tion step by step, while ultrasonic can be used as an auxiliary means of extraction.The growth period of Huangteng is very long so that the extraction of natural palmatine cannot meet the market demand. Therefore, in order to alleviate the con tradiction of resources, researchers began to explore the method of chemical synthe sis of palmatine and its active derivatives in place of natural palmatine. At present, the improved synthetic method using berberine as raw material is the one with high yield, the total yield of which is 54%, and the purity of palmatine is 99%

Indications

Palmatine is included in the Pharmacopoeia of the People’s Republic of China (2015). As an antibacterial drug, palmatine is used to treat upper respiratory tract infections, tonsillitis, enteritis, dysentery, urinary tract infections, surgical and gynecological bacterial infections such as inflammation, and so on. Locally, it can treat conjunctivitis when dropping eyes and Candida albicans infection when used in vaginal topically

Pharmacology

Palmatine is a detoxification agent with a variety of pharmacological effects.Broad-spectrum antimicrobial antiviral effect: It can inhibit the activity of West Nile virus NS2B-NS3 protein, the Asian influenza A virus, dengue virus, and yellow fever virus. Also, it has an inhibitory effect on a variety of Gram-positive and Gram-negative bacteria, especially on fungi. Palmatine inhibits the proliferation of the Cordyceps epidermis and other 12 kinds of fungi to different degrees and has a good effect on shallow or deep infection caused by Candida albicans.Enhance the ability of leukocyte phagocytosis: 0.3 mL/100 g, once/day, a total of 10 days of intraperitoneal injection can enhance the macrophage phagocytosis func tion. Palmatine has a different degree of prophylactic or therapeutic effect on rat adjuvant arthritis when orally administered with suspension prepared by 0.5% car boxymethylcellulose for 9 days on dose of 0.5 mg/100 g. Palmatine can partially counter allergy caused by trichosanthin, and its anti-inflammatory effects may be related to the immune mechanism. Studies have shown that palmatine can improve cellular immunity, humoral immunity, and non-specific immune functionInsect resistance: Palmatine has a significant anti-Trichomonas vaginalis activity in vitro; the anti-vaginal trichomonas activity is equivalent to metronidazole, with seven different concentrations (20, 10, 5, 2.5, 1.25, 0.625, and 0.3125 μg/mL) and different times (2–48 h).Cardiovascular system: Palmatine can protect myocardial infarction, having a slight excitement on the frog heart and antiarrhythmic effect. It can also lower blood pressure when injecting intravenously anesthetized rabbits.In addition, the palmatine also showed an inhibition of central nervous function. However, the mechanism of pharmacological mechanism of brassinone is still not clear and need further studies

Clinical Use

Palmatine has an effect of detoxification; therefore, it is used mainly for gynecologi cal inflammation, such as acute and chronic pelvic inflammatory disease, acute and chronic annex inflammation, cervical erosion, endometritis, mycoplasma vaginitis, puerperal infection, bacillary dysentery, enteritis, urinary tract infection, surgical infection, conjunctivitis, respiratory tract infections, and so on.At present, palmatine has achieved some curative effect in combination therapy, but the small amount of adverse reactions of palmatine preparations in clinical treat ment cannot be ignored, such as allergic reactions and symptoms of catarr

References

Feist, Sandstede., Arch. Pharm., 256, 1 (1918) Spath, Quietensky., Ber., 58,2267 (1925) Haworth, Koepfli, Perkin., J. Chem. Soc., 548 (1927) Feist, Awe, Etzrodt., Chem. Zentr., I, 2374 (1935) Spath, Meinhard., Ber., 75,400 (1942)

InChI:InChI=1/C21H20NO4.H2O/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4;/h5-12H,1-4H3;1H2/q+1;

Upstream product

• 221527-72-6 7,8-dihydro-8-hydroxypalmatine 
• 131543-46-9 Glyoxal 
• 47355-66-8 N-(2,3-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethan-1-amine 
• 109806-78-2 N-(2,3-dimethoxybenzylidene)-2-(3,4-dimethoxyphenyl)ethanamine 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 162854-37-7 2,3,9,10-tetrahydroxyprotoberberine 
• 77-78-1 dimethyl sulfate 
• 26067-60-7 2,3,9,10-tetramethoxy-5,8-dihydro-6H-isoquinolino[3,2-α]isoquinoline 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 53811-50-0 6-bromo-2,3-dimethoxybenzaldehyde 
• 19716-59-7 8-oxypalmatine 

Downstream Products

• 3621-38-3 Jatrorrhizine 
• 16176-68-4 palmatrubine 

Relevant articles and documents

A 7,8-dihydro-8-hydroxypalmatine from Enantia chlorantha

7,8-dihydro-8-hydroxypalmatine, a novel protoberberine-type alkaloid, along with palmatine, has been isolated and characterized from an anti-HIV active extract from Enantia chlorantha. The structures of the two compounds were elucidated by spectroscopic analyses and from chemical evidence.

Method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control

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.

Compounds and Compositions for Modulating Lipid Levels and Methods of Preparing Same

The present technology relates to compounds of Formulas I-VI and methods of making and using such compounds. Methods of use include prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Compounds disclosed herein also increase HDL-C, lower total cholesterol, LDL-cholesterol, and triglycerides and increase hepatic LDL receptor expression, inhibit PCSK9 expression, and activate AMP-activated protein kinase.