3486-67-7 Usage
Description
Palmatine is a quaternary alkaloid commonly found in various plant families such as Ranunculaceae, Berberidaceae, Menispermaceae, and Rutaceae. It is known for its yellow needle crystal appearance, odorless, and very bitter taste. Palmatine is freely soluble in hot water, sparingly soluble in water, slightly soluble in ethanol and chloroform, and almost insoluble in ether. It has a melting point of 205°C and a relative density of 1.2 g/cm3.
Uses
1. Used in Pharmaceutical Industry:
Palmatine is used as a pharmaceutical compound for its various biological activities, including its resemblance to berberine in yielding addition compounds with CHCl3 and Me2CO. It is also used in the synthesis of tetrahydropalmatine through catalytic hydrogenation and corydaldine and hemipinic acid through oxidation with alkaline KMnO4.
2. Used in Traditional Medicine:
Palmatine is used as an active ingredient in traditional medicine, particularly in the treatment of various ailments due to its alkaloid properties and presence in several medicinal plants.
3. Used in Research and Development:
Palmatine is used as a research compound for studying its chemical properties, interactions with other compounds, and potential applications in drug development and pharmaceutical formulations.
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)
Check Digit Verification of cas no
The CAS Registry Mumber 3486-67-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,4,8 and 6 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 3486-67:
(6*3)+(5*4)+(4*8)+(3*6)+(2*6)+(1*7)=107
107 % 10 = 7
So 3486-67-7 is a valid CAS Registry Number.
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;
3486-67-7Relevant articles and documents
A 7,8-dihydro-8-hydroxypalmatine from Enantia chlorantha
Wafo, Pascal,Nyasse, Barthelemy,Fontaine, Catherine
, p. 279 - 281 (1999)
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
-
, (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.
Compounds and Compositions for Modulating Lipid Levels and Methods of Preparing Same
-
Page/Page column 70, (2011/02/15)
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.