Palmatine

Iupac Name：2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium

Molecular Weight：352.4

Modify Date.: 2022-11-29 11:21

Introduction:

Palmatine is an orally active and irreversible indoleamine 2,3-dioxygenase 1 (IDO-1) inhibitor. Palmatine can ameliorate DSS-induced colitis by mitigating colonic injury, preventing gut microbiota dysbiosis, and regulating tryptophan catabolism. Palmatine has the potential for colitis treatment[1].

Palmatine is a berberine alkaloid and an organic heterotetracyclic compound. It has a role as a plant metabolite.

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1. Names and Identifiers

: 1.1 Name; Palmatine; 1.2 Synonyms; 2,3,9,10-tetramethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium 2,3,9,10-Tetramethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolinium 5,6-Dihydro-2,3,9,10-tetramethoxy-dibenzo[a,g]quinolizinium 7,8,13,13a-tetradehydro-2,3,9,10-tetramethoxyberbinium 7,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-berbiniu 7,8,13,13a-tetrahydro-2,3,9,10-tetramethoxyberbinium berbericinine Burasaine Calystigine Common fibraurea stem Dibenzo[a,g]quinolizinium, 5,6-dihydro-2,3,9,10-tetramethoxy- FIBRAURETIN g)quinolizinium,5,6-dihydro-2,3,9,10-tetramethoxy-dibenzo( Hindarinine MFCD00221758 o,o-dimethyldemethyleneberberine palmatin Palmatine 2,3,9,10-Tetramethoxy-5,6-dihydro-isoquino[3,2-a]isoquinolinylium; View all

1.3 CAS No.: 3486-67-7

1.4 CID: 19009

1.5 Molecular Formula: C21H22NO4+ (isomer)

1.6 Inchi: InChI=1S/C21H22NO4/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/h5-6,9-12H,7-8H2,1-4H3/q+1

1.7 InChIkey: QUCQEUCGKKTEBI-UHFFFAOYSA-N

1.8 Canonical Smiles: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC

1.9 Isomers Smiles: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC

2. Properties

2.1 Melting point: 205°C

2.1 Boiling point: °Cat760mmHg

2.1 Flash Point: °C

2.1 Precise Quality: 352.15488318

2.1 PSA: 40.80000

2.1 logP: 3.38480

2.1 Color/Form: Yellow powder

2.2 StorageTemp: Inert atmosphere,2-8°C

3. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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4. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

5. Synthesis Route

3486-67-7Total: 5 Synthesis Route

86-51-1 137 Suppliers

3486-67-7 119 Suppliers

Literatures:
Bioorganic and Medicinal Chemistry Letters, , vol. 16, # 5 p. 1380 - 1383
Yield: null

120-20-7 251 Suppliers

3486-67-7 119 Suppliers

Literatures:
Bioorganic and Medicinal Chemistry Letters, , vol. 16, # 5 p. 1380 - 1383
Yield: null

221527-72-6

3486-67-7 119 Suppliers

Literatures:
Wafo, Pascal; Nyasse, Barthelemy; Fontaine, Catherine Phytochemistry, 1999 , vol. 50, # 2 p. 279 - 281
Yield: ~20%

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6. Precursor and Product

precursor:

47355-66-8

109806-78-2

221527-72-6

86-51-1

131543-46-9

120-20-7

product :

16176-68-4

7. Other Information

7.0 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.

7.1 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 .

7.2 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 purity
Honghe 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%; View all

7.3 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

7.4 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 function
Insect 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; View all

7.5 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

7.6 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)

7.7 Mesh Entry Terms: berbericinine

8. Computational chemical data

Molecular Weight: 352.4g/mol
Molecular Formula: C₂₁H₂₂NO₄+
Compound Is Canonicalized: True
XLogP3-AA: 3.7
Exact Mass: 352.15488318
Monoisotopic Mass: 352.15488318
Complexity: 475
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 40.8
Heavy Atom Count: 26
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB6OAAAAAAAAAAAAAAAAAAAAAAAAAA8eIEAAAAAAACx9AAAHgAAAAAADAzBngY+htMMFACgAzRnRACCiCAxIiAI2CA+7JgNJuLEsZuEMCpmwBnK6Aew0PMOoAABAAAYQABAAAIAADCAAAAAAAAAAA==

9. Question & Answer

What is the important role of Palmatine in the pharmaceutical field? Oct 07 2023
Palmatine is a natural compound that plays a significant role in the pharmaceutical field. It possesses unique pharmacological properties and wide-ranging applications. This article will delve into t..
What is Palmatine and its applications? Mar 15 2023
Palmatine is a hydrochloride alkaloid extracted from the plant Menispermum canadense, also known as yellow vine. It is also referred to as Big Palmatine, Palmatine Hydrochloride, African Menispermum A..
What is Palmatine and its wide range of applications? Mar 20 2021
Palmatine, also known as berberine hydrochloride, is a naturally derived plant medicine developed in China and is now included in the Chinese Pharmacopoeia. Extensive Applications Palmatine is a bioac..
What are the pharmacological effects and applications of Palmatine? Oct 23 2020
Background and overview[1][2] Yellow vine is the dried cane of the Fanggenaceae plant Fibraurea recisa, also known as celestial vine, Coptis chinensis, Golden Key, Garcinia chinensis, etc. It is mainl..

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