Palmatine

Base Information

• Chemical Name: Palmatine
• CAS No.: 3486-67-7
• Molecular Formula: C21H22NO4
• Molecular Weight: 352.41
• Hs Code.: 2933990090
• UNII: G50C034217
• DSSTox Substance ID: DTXSID9048065
• Nikkaji Number: J12.970D
• Wikipedia: Palmatine
• Wikidata: Q6634283
• Metabolomics Workbench ID: 50375
• ChEMBL ID: CHEMBL206106
• Mol file: 3486-67-7.mol

Synonyms:berbericinine;berbinium, 7,8,13,13a-tetradehydro-2,3,9,10-tetramethoxy-, chloride;berbinium, 7,8,13,13a-tetradehydro-2,3,9,10-tetramethoxy-, iodide;dibenzo(a,g)quinolizinium, 5,6-dihydro-2,3,9,10-tetramethoxy-, chloride (1:1);dibenzo(a,g)quinolizinium, 5,6-dihydro-2,3,9,10-tetramethoxy-, hydroxide (1:1);o,o-dimethyldemethyleneberberine;palmatine;palmatine cation;palmatine chloride;palmatine hydrochloride;palmatine hydroxide;palmatine iodide;palmatine ion;palmatine sulfate;palmatinium hydroxide;palmitine hydroxide

Chemical Property of Palmatine

Chemical Property:

• Melting Point: 205 °C
• PSA: 40.80000
• LogP: 3.38480
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 352.15488318
• Heavy Atom Count: 26
• Complexity: 475

Purity/Quality:

99% ^*data from raw suppliers

Palmatine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC
• 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 .
• 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
• 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

Technology Process of Palmatine

There total 18 articles about Palmatine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

2-[2-(6,7-dimethoxyisoquinolin-3-yl)-4,5-dimethoxyphenyl]ethanol → palmatine (3486-67-7)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 6h;

Reference yield: 82.0%

2,3,9,10-tetrahydroxyprotoberberine (162854-37-7) + dimethyl sulfate (77-78-1) → palmatine (3486-67-7)

Guidance literature:

2,3,9,10-tetrahydroxyprotoberberine; With potassium carbonate; In acetone; at 20 ℃; for 0.333333h;

dimethyl sulfate; In acetone; Reflux;

Reference yield: 60.0%

Glyoxal (131543-46-9,107-22-2) + N-(2,3-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethan-1-amine (47355-66-8) → palmatine (3486-67-7)

Guidance literature:

Glyoxal; N-(2,3-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethylamine; With copper(II) sulfate; acetic acid; sodium chloride; at 50 ℃; for 0.5h;

With acetic acid; at 85 ℃; for 6h;

DOI:10.1016/j.bmcl.2005.11.045

upstream raw materials:

7,8-dihydro-8-hydroxypalmatine

Glyoxal

N-(2,3-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethan-1-amine

N-(2,3-dimethoxybenzylidene)-2-(3,4-dimethoxyphenyl)ethanamine

Downstream raw materials:

palmatrubine

Jatrorrhizine

Refernces

• 1、 Doskotch et al.. "". . p. 3253. Retrieved 1967.
• 2、 Zhou, Shiqiang,Tong, Rongbiao. "A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps". supporting information. p. 7084 - 7089. Retrieved 2016/05/19.
• 3、 Bian, Xiaoli,He, Langchong,Yang, Guangde. "Synthesis and antihyperglycemic evaluation of various protoberberine derivatives". . p. 1380 - 1383. Retrieved 2007/10/03.