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Palmatine

HCID 19009
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Grundinformationen

CAS
3486-67-7
Standard-SMILES
COc1cc2c(cc1OC)-c1cc3ccc(OC)c(OC)c3c[n+]1CC2
InChIKey
QUCQEUCGKKTEBI-UHFFFAOYSA-N
Summenformel
C21H22NO4+
Durchschnittliche Molmasse
352,41 g/mol
Monoisotopische Masse
352,1543346

Namen und Bezeichner

Bevorzugter Name
Palmatine
IUPAC
2,3,9,10-Tetramethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium
Englischer Name
Palmatine
Summenformel
C21H22NO4+
Molmasse
352.4

Namen und Synonyme

palmatinberbericinineo,o-dimethyldemethyleneberberine7,8,13,13a-tetrahydro-2,3,9,10-tetramethoxyberbinium7,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-berbiniug)quinolizinium,5,6-dihydro-2,3,9,10-tetramethoxy-dibenzo(2,3,9,10-TETRAMETHOXY-5,6-DIHYDRO-ISOQUINO[3,2-A]ISOQUINOLINYLIUMmatinePalatinePALMATINE

Datenbank-Bezeichner

CAS
3486-67-7
PubChem CID
19009
DTXSID
DTXSID9048065
ChEMBL
CHEMBL206106
ChEBI
CHEBI:16096
UNII
G50C034217
Nikkaji
J12.970D

Eigenschaften

Physikochemische Eigenschaften

Schmelzpunkt
205 °C · 205°C
storage temp.
2 · under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Aggregatzustand
Powder
Farbe
Yellow
Kosmetik-Inhaltsstoffe Funktionen
ANTIOXIDANT
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
InChIKey
QUCQEUCGKKTEBI-UHFFFAOYSA-N
SMILES
C12=CC3=C(C(OC)=C(OC)C=C3)C=[N+]1CCC1C=C(OC)C(OC)=CC2=1
LogP
-1.12 · -1.120 (est)
CAS Datenbank
3486 · 3486-67-7(CAS DataBase Reference)

Sicherheit und Regulatorisches

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Sicherheitsdaten

Toxizität
mouse,LD50,subcutaneous,135mg/kg (135mg/kg),Russian Pharmacology and Toxicology Vol. 31, Pg. 129, 1968.

Chemie und Industrie

Anwendungen · 2 Einträge

BeschreibungThis 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.

HistoryIn 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%

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