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Palmatine

HCID 19009
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
3486-67-7
Standard SMILES
COc1cc2c(cc1OC)-c1cc3ccc(OC)c(OC)c3c[n+]1CC2
InChIKey
QUCQEUCGKKTEBI-UHFFFAOYSA-N
Molecular formula
C21H22NO4+
Average molar mass
352.4 g/mol
Monoisotopic mass
352.15488318

Overview

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

Names & identifiers

Preferred name
Palmatine
IUPAC
2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium
English name
Palmatine
Molecular formula
C21H22NO4+
Molecular weight
352.4

Names & synonyms

Palmatine3486-67-7BerbericinineO,O-Dimethyldemethyleneberberine5,6-Dihydro-2,3,9,10-tetramethoxydibenzo[a,g]quinoliziniumpalmatine ionpalmatine cation7,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxyberbiniumDTXSID9048065G50C0342175,6-Dihydro-2,3,9,10-tetramethoxydibenzo(a,g)quinoliziniumCHEBI:16096
Show more names
7,8,13,13a-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]ISOQUINOLINYLIUMmatinePalatine
2,3,9,10-tetramethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium2,3,9,10-tetramethoxy-5,6-dihydroisoquino(3,2-a)isoquinoliniumRefChem:44890DTXCID0028036PalmatinBurasaineDibenzo[a,g]quinolizinium, 5,6-dihydro-2,3,9,10-tetramethoxy-2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium

Database identifiers

CAS
3486-67-7

Properties

Computed structural properties

XLogP
3.7
Topological polar surface area
40.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
26
Formal charge
1
Complexity
475

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift
Collision Cross Section183.2 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
205 °C · 205°C
storage temp.
2 · under inert gas (nitrogen or Argon) at 2-8°C
solubility
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form
Powder
color
Yellow
Cosmetics Ingredients Functions
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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

Toxicity
mouse,LD50,subcutaneous,135mg/kg (135mg/kg),Russian Pharmacology and Toxicology Vol. 31, Pg. 129, 1968.
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H317
Precautionary statements
P280

Chemistry & industry

Uses & manufacturing

Household ProductsInformation on 2 consumer products that contain Palmatine in the following categories is provided:
Applications · 2 items

DescriptionThis 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%

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
19009
DTXSID
DTXSID9048065
ChEMBL
CHEMBL206106
ChEBI
CHEBI:16096
UNII
G50C034217
Nikkaji
J12.970D
-1.12 · -1.120 (est)
CAS DataBase Reference
3486 · 3486-67-7(CAS DataBase Reference)
FDA UNII
50 C034217 · G50C034217
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H317
Precautionary statements
280 · P280
Toxicity
50 · mouse,LD50,subcutaneous,135mg/kg (135mg/kg),Russian Pharmacology and Toxicology Vol. 31, Pg. 129, 1968.

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
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Additional notes

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