Palmatine hydrochloride - ≥97% , CAS No.171869-95-7

CAS: 171869-95-7 Cat. No.: P110207 Molecular Weight: 387.86 EC Number: 630-670-5

GRADE & PURITY ≥97%

Synonyms

CAS-171869-95-7 | ZMR2H7M7PK | Tox21_200059 | AKOS015968461 | SCHEMBL3321462 | 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium;chloride;hydrate | Palmatine (chloride hydrate) | 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[3,2-a]isoq

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

CAS-171869-95-7 | ZMR2H7M7PK | Tox21_200059 | AKOS015968461 | SCHEMBL3321462 | 2, 3, 9, 10-tetramethoxy-5, 6-dihydroisoquinolino[2, 1-b]isoquinolin-7-ium;chloride;hydrate | Palmatine (chloride hydrate) | 2, 3, 9, 10-tetramethoxy-5, 6-dihydroisoquinolino[3, 2-a]isoq

Specifications & Purity

≥97%

Storage

Room temperature

Shipped In

Normal

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504768168
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504768168
• Canonical Smiles: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC.O.[Cl-]
• IUPAC Name: 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium;chloride;hydrate
• InChIKey: PIQNSCSNSSZUIT-UHFFFAOYSA-M
• INCHI: 1S/C21H22NO4.ClH.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;;/h5-6,9-12H,7-8H2,1-4H3;1H;1H2/q+1;;/p-1
• Isomeric SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC.O.[Cl-]
• WGK Germany: 3
• UN Number: 2811
• Molecular Weight: 387.86
• Reaxy-Rn: 25494309
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25494309&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Protoberberine alkaloids and derivatives

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Protoberberine alkaloids and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Protoberberine alkaloids and derivatives
• Alternative Parents: Isoquinolines and derivatives Anisoles Alkyl aryl ethers Pyridinium derivatives Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Organic chloride salts Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Protoberberine skeleton - Isoquinoline - Anisole - Alkyl aryl ether - Pyridine - Pyridinium - Benzenoid - Heteroaromatic compound - Organoheterocyclic compound - Azacycle - Ether - Organic salt - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organic chloride salt - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BCHE Tclin Butyrylcholinesterase (7174 Activities)

Discover Target: BCHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Flash Point(°F): 113 °C
• Flash Point(°C): 113°C
• Melt Point(°C): 206-207°C
• Molecular Weight: 405.900 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 405.134 Da
• Monoisotopic Mass: 405.134 Da
• Topological Polar Surface Area: 41.800 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 475.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 3

XLogP3

References

1. Wang Lei, Li Min, Zhu Cuiping, Qin Aiping, Wang Jinchun, Wei Xianni.  (2022)  The protective effect of Palmatine on depressive like behavior by modulating microglia polarization in LPS-induced mice.  NEUROCHEMICAL RESEARCH,  47  (10): (3178-3191).  [PMID:35917005] [10.1007/s11064-022-03672-3]

2. Yingxin Chen, Xiaotong Huang, Lu Li, Junxian Wu, Yongqi Guo, Yachao Yao, Lihua Zhou.  (2022)  Paper mill sludge-based carbon quantum dots as a specifically ratiometric fluorescent probe for the sensitive and selective detection of coptisine.  LUMINESCENCE,  37  (7): (1078-1086).  [PMID:35441456] [10.1002/bio.4260]

3. Zhen Li, Tan Wang, Xianbao Xu, Cong Wang, Daoliang Li.  (2021)  An “on–off” fluorescent probe based on cucurbit[7]uril for highly sensitive determination of ammonia nitrogen in aquaculture water.  Analytical Methods,  13  (36): (4090-4098).  [PMID:34554148] [10.1039/D1AY00981H]

4. Tian Xusheng, Zhang Yukun, Li Han, Li Yunfeng, Wang Ning, Zhang Wei, Ma Boyan.  (2020)  Palmatine ameliorates high fat diet induced impaired glucose tolerance.  BIOLOGICAL RESEARCH,  53  (1): (1-12).  [PMID:32928312] [10.1186/s40659-020-00308-0]

5. Chao Fan, Hao Tang, Licheng Wang, Yijing Li, Xusheng Wang, Shuai Wang, Xiaojing Liang.  (2020)  The preparation of a core–shell stationary phase by the in situ polymerization of a hydrophilic polymer on the surface of silica and its chromatographic performance.  NEW JOURNAL OF CHEMISTRY,  44  (27): (11704-11709).  [PMID:] [10.1039/D0NJ01197E]

6. Lei Wang, Jinchun Wang, Lei Han, Tong Chen.  (2024)  Palmatine Attenuated Lipopolysaccharide-Induced Acute Lung Injury by Inhibiting M1 Phenotype Macrophage Polarization via NAMPT/TLR2/CCR1 Signaling.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:38619332] [10.1021/acs.jafc.3c05597]

7. Zekun Zeng, Zhiwei Yang, Chenghao Li, Shujing Liu, Wei Wei, Ye Zhou, Simeng Wang, Mengjun Sui, Mengdan Li, Shumei Lin, Yangyang Cheng, Peng Hou.  (2024)  Advancing Cancer Immunotherapy through Engineering New PD-L1 Degraders: A Comprehensive Study from Small Molecules to PD-L1-Specific Peptide–Drug Conjugates.  JOURNAL OF MEDICINAL CHEMISTRY,      [PMID:39420825] [10.1021/acs.jmedchem.4c01652]