palmatine

Names

[ Name ]:
palmatine

[Synonym ]:
Calystigine
7,8,13,13a-tetradehydro-2,3,9,10-tetramethoxyberbinium
MFCD00221758
palmatine
Burasaine
2,3,9,10-tetramethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium
2,3,9,10-Tetramethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolinium
palmatin
berbericinine
7,8,13,13a-tetrahydro-2,3,9,10-tetramethoxyberbinium
Dibenzo[a,g]quinolizinium, 5,6-dihydro-2,3,9,10-tetramethoxy-
o,o-dimethyldemethyleneberberine
Hindarinine
5,6-Dihydro-2,3,9,10-tetramethoxy-dibenzo[a,g]quinolizinium
Common fibraurea stem

Biological Activity

[Description]:

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].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Indoleamine 2,3-Dioxygenase (IDO)

Research Areas >> Inflammation/Immunology

[Target]

IDO1

[In Vitro]

Palmatine exhibits more potent IDO-1 inhibitory activity , which IC50 on rhIDO-1 is 157μM, and on HEK 293-hIDO-1 is 3 μM[1].

[In Vivo]

Palmatine (oral administration; 50 or 100 mg/kg, 7 days) has less distortion of epithelium, and fewer infiltrations of inflammatory cells, resulting in significantly lower histopathological scores, it also significantly suppresses the colonic MPO activity[1]. Animal Model: DSS- induced Colitis BALB/c mice model[1] Dosage: 50 or 100 mg/kg; 7 days Administration: Oral administration Result: Ameliorated DSS-induced colitis and prevented infiltration of inflammatory cells.

[References]

[1]. Zhang XJ, et al. Palmatine ameliorated murine colitis by suppressing tryptophan metabolism and regulating gut microbiota.Pharmacol Res. 2018 Nov;137:34-46.

Chemical & Physical Properties

[ Melting Point ]:
205ºC

[ Molecular Formula ]:
C₂₁H₂₂NO₄+

[ Molecular Weight ]:
352.403

[ Exact Mass ]:
352.154327

[ PSA ]:
40.80000

[ LogP ]:
-1.12

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DR9890000

CHEMICAL NAME :: Berbinium, 7,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-

CAS REGISTRY NUMBER :: 3486-67-7

BEILSTEIN REFERENCE NO. :: 1555498

LAST UPDATED :: 199712

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C21-H22-N-O4

MOLECULAR WEIGHT :: 352.44

WISWESSER LINE NOTATION :: T D6 B666 KN&TT&J GO1 HO1 PO1 QO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 135 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: RPTOAN Russian Pharmacology and Toxicology (English Translation). Translation of FATOAO. (Euromed Pub., 33, Woodlands Rd., Surbiton, Surrey, UK) V.30- 1967- Volume(issue)/page/year: 31,129,1968

Safety Information

[ Hazard Codes ]:
Xi

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%