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Ammothamnine

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Ammothamnine Basic information

Product Name:
Ammothamnine
Synonyms:
  • OXYMATRINE
  • 1-oxide,(1-beta)-matridin-15-on
  • 1H,5H,10H-Dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one, dodecahydro-, 4-oxide, (4R,7aS,13aR,13bR,13cS)-
  • Ammothamnine Oxymatrine
  • Oxymatrine, 98%, from Sophora flavescens Aiton
  • (4R,7aS,13aR,13bR,13cS)-dodecahydro-4-oxide-1H,5H,10H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one
  • Oxymatrine 16837-52-8
  • matrine,1-oxide
CAS:
16837-52-8
MF:
C15H24N2O2
MW:
264.36
EINECS:
605-514-4
Product Categories:
  • Pyrazoles
  • Inhibitors
  • Plant extracts
  • chemical reagent
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Pharmaceutical material and intermeidates
  • Alkaloids
  • Natural Plant Extract
  • Plant extract
  • pharmaceutical intermediate
  • phytochemical
  • 16837-52-8
Mol File:
16837-52-8.mol
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Ammothamnine Chemical Properties

Melting point:
208℃
storage temp. 
Inert atmosphere,2-8°C
solubility 
methanol: soluble10mg/mL, clear, colorless
pka
4.87±0.20(Predicted)
form 
powder
color 
white to off-white
Stability:
Hygroscopic
InChIKey
XVPBINOPNYFXID-LHDUFFHYSA-N
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-20/22
Safety Statements 
24/25
WGK Germany 
3
RTECS 
OQ1770000
HS Code 
29399990
Hazardous Substances Data
16837-52-8(Hazardous Substances Data)
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Ammothamnine Usage And Synthesis

Description

An alkaloid from Sophora angustifolia var. flavescens S. and Z., the bas'e crystal_x0002_lizes as the monohydrate having the lower melting point given above. It is dextrorotatory with [α]19D + 47.7° (EtOH) and yields crystalline salts and derivatives: hydrobromide, m.p. 21SoC; aurichloride, m.p. 207°C (dec.); perchlorate, m.p. 240°C (dec.); picrate, m.p. 21SoC and the methochloride aurichloride, m.p. 18SoC (dec.). Ochiai and Ito have shown that it is formed by the action of hydrogen peroxide on Matrine (q.v.), indicating that its structure is matrine-N-oxide.

Description

Oxymatrine is a natural alkaloid isolated from the root of S. flavescens, an herb used in traditional Chinese herbal medicine. It has antiviral properties, inhibiting the replication of hepatitis B alone and in combination with lamivudine. Oxymatrine also prevents fibrosis in a number of organs including liver, at least in part by interfering with TGF-β signaling. This compound also induces apoptosis in certain cancer cells and ameliorates inflammation by impairing the translocation of nuclear factors-κB.

Uses

Oxymatrine is a an anti-tumor agent triggering apoptosis in human leukemia cells.

Uses

antifungal, hepatoprotectant

Definition

ChEBI: Ammothamnine is an alkaloid and a tertiary amine oxide.

References

Kondo et al., Arch. Pharm., 275,493 (1937)
Ochiai, Ito., Ber., 81,938 (1938)

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