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

InChI

InChI=1S/C15H24N2O2/c18-14-7-1-6-13-12-5-3-9-17(19)8-2-4-11(15(12)17)10-16(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15?,17+/m0/s1

InChIKey

XVPBINOPNYFXID-LHDUFFHYSA-N

SMILES

[N@@+]12([O-])CCC[C@]3([H])C1[C@@]([H])([C@@]1([H])CCCC(=O)N1C3)CCC2

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)

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]¹⁹_D + 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.

Chemical Properties

Colorless lumpy crystals, easily soluble in chloroform, methanol, insoluble in petroleum ether, acetone, derived from Yam bean root, bitter ginseng.

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)

Ammothamnine(16837-52-8)Related Product Information

• Iron oxide
• NITRIC OXIDE
• Zinc oxide
• Magnesium oxide
• SophoraAlkaloidsTannate
• Propylene oxide
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• ETHYLENE OXIDE
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• Oxyresveratrol
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• OXYPEUCEDANIN
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• OXYSOPHOCARPINE
• (Diethoxymethyl)diphenylphosphine oxide
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