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A1304

Sigma-Aldrich

β-Amanitin

from Amanita phalloides, ≥85% (HPLC), powder, RNA polymerase inhibitor

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About This Item

Empirical Formula (Hill Notation):
C39H53N9O15S
CAS Number:
21150-22-1
Molecular Weight:
919.95
EC Number:
244-244-8
MDL number:
MFCD00151212
UNSPSC Code:
12352200
PubChem Substance ID:
24890528
NACRES:
NA.77

product name

β-Amanitin from Amanita phalloides, ≥85% (HPLC)

Quality Level

200

Assay

≥85% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

CCC(C)C1NC(=O)CNC(=O)C2Cc3c([nH]c4cc(O)ccc34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(O)=O)C(=O)N5CC(O)CC5C(=O)NC(C(C)C(O)CO)C(=O)N2

InChI

1S/C39H53N9O15S/c1-4-16(2)31-36(60)41-11-28(53)42-25-15-64(63)38-21(20-6-5-18(50)7-22(20)45-38)9-23(33(57)40-12-29(54)46-31)43-37(61)32(17(3)27(52)14-49)47-35(59)26-8-19(51)13-48(26)39(62)24(10-30(55)56)44-34(25)58/h5-7,16-17,19,23-27,31-32,45,49-52H,4,8-15H2,1-3H3,(H,40,57)(H,41,60)(H,42,53)(H,43,61)(H,44,58)(H,46,54)(H,47,59)(H,55,56)

InChI key

IEQCUEXVAPAFMQ-UHFFFAOYSA-N

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General description

β-Amanitin belongs to the family of amatoxins. Amanitins are made of bicyclic octapeptides. β-Amanitin is composed of a carboxyl group and is acidic in nature.

Application

β-Amanitin from Amanita phalloides has been used:
  • as a calibration standard for the quantification of β-Amanitin using liquid chromatography-high resolution-mass spectrometry/mass spectrometry (LC-HR-MS/MS) method.
  • to determine its concentration in urine samples by capillary zone electrophoresis (CZE).
  • in the analysis of β-amanitin in toxic mushrooms by liquid chromatography coupled to time-of-flight mass spectrometry.

Biochem/physiol Actions

Toxic constituent of the mushroom, Amanita phalloides, inhibits eukaryotic RNA polymerase II and III, but not RNA polymerase I or bacterial RNA polymerase. Inhibits mammalian protein synthesis.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Certificates of Analysis (COA)

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U Bermbach et al.
Biochemistry, 29(29), 6839-6845 (1990-07-24)
Poly-L-ornithine with an average molecular weight of 32K was reacted with beta-amanitin hydroxysuccinimide ester to form an amide-linked toxin conjugate. Loading of the polymeric chain with amanitin was high, corresponding to up to 35% of the total weight. To this
Ramadan A Abuknesha et al.
Analytical and bioanalytical chemistry, 379(5-6), 853-860 (2004-06-29)
Polyclonal antisera to beta-amanitin were generated in sheep and used to construct a competitive ELISA for measurement of the toxin in human serum and urine. The assay had a detection limit of about 80 pg mL(-1), a dynamic range of
H H Maurer et al.
Journal of chromatography. B, Biomedical sciences and applications, 689(1), 81-89 (1997-02-07)
GC-MS is the method of choice for toxicological analysis of toxicants volatile in GC while non-volatile and/or thermally labile toxicants need LC-MS for their determination. Studies are presented on the toxicological detection of the amphetamine-like anorectic clobenzorex in urine by
Peng Li et al.
Gene, 532(1), 63-71 (2013-09-21)
Amanita exitialis is a lethal mushroom that was first discovered in Guangdong Province, China. The high content of amanitin in its basidiocarps makes it lethal to humans. To comprehensively characterize the A. exitialis transcriptome and analyze the Amanita toxins as
V A Robinson-Fuentes et al.
Journal of pharmaceutical and biomedical analysis, 47(4-5), 913-917 (2008-05-27)
Amanitins are toxins found in species of the mushroom genera Amanita, Lepiota and Galerina. Intoxication after ingestion of these mushrooms can be fatal with an estimated 20% of mortality rate. An early diagnosis is necessary in order to avoid invasive
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