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Home > Encyclopedia > BETA-AMANITIN

BETA-AMANITIN

BETA-AMANITIN structure

BETA-AMANITIN 

structure
  • CAS No:

    21150-22-1

  • Formula:

    C39H53N9O15S

  • Chemical Name:

    BETA-AMANITIN

  • Synonyms:

    BETA-AMANITIN;,12,17,18,19,20,21,22,23,23a-octadecahydro-29-sec-butyl-2,14-dihydroxy-21-(2,3;1-l-asparticacid-alpha-amaniti;8,20,23,24,27,30,33-octaoxo--dihydroxy-1-methylpropyl)-11-oxide;beta-amatoxin;B-amanitin from amanita phalloides;alpha-Amanitin, 1-l-aspartic acid-;beta-Amanitine

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

BETA-AMANITIN Basic Attributes

919.95

919.33800

244-244-8

Characteristics

394.30000

-2.21570

1.1725 (rough estimate)

300°

1.695

−20°C

Peritoneal-mouse LD50: 0.4 mg/kg; unknown-mouse LD50: 0.4 mg/kg

Flammable; burning produces toxic nitrogen oxides and sulfur oxide fumes

Safety Information

6.1(a)

UN 3462 6.1/PG 1

3

26/27/28

7-28-36/37/39-45

NJ8324000

T+

Warehouse ventilated, low temperature and dry

P260-P264-P280-P284-P302 + P350-P310

H300-H310-H330

REVIEW OF CHEMISTRY & TOXICOLOGY OF THE TOXINS OF AMANITA PHALLOIDES: WIELAND, WIELAND, PHARMACOL REV 11, 87-107 (1959); SEE ALSO FORTSCHR CHEM ORG NATURST 25, 214-250 (1967). /AMANITIN/

Toxicity

most toxic

...PHARMACOLOGICAL AGENTS.../HAVE/ BEEN REPORTED TO PROTECT MICE AGAINST LETHAL DOSES OF PHALLOTOXINS & AMATOXINS /INCLUDING THE AMANITINS/. THE LIST INCLUDES HIGH DOSES OF PENICILLIN, CHLORAMPHENICOL, PHENYLBUTAZONE, & MANY OTHERS... NONE OF THESE ANTIDOTES HAS RECEIVED AN ADEQUATE CLINICAL TRIAL & SO NONE CAN BE RECOMMENDED TODAY. /AMANITINS/

TOXIC GROUP FROM THE POISONOUS MUSHROOM AMANITA PHALLOIDES (FRENCH) SECR, AGARICACEAE. COMPRISED OF ALPHA-, BETA-, GAMMA-AMANITIN & AMANIN. /AMANITIN/|MANY IF NOT ALL OF THE FIVE RECOGNIZED.../TOXIC COMPONENTS IN AMANITA PHALLOIDES, INCLUDING THE AMANITINS/ ARE...PRESENT IN THE AMERICAN SUBSPECIES AMANITA VERNA (VIROSA), AMANITA BISPORIGERA, AMANITA TENUIFOLIA & PERHAPS AMANITA BRUNNESCENS. /AMANITINS/

Drug Information

5-6. 5= EXTREMELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 5-50 MG/KG, BETWEEN 7 DROPS & 1 TEASPOONFUL FOR 70 KG PERSON (150 LB). 6= SUPER TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) LESS THAN 5 MG/KG, A TASTE (LESS THAN 7 DROPS) FOR 70 KG PERSON (150 LB). /AMANITA TOXINS/

/IN COMPARISON WITH THE PHALLOTOXINS/...THE LONG DELAYED HEPATOTOXIC RESPONSE SEEN IN HUMAN POISONINGS...IS MORE LIKELY DUE TO...ALPHA-, BETA-, & GAMMA-AMANITIN, ESPECIALLY THE ALPHA COMPONENT. THESE SO-CALLED AMATOXINS...ARE MORE TOXIC THAN THE PHALLOTOXINS, &, UNLIKE THE LATTER, THEY DAMAGE THE NUCLEOLUS & LATER THE NUCLEUS OF LIVER CELLS.

HIGHLY TOXIC. CAUSES SALIVATION, VOMITING, BLOODY STOOLS, CYANOSIS, MUSCULAR TWITCHING, CONVULSIONS. CAN BE FATAL. /AMANITIN/|.../INHIBITS/ RNA POLYMERASE II &.../INTERFERES/ WITH THE SYNTHESIS OF MRNA. THE TOXINS DISRUPT HEPATIC CELL MEMBRANES & THE STRUCTURE OF THE ENDOPLASMIC RETICULUM. AMANITIN IS ALSO A DIRECTLY ACTING NEPHROTOXIN & CAUSES TUBULAR NECROSIS. /AMANITINS/|SYMPTOMS ARE SLOW IN ONSET, APPEARING 6 TO 24 HR AFTER INGESTION; THEY INCLUDE ABDOMINAL PAIN, HEMATURIA, & DIARRHEA. DEATH USUALLY RESULTS FROM HEPATIC OR RENAL FAILURE. /AMANITINS/|...LIVER INJURY IS USUALLY THE MAJOR LESION IN MAN. THERE APPEARS TO BE A PROMPT CESSATION OF BILE FLOW, A REDUCTION IN LIVER GLYCOGEN, HYPOGLYCEMIA WITH OR WITHOUT AN INITIAL PHASE OF HYPERGLYCEMIA, A FALL IN THE RNA CONTENT OF LIVER NUCLEI, & A FAILURE OF LIVER CELL PROTEIN SYNTHESIS, BUT WHETHER OR NOT ANY OF THESE EFFECTS IS THE PRIMARY LESION HAS NOT BEEN ESTABLISHED. /AMANITINS/

1-Asp-alpha-amanitin

BETA-AMANITIN Use and Manufacturing

Methods of Manufacturing

ISOLATION OF ALPHA- & BETA-AMANITIN: WIELAND, ANN 564, 152 (1949). PREPN OF ALPHA-AMANITIN FROM BETA-AMANITIN: WIELAND, BOEHRINGER, ANN 635, 178 (1960). STRUCTURE: WIELAND, PURE APPL CHEM 9, 145 (1964); WIELAND, GEBERT, ANN 700, 157 (1967). /AMANITIN/

Uses

β-Amanitin is a cyclic peptide found in several species of the Amanita genus, as well as other poisonous fungi. It inhibits RNA polymerase II and III but not RNA polymerase I or bacterial RNA polymerase, thus preventing mammalian protein synthesis. The biological activity of this toxin is similar to that of α-amanitin but differs structurally by the presence of a carboxyl group, which is useful for coupling reactions.

THE TOXIC PRINCIPLES OF AMANITA PHALLOIDES HAVE BEEN CHEMICALLY IDENTIFIED. ...TWO GROUPS ARE RECOGNIZED. THE PHALLOTOXINS (WHICH INCLUDES PHALLOIDIN) POSSESS A COMMON CYCLIC HEPTAPEPTIDE SKELETON...& /THE AMATOXINS: ALPHA-AMANITIN, BETA-AMANITIN, & GAMMA-AMANITIN/...POSSESS A COMMON OCTAPEPTIDE SKELETON.

AMATOXIN DETERMINATIONS BY HIGH-PERFORMANCE THIN-LAYER CHROMATOGRAPHY ON COMMERCIALLY AVAILABLE PLATES ARE PROPOSED. USING THESE PLATES, ALPHA-, BETA-, & GAMMA-AMANITIN CAN BE DETECTED IN EXTRACT ALIQUOTS CORRESPONDING TO GREATER THAN OR EQUAL TO 0.05-0.1 MG OF DRIED MUSHROOM TISSUE BY DIRECTLY SCANNING THE CHROMATOGRAM WITH A SPECTROPHOTOMETER. THE LIMIT OF DETECTION USING CINNAMALDEHYDE AS A CHROMOGENIC REAGENT IS 50 NG. BECAUSE OF ITS SENSITIVITY & RAPIDITY, THE METHOD HAS GREAT POTENTIAL FOR FORENSIC & CLINICAL ANALYSIS IN CASES OF MUSHROOM POISONING.

Computed Properties

Molecular Weight:920.0
XLogP3:-3.8
Hydrogen Bond Donor Count:13
Hydrogen Bond Acceptor Count:16
Rotatable Bond Count:7
Exact Mass:919.33818319
Monoisotopic Mass:919.33818319
Topological Polar Surface Area:394
Heavy Atom Count:64
Complexity:1840
Defined Atom Stereocenter Count:8
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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