Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > ALPHA-AMANITIN

ALPHA-AMANITIN

ALPHA-AMANITIN structure

ALPHA-AMANITIN 

structure
  • CAS No:

    23109-05-9

  • Formula:

    C39H54N10O14S

  • Chemical Name:

    ALPHA-AMANITIN

  • Synonyms:

    Aids004473;Aids-004473;AMANITIN, a-(RG);AMANITIN, a-(RG)(CALL);cyclo[L-Asparaginyl-4-hydroxy-L-proly-(R-4,5-dihydroxy-L-isoleucyl-6-hydroxy-2-mercapto-L-tryptophylglycyl-L-isoleucylglycyl-L-cysteinyl]cyclic(4-8)-sulfide(R)-S-oxide;alpha-AMantine, froM AManita Phalloides;AMANITIN, A-;ALPHA-AMANITIN

  • Categories:

    Natural Products  >  Alkaloids

Description

alpha-Amanitin is the principal toxin of several deadly poisonous mushrooms, exerting its toxic function by inhibiting RNA-polymerase II.


A cyclic octapeptide with a thioether bridge between the cystine and tryptophan. It inhibits RNA POLYMERASE II. Poisoning may require LIVER TRANSPLANTATION.

ALPHA-AMANITIN Basic Attributes

918.97

918.35400

245-432-2

DTXSID1036709

NEEDLES FROM METHANOL

Characteristics

400.09000

white to light yellow powder

1.57 g/cm3

254-255 °C(lit.)

1622.2ºC at 760 mmHg

934.9ºC

1.694

H2O: 1.0 mg/mL

−20°C

Peritoneal-mouse LD50: 0.1 mg/kg

Flammable; burning produces toxic nitrogen oxides and sulfur oxide fumes

D20 +191°

Safety Information

I

6.1(a)

UN 3462 6.1/PG 2

3

26/27/28-33-26/28

36/37/39-45-36/37-28

BD6195000

T+

Warehouse ventilated, low temperature and dry

P260-P264-P280-P284-P301 + P310-P302 + P350

H300-H310-H330-H373

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/

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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/|RNA SYNTHESIS IN HELA NUCLEI WAS STIMULATED BY METHYLMERCURY. THIS STIMULATION IS SPECIFIC FOR ALPHA-AMANITIN-SENSITIVE RNA SYNTHESIS (CATALYZED BY RNA POLYMERASE); IN CONTRAST, ALPHA-AMANITIN-RESISTANT SYNTHESIS (CATALYZED BY RNA POLYMERASES I & III) WAS INHIBITED.

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/

Substances which, when ingested, inhaled, or absorbed, or when applied to, injected into, or developed within the body in relatively small amounts may, by their chemical action, cause damage to structure or disturbance of function. (From Dorland, 27th ed) (See all compounds classified as Poisons.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)

/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.

EXPTL USE: THE SORBENT CAPACITY OF UNCOATED CHARCOAL COLUMN (DETOXYL 2, SORIN BIOMEDICA) ON ALPHA-AMANITIN WAS STUDIED BY ADDING KNOWN AMOUNTS TO FRESH HUMAN BLOOD, WHICH WAS RECIRCULATED THROUGH A CLINICAL HEMOPERFUSION CIRCUIT OVER A PERIOD OF 30 MINUTES. SUITABLE AMOUNTS OF ALPHA-AMANITIN WERE PRESENT IN THE ACID ELUATES, SHOWING AN ADSORPTION OPTIMUM FOR BLOOD CONCN RANGING FROM 50 TO 200 NG/ML. THE CLINICAL USEFULNESS OF CHARCOAL HEMOPERFUSION IN AMANITA PHALLOIDES POISONING IS DISCUSSED.

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/|MAN IS SAID TO BE EVEN MORE SUSCEPTIBLE /THAN LAB RODENTS WHOSE MEAN LETHAL DOSE OF ALPHA-AMANITIN IS ONLY 0.1 MG/KG/. A SINGLE SPECIMEN OF AMANITA PHALLOIDES MAY CONTAIN MORE THAN ENOUGH OF THIS CONSTITUENT TO KILL A MAN.

Amanitin|Alpha Amanitin

ALPHA-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/

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.

A REVERSED-PHASE HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY METHOD FOR THE QUANTITATIVE DETERMINATION OF ALPHA-AMANITIN IN SERUM OF POISONED PATIENTS IS DESCRIBED WITH DETECTION OF 25 NG ALPHA-AMANITIN/ML OF SERUM. THE TECHNIQUE IS A USEFUL TOOL TO DETERMINE THE SEVERITY OF AMANITA PHALLOIDES INTOXICATION DURING THE 1ST 24 HR AFTER INGESTION OF POISONOUS MUSHROOMS.|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.|ALPHA-AMANITIN WAS DETECTED IN THE BLOOD SERUM OF PATIENTS POISONED BY AMANITA PHALLOIDS BY USING REVERSED-PHASE, HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY WITH UV DETECTION. THE MINIMUM DETECTABLE AMOUNT OF ALPHA-AMANITIN WAS APPROX 10 NG (20 MUL OF 0.5 MUG/ML SOLUTION).

Computed Properties

Molecular Weight:919.0
XLogP3:-4.4
Hydrogen Bond Donor Count:13
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:7
Exact Mass:918.35416761
Monoisotopic Mass:918.35416761
Topological Polar Surface Area:400
Heavy Atom Count:64
Complexity:1840
Undefined Atom Stereocenter Count:11
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of ALPHA-AMANITIN

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.