Acido ibotenico

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Acido ibotenico
formula di struttura
formula di struttura
Modello ad asta e sfera
Modello ad asta e sfera
Nome IUPAC
acido α-ammino-2,3-diidro-3-osso-5-isossazolacetico
Nomi alternativi
acido alfa-ammino-3-idrossi-5-isossazoloacetico
Caratteristiche generali
Formula bruta o molecolareC5H6N2O4
Massa molecolare (u)158,11
Numero CAS2552-55-8
Numero EINECS622-405-7
PubChem1233 e 12310764
SMILES
C1=C(ONC1=O)C(C(=O)O)N
Proprietà chimico-fisiche
Temperatura di fusione151 °C (anidro), 144 °C (monoidrato)
Proprietà tossicologiche
DL50 (mg/kg)15 mg/kg somministrazione endovenosa nel topo, 38 mg/kg somministrazione orale nel topo
Indicazioni di sicurezza
Simboli di rischio chimico
tossicità acuta
pericolo
Frasi H301
Consigli P301+310 [1]
Modifica dati su Wikidata · Manuale

L'acido ibotenico è una tossina presente nell'Amanita muscaria e nell'Amanita pantherina.

In particolare è stato osservato che l'acido ibotenico, strutturalmente correlato all'acido glutammico, causa eccitazione, a differenza del muscimolo essendo più simile all'acido γ-amminobutirrico, esercita un effetto depressivo. L'effetto allucinogeno del muscimolo è circa cinque volte superiore rispetto a quello dell'acido ibotenico,[2]

Meccanismo d'azione e quadro clinico

L'acido ibotenico è un agonista del recettore glutammato, Nel ratto la somministrazione intraperitoneale di un estratto acquoso di Amanita muscaria (contenente acido ibotenico), induce alterazioni a carico di alcuni parametri ematochimici. In particolare, si osserva ridotta attività dell'acetilcolinesterasi, riduzione dei livelli epatici di glicogeno con conseguente incremento della glicemia e riduzione dell'azotemia. Non viene invece modificata l'attività delle transaminasi seriche e non sono compromessi organi vitali quali fegato e reni. Nel giro di sei ore i valori modificati dall'ingestione del fungo tendono a normalizzarsi[3].

L'intossicazione da acido ibotenico si manifesta con scoppi d'ira e di ilarità, e allucinazioni alle quali segue uno stato di torpore e spossatezza.

Legislazione

In Italia né l'acido ibotenico, né il muscimolo e il muscazone sono inseriti nelle Tabelle contenenti le sostanze stupefacenti o psicotrope sottoposte alla vigilanza e al controllo di cui all'articolo 14 del Decreto del Presidente della Repubblica n. 309/1990 e successive modifiche. In molti paesi europei (Svezia, Norvegia, Paesi Bassi, Finlandia, Danimarca, Regno Unito) i funghi che contengono queste molecole possono essere legalmente comprati, venduti e posseduti. In Canada i funghi non risultano sottoposti a controllo. Negli Stati Uniti, in particolare nello Stato della Louisiana, l'utilizzo non è legale se riferito all'uomo, mentre la legge permette il possesso per scopi rigorosamente estetici, paesaggistici e decorativi.

Note

  1. ^ Sigma Aldrich; rev. del 13.03.2010
  2. ^ 9. WALKER RJ, WOODRUFF GN, KERKUT GA. The effect of ibotenic acid and muscimol on single neurons of the snail, Helix aspersa. Comp Gen Pharmacol. 1971; 2: 168-174.
  3. ^ 11. YAMAHURA Y, KOMIYMA S, FUKUHARA M, TAKABATAKE E, HASIMOTA T. Biochemical effects of Amanita muscaria extract in mice. Journal of Food and Hygiene Society of Japan (Shokuhin Eiseigaku Zasshi) 1983; 24: 459-464.

Voci correlate

Altri progetti

Controllo di autoritàGND (DE) 4239824-1
  Portale Biologia

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