Ibotenic Acid

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Other Names

a-amino (3-hydroxy-5-isoxazolyl)acetic acid, aamino-

2,3-dihydro-3-oxo-5-isoxazole-acetic acid,

ibotenic acid, «pilzatropin;' pramuscimol

Substance type: amino acid

Ibotenic acid was first isolated in 1964 from the

Japanese mushroom Amanita strobiliformis (Paul)

Quel. The Japanese name for this mushroom is ibotengu-

take ((warty tengu mushroom"), and

ibotenic acid was named after it (Ott 1993, 341*;

Takemoto et al. 1964). Ibotenic acid is also found

in Amanita muscaria and Amanita pantherina

(Eugster et al. 1965). It may also be present in

members of the genus Botelus (porcini mushrooms).

Ibotenic acid is structurally related to the

neurotransmitter glutamate and may behave

similarly in the nervous system. A psychoactive dose is regarded as 50 to 100 mg. Ibotenic acid is

converted into muscimol when stored (Good et al.

1965).
Commercial Forms and Regulations

Ibotenic acid is available from chemical suppliers

and is a legal substance (Ott 1993,440*).

Literature

See also the entries for Amanita muscaria,

Amanita pantherina, and muscimol.

Eugster, C. H., G. F. R. Muller, and R. Good. 1965.

Wirkstoffe aus Amanita muscaria: Ibotensaure

und Muscazon. Tetrahedron Letters 23:1813-15.

Gagneux, A. R., et al. 1965. Synthesis of ibotenic

acid. Tetrahedron Letters 965:2081-84.

Good, R., et al. 1965. Isolierung und

Charakterisierung von Pramuscimol und

Muscazon aus Amanita muscaria (1. ex Fr.)

Hooker. Helvetica Chimica Acta 48 (4): 927-30.

Romagnesi, M. H. 1964. Champignons toxiques au

Japon. Bulletin de la Societe Mycologique de

France 80 (1): iv-v.

Takemoto, T., T. Nakajima, and R. Sakuma. 1964.

Structure of ibotenic acid. Yakugaku Zasshi

84:1233.