Ibotenic acid

Structural formula
General
Surname	Ibotenic acid
other names	( S ) -2-Amino-2- (3-hydroxyisoxazol-5-yl) acetic acid
Molecular formula	C 5 H 6 N 2 O 4
Brief description	colorless crystals
External identifiers / databases
CAS number 2552-55-8 EC number 622-405-7 ECHA InfoCard 100.151.170 PubChem 1233 ChemSpider 1196 Wikidata Q411094
properties
Molar mass	158.11 g mol −1
Physical state	firmly
Melting point	151-152 ° C
solubility	bad in water, good in ethanol
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 301 P: 301 + 310
Toxicological data	38 mg kg −1 ( LD 50 ,  mouse ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ibotenic acid , also known as premuscimol , is a psychoactive , non-proteinogenic L- amino acid (racemized during isolation) that occurs in various mushrooms of the amulas genus , for example in the toadstool and panther mushroom .

Biological importance

The orange pigment of the fly agaric ( Amanita muscaria L.) is an iminium salt of ibotenic acid and betalamic acid .

Ibotenic acid is the metabolic precursor of muscimol . An ibotenic acid-betalamic acid conjugate (musca-aurin I), a betaxanthin , was identified as a component of the coloring components of the toadstool dyes .

The biosynthesis of ibotenic acid most likely begins with the hydroxylation of glutamate using an iron / 2-ketoglutarate-dependent oxygenase. The threo -3-hydroxyglutamate formed is then converted into ibotenic acid in several enzymatic steps.

effect

Ibotenic acid is a fungal toxin with a central nervous effect. Initially, it leads to symptoms similar to alcohol intoxication with unsteady gait, later to motor paralysis, but also to hyperkinesis , muscle cramps and delirium .

Ibotenic acid binds to glutamate receptors on the tongue and triggers an umami taste.

During cooking and drying, ibotenic acid is converted into muscimol through decarboxylation , the hallucinogenic effect of which is significantly stronger.

Individual evidence

1. ↑ ^{a b c} Entry on ibotenic acid. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.
2. ↑ ^{a b} Datasheet Ibotenic acid from Sigma-Aldrich , accessed on April 4, 2011 ( PDF ).
3. ↑ Entry on ibotenic acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .
4. ↑ Oliver Sauer: Drugs. Schlütersche, 2001, ISBN 978-3-877-06601-0 , p. 67.
5. ^ ^{A b} Franz-Xaver Reichl: Pocket Atlas of Toxicology. Georg Thieme Verlag, 2002, ISBN 978-3-131-08972-4 , p. 272.
6. ↑ Norio Nakamura: The Improved Syntheses of dl-Ibotenic Acid and Muscimol . In: CHEMICAL & PHARMACEUTICAL BULLETIN . tape 19 , no. 1 , 1971, ISSN  0009-2363 , pp. 46–51 , doi : 10.1248 / cpb.19.46 ( jst.go.jp [accessed April 11, 2020]).
7. ^ Albert Gossauer: Structure and Reactivity of Biomolecules , Verlag Helvetica Chimica Acta, Zurich, 2006, p. 483, ISBN 978-3-906390-29-1 .
8. ↑ Sebastian Obermaier, Michael Müller: Ibotenic Acid Biosynthesis in the Fly Agaric Is Initiated by Glutamate Hydroxylation . In: Angewandte Chemie International Edition . March 31, 2020, doi : 10.1002 / anie.202001870 ( wiley.com [accessed April 11, 2020]).
9. ↑ Ernst Steinegger: Textbook of Pharmacognosy and Phytopharmacy. Springer-Verlag, 2013, ISBN 978-3-662-08318-5 , p. 446.
10. ↑ Hans-Dieter Belitz , Werner Grosch : Textbook of food chemistry. Springer-Verlag, 2007, ISBN 978-3-540-73202-0 , p. 442.
11. ↑ HN Lioe, J. Selamat, M. Yasuda: Soy sauce and its umami taste: a link from the past to current situation. In: Journal of food science. Volume 75, number 3, April 2010, pp. R71-R76, doi : 10.1111 / j.1750-3841.2010.01529.x , PMID 20492309 .
12. ^ Franz von Bruchhausen: Hager's Handbook of Pharmaceutical Practice. Springer-Verlag, 1938, ISBN 978-3-540-52688-9 , p. 67.

Web links

Wiktionary: Ibotenic acid  - explanations of meanings, word origins, synonyms, translations