H2O: 1 mg/mL 0.1 M NaOH: 10.7 mg/mL 0.1 M HCl: 4.7 mg/mL
Hazards
GHS labelling:[1]
Pictograms
Signal word
Danger
Hazard statements
H301
Precautionary statements
P264, P270, P301+P316, P321, P330, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Nverify (what is YN ?)
Infobox references
Chemical compound
Ibotenic acid or (S)-2-amino-2-(3-hydroxyisoxazol-5-yl)acetic acid, also referred to as ibotenate, is a chemical compound and psychoactive drug which occurs naturally in Amanita muscaria and related species of mushrooms typically found in the temperate and boreal regions of the northern hemisphere. It is a prodrug of muscimol, broken down by the liver to that much more stable compound.[2] It is a conformationally-restricted analogue of the neurotransmitter glutamate, and due to its structural similarity to this neurotransmitter, acts as a non-selective glutamate receptor agonist.[3] Because of this, ibotenic acid can be a powerful neurotoxin in high doses, and is employed as a "brain-lesioning agent" through cranial injections in scientific research.[4][5] The neurotoxic effects appear to be dose-related and risks are unclear through consumption of ibotenic-acid containing fungi, although thought to be negligible in small doses.[6][better source needed]
^"Ibotenic acid". pubchem.ncbi.nlm.nih.gov.
^Stebelska, Katarzyna (August 2013). "Fungal Hallucinogens Psilocin, Ibotenic Acid, and Muscimol: Analytical Methods and Biologic Activities". Therapeutic Drug Monitoring. 35 (4): 420–442. doi:10.1097/FTD.0b013e31828741a5. ISSN 0163-4356. PMID 23851905. S2CID 44494685.
^Tommy Liljefors; Povl Krogsgaard-Larsen; Ulf Madsen (25 July 2002). Textbook of Drug Design and Discovery, Third Edition. CRC Press. pp. 263–. ISBN 978-0-415-28288-8.
^Becker, A; Grecksch, G; Bernstein, HG; Höllt, V; Bogerts, B (1999). "Social behaviour in rats lesioned with ibotenic acid in the hippocampus: quantitative and qualitative analysis". Psychopharmacology. 144 (4): 333–8. doi:10.1007/s002130051015. PMID 10435405. S2CID 25172395.
^Isacson, O; Brundin, P; Kelly, PA; Gage, FH; Björklund, A (1984). "Functional neuronal replacement by grafted striatal neurones in the ibotenic acid-lesioned rat striatum". Nature. 311 (5985): 458–60. Bibcode:1984Natur.311..458I. doi:10.1038/311458a0. PMID 6482962. S2CID 4342937.
^Filer, Crist N. (1 December 2018). "Ibotenic acid: on the mechanism of its conversion to [3H] muscimol". Journal of Radioanalytical and Nuclear Chemistry. 318 (3): 2033–2038. doi:10.1007/s10967-018-6203-8. ISSN 1588-2780. S2CID 91380050.
Ibotenicacid or (S)-2-amino-2-(3-hydroxyisoxazol-5-yl)acetic acid, also referred to as ibotenate, is a chemical compound and psychoactive drug which occurs...
psychoactive constituents being muscimol and its neurotoxic precursor ibotenicacid. A local variety of the mushroom was used as an intoxicant and entheogen...
compounds responsible for the effects of Amanita muscaria intoxication. Ibotenicacid, a neurotoxic secondary metabolite of Amanita muscaria, serves as a...
concentration of ibotenicacid. While ibotenicacid is mostly broken down by the body into muscimol, what remains of the ibotenicacid is believed[according...
Glutamic acid (symbol Glu or E; the anionic form is known as glutamate) is an α-amino acid that is used by almost all living beings in the biosynthesis...
potential near 0 mV. AMPA was first synthesized, along with several other ibotenicacid derivatives, by Krogsgaard-Larsen, Honoré, and others toward differentiating...
di-(β-D-gentiobiosyl) ester; it bears the systematic (IUPAC) name 8,8-diapo-8,8-carotenoic acid. This means that the crocin underlying saffron's aroma is a digentiobiose...
catalyzes the hydrolysis of S-D-lactoylglutathione to glutathione and D-lactic acid. It maintains exogenous antioxidants such as vitamins C and E in their reduced...
formyle, an obsolete name for the methylidene radical (CH) derived from formic acid. The total global flux of chloroform through the environment is approximately...
/ˈɡlaɪsiːn/ ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid (carbamic acid is unstable). In the...
it is now known that the main effect of this mushroom is caused by ibotenicacid. Muscarine can also be found in some Inocybe species and Clitocybe species...
α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the...
aspartic acid is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. D-aspartic acid is one of two D-amino acids commonly...
an α-amino acid that is used in the biosynthesis of proteins. Its side chain is similar to that of glutamic acid, except the carboxylic acid group is replaced...
Glutamic acid (glutamate) – the endogenous agonist Ibotenicacid – a naturally occurring agonist found in Amanita muscaria Quisqualic acid – a naturally...
Hyoscyamine/hexamethylenetetramine/phenyl salicylate/methylene blue/benzoic acid (trade names Methylphen, Prosed DS) is a discontinued drug combination. It...
"Biological effects of the dihydroorotate dehydrogenase inhibitor polyporic acid, a toxic constituent of the mushroom Hapalopilus rutilans, in rats and humans"...
(February 1996). "Cloning of cDNAs encoding the human gamma-aminobutyric acid type A receptor alpha 6 subunit and characterization of the pharmacology...
is highly bound to plasma proteins (98.7%), mainly albumin, along with α1-acid glycoprotein (77%) and IgG (15%). Its metabolite N-desmethylatomoxetine is...
industrial scale by the acid ether synthesis. Ethanol is mixed with a strong acid, typically sulfuric acid, H2SO4. The acid dissociates in the aqueous...
variety)". www.erowid.org. "Erowid Psychoactive Amanitas Vault : Info on IbotenicAcid & Muscimol". www.erowid.org. Phillips, Roger (2010). Mushrooms and Other...
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