Psychoactive Amanitas Chemistry
by Erowid

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NAME :	Muscimol
CHEMICAL NAME :	5-(Aminomethyl)-3(2H)-isoxazolone
ALTERNATE CHEMICAL NAMES :	5-(aminomethyl)-3-isoxazolol, 5-aminomethyl-3-hydroxy-isaxazole
ALTERNATE CHEMICAL NAMES :	3-hydroxy-5-aminomethylisoxazole; agarin, pantherine
CHEMICAL FORMULA	C4H6N2O2
MOLECULAR WEIGHT	114.10
MELTING POINT	175° (crystals)
LD50	mice: 3.8 mg/kg s.c, 2.5 mg/kg i.p.
LD50	rats: 4.5 mg/kg i.v, 45 mg/kg orally
From the Merck Index 12th Edition

NAME :	Ibotenic Acid
CHEMICAL NAME :	alpha-Amino-2,3-dihydro-3-oxo-5-iso-xazoleacetic acid
ALTERNATE CHEMICAL NAMES :	alpha-amino-3-hydroxy-5-isoxazoleacetic acid
ALTERNATE CHEMICAL NAMES :	amino-(3-hydroxy-5-isoxazolyl)acetic acid
CHEMICAL FORMULA	C5H6N2O4
MOLECULAR WEIGHT	158.11
MELTING POINT	151-152° (anhydrous crystals)
MELTING POINT	144-146° (monohydrate crystals)
LD50	15 mg/kg i.v., 38 mg/kg oral (mice)
LD50	42 mg/kg i.v., 129 mg/kg oral (rats)
From the Merck Index 12th Edition

NAME :	Muscazone
CHEMICAL NAME :	alpha-Amino-2,3-dihydro-2-oxo-5-oxazoleacetic acid
ALTERNATE CHEMICAL NAMES :	alpha-amino-2-oxo-4-oxazoline-5-acetic acid
CHEMICAL FORMULA	C5H6N2O4
MOLECULAR WEIGHT	158.11
MELTING POINT
LD50
LD50
From the Merck Index 12th Edition

USE: As a molecular prove to study GABA receptors.

4922. Ibotenic Acid. alpha-Amino-2,3-dihydro-3-oxo-5-isoxazoleacetic acid; alpha-amino-3-hydroxy-5-isoxazoleacetic acid; amino-(3-hydroxy-5-isoxazolyl)acetic acid. C5H6N2O4; mol wt 158.11. C 37.98%, H 3.82%, N 17.72%, O 40.48%. Flykilling and narcosis-potentiating amino acid structurally similar to kainic acid, q.v., extracted from poisonous mushroom species. Isoln from Amanita pantherina (dc.) Fr., and A. muscaria (L.) Fr., Agaricaceae: Takemoto et al., J. Pharm. Soc. Japan 84, 1233 (1964); Eugster et al., Tetrahedron Letters 1965, 1813. Structure: Takemoto et al., J Pharm Soc. Japan 84, 1186, 1232 (1964). Syntheses: Gagneux et al., Tetrahedron Letters 1965, 2081; Sirakawa et al, Chem. Pharm. Bull. 14, 89 (1966); Kishida et al., ibid. 14, 92 (1966); 15, 1025 (1967). Improved synthesis: Nakamura, ibid. 19, 46 (1971). Industrial pats: Belg. pat 665,249, C.A. 65, 2266e (1966); Gagneux et al., U.S. pat. 3,459,862 (1965), 1969, both to Geigy); Kishida et al., Japan. pats 15,975-(68) 25,780(69) (both to Sankyo), C.A. 70, 77944p (1969); 72, 13054g (1970). Pharmaology: Theobald et al. Arzneimittel-Forsch. 18, 311 (1968); Johnston et al, Bio- chem. Pharmacol. 17, 2488 (1968). Exhibits potent neuroexcitatory activity: eidem. Nature 248, 804 (1974). Chemistry review: Eugster Fortschr. Chem. Org. Narurst. 27, 261-321 (1969); Catalfomo, Eugster, Bull. Narcotics 22, 33-41 (1970). Excitatory and possible sedative actions on spinal neurons: D.R. Curtis et at. J. Physiol. 291, 19 (1979); in cerebral cortex: E. Puil, Can. J. Physiol. Pharmacol. 59, 1025 (1981). Use as experimental neurotoxic agent: A. Contestabile et al Experientia 40, 524 (1984).

Crystals from water of methanol, mp 151-152© (anhydrous); mp 144-146© (monohydrate). LD50 in mice, rats (mg/kg): 15, 42 i.v.; 38, 129 orally (Theobald).

USE: Neurobiological tool.