Erowid
 
 
Plants - Drugs Mind - Spirit Freedom - Law Arts - Culture Library  
It's Erowid's 20th Anniversary!
Help us keep going for another twenty with a small donation?
Erowid is a global information resource. We're an educational non-profit working to provide an honest look at psychoactives. Accurate info is required in order to move forward with research, drug law reform, and safer use. This work is made possible by small donations and memberships (get our newsletter!).
Psychoactive Amanitas Chemistry
by Erowid

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 FORMULAC4H6N2O2
MOLECULAR WEIGHT114.10
MELTING POINT175° (crystals)
LD50mice: 3.8 mg/kg s.c, 2.5 mg/kg i.p.
LD50rats: 4.5 mg/kg i.v, 45 mg/kg orally
From the Merck Index 12th Edition


Muscimol Molecule


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 FORMULAC5H6N2O4
MOLECULAR WEIGHT158.11
MELTING POINT151-152° (anhydrous crystals)
MELTING POINT144-146° (monohydrate crystals)
LD5015 mg/kg i.v., 38 mg/kg oral (mice)
LD5042 mg/kg i.v., 129 mg/kg oral (rats)
From the Merck Index 12th Edition


Ibotenic Acid Molecule

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 FORMULAC5H6N2O4
MOLECULAR WEIGHT158.11
MELTING POINT 
LD50 
LD50 
From the Merck Index 12th Edition


Muscazone Acid Molecule




MERCK INDEX ENTRY
6391. Muscimol. 5-(Aminomethyl)-3(2H)-isoxazolone; 5-(aminomethyl)-3-isoxazolol; 5-aminomethyl-3-hydroxy-isaxazole; 3-hydroxy-5-aminomethylisoxazole; agarin, pantherine. C4H6N2O2; mol wt 114.10. C 42.11%, H 5.30%, N 24.55%, O 28.04%. Potent CNS depressant and GABA agonist isolated from Amanita muscaria (L.) Fr., Agaricaceae. Structural identity with the insecticidal substances, pantherine and agarin: Onda et al., Chem Pharm. Bull. 12, 751 (1964); Eugster et al., Tetrahedron Letters 1965, 1813; Bowden, Drysdale, ibid. 727. Synthesis: Gagneux et al., ibid. 2077; Goth et al., Helv. Chim. Acta 50, 137 (1967); Bowden et al., J. Chem. Soc. (C) 1968, 172. Improved syntheses: Nakamura, Chem. Pharm. Bull. 19, 46 (1971); P. Krogsgaard-Larsen, S.B. Christensen, Acta Chem. Scand. Ser. B B30, 281 (1976); A. Barco et al., J. Chem. Res. (S) 1979, 176; B. E. McCarry, M. Savard, Tetrahedron Letters 22, 5153 (1981); V. Jager, M. Frey, Ann. 1982, 817. Conformational structure: L. Brehm et al., ibid. 26, 1298 (1972). Industrial patents: Hafliger, Gagneux, U.S. pats. 3,242,190, 3,397,209 (1966, 1968 both to Geigy). Pharmacology: Theobald et al., Arzneimittel-Forsch. 18, 311 (1968). Review of pharmacology: F. V. DeFeudis, Neurochem. Res. 5, 1047-1068 (1980).

Muscimol Molecule

Crystals, mp 175° (dec). LD50 in mice (mg/kg): 3.8 s.c., 2.5 i.p.; in rats (mg/kg): 4.5 i.v., 45 orally (Theobald).

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.