Muscimol
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| Muscimol | |
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| IUPAC name | 5-(Aminomethyl)-3(2H)-isoxazolone |
| Molecular formula | C4H6N2O2 |
| Identifiers | |
| CAS number | [18174-72-6] |
| SMILES | NCc1cc(O)no1 |
| Properties | |
| Molar mass | 114.10 g/mol |
| Melting point |
184-185°C |
| Solubility in water | very soluble |
| Solubility in ethanol | slightly soluble |
| Solubility in methanol | very soluble |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Muscimol (Agarin, Pantherine) is the major psychoactive alkaloid present in many mushrooms of the Amanita genus. Unlike psilocybin, a tryptamine, muscimol is a potent, selective agonist of the GABAA receptor.
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[edit] Chemistry
Muscimol is the product of the decarboxylation or drying of ibotenic acid.
[edit] Biology
Muscimol is produced naturally in the mushrooms Amanita muscaria, Amanita pantherina, and Amanita gemmata, along with muscarine, muscazone, and ibotenic acid. Of these, only A. muscaria and A. pantherina are considered somewhat safe for human consumption, with the other being far more dangerous; however lethal poisonings have occurred from A. muscaria and A. pantherina as well.[1],[2] It is thought that[who?], in A. muscaria, the layer just below the skin of the cap contains the highest amount of muscimol, and is therefore the most psychoactive portion.
[edit] Pharmacology
Muscimol is a potent GABAA agonist, which is a receptor for the brain's major inhibitory neurotransmitter, GABA. The primary use for muscimol has become lab research, as the chemical essentially "turns off" part of the brain.[citation needed] When muscimol is administered, it has been shown active in the cerebral cortex, hippocampus, and cerebellum.
During a test involving rabbits connected to an EEG, muscimol showed a distinctly synchronized EEG tracing. This is substantially different from indolic psychedelics, as brainwave patterns will generally show a desynchronization. In higher doses (2mg/kg), the EEG will show characteristic spikes.
When used in vivo, muscimol will pass through the human body, and be excreted (as muscimol) in the subject's urine.
The psychoactive dose of muscimol is around 15-20mg for a normal person[citation needed].
[edit] Toxicity
LD50 mice: 3.8 mg/kg s.c, 2.5 mg/kg i.p.[1]
LD50 rats: 4.5 mg/kg i.v, 45 mg/kg orally.[1]
[edit] Effects
The effects of muscimol are substantially different from psilocybin, as the chemicals target separate parts of the brain. Muscimol has been shown to lack "structured" hallucinations in most cases, and the effects are frequently compared to a lucid dream state.
[edit] See also
[edit] External links
[edit] References
- Merck Index, 12th Edition
- Ito Y, Segawa K, Fukuda H. 1995 "Functional diversity of GABAA receptor ligand-gated chloride channels in rat synaptoneurosomes" Synapse 19(3):188-96.
- Rätsch, Christian. (1998). The Encyclopedia of Psychoactive Plants. Rochester, VT: Park Street Press.
- Beaumont K, Chilton W. S., Yamamura H. I., Enna S. J. (1978). "Muscimol binding in rat brain: association with synaptic GABA receptors.". Brain Res. 148 (1): 153-62. doi:.
- S. R. Snodgrass (1978). "Use of 3H-muscimol for GABA receptor studies". Nature 273 (1): 392 - 394. doi:.
- G. A. R. Johnston, D. R. Curtis, W. C. de Groat and A. W. Duggan (1968). "Central actions of ibotenic acid and muscimol". Biochemical Pharmacology 17 (12): 2488-2489. doi:.
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