Muscimol
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 Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...
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

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 GABA_A receptor. Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naptha or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... A psychoactive drug or psychotropic substance is a chemical that alters brain function, resulting in temporary changes in perception, mood, consciousness, or behaviour. ... Species 600, see List of Amanita species Synonyms Aspidella The genus Amanita contains about 600 species of agarics including some of the most toxic known mushrooms found worldwide. ... Psilocybin (also known as psilocybine) is a psychedelic alkaloid of the tryptamine family, found in psilocybin mushrooms. ... Tryptamine (3-(2-aminoethyl)indole) is a monoamine compound that is widespread in nature. ... Agonists An agonist is a substance that binds to a receptor and triggers a response in the cell. ... The GABAA receptor is one of the three ligand-gated ion channels responsible for mediating the effects of Gamma-AminoButyric Acid (GABA), the major inhibitory neurotransmitter in the brain. ...

Chemistry

Muscimol is the product of the decarboxylation or drying of ibotenic acid. A Decarboxylation is any chemical reaction in which a carboxyl group (-COOH) is split off from a compound as carbon dioxide (CO2). ... Categories: Stub | Amino acids ...

Biology

Amanita muscaria, which contains muscimol

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.[2],[3] It is thought that, 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. Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... Binomial name (L.:Fr. ... Binomial name (L.:Fr. ... Binomial name Amanita pantherina Amanita pantherina is a North American fungus. ... The Amanita Gemmata is a mushroom of the Amanita genus, a genus of fungi inclusive of some of the most deadly mushrooms, as well as notably psychedelic mushrooms. ... Muscarine, L-(+)-muscarine, or muscarin is a natural product found in certain mushrooms, particularly in Inocybe and Clitocybe species, such as the deadly C. dealbata. ... Categories: Stub | Amino acids ... Categories: Stub | Amino acids ... Binomial name (L.:Fr. ... A psychoactive drug or psychotropic substance is a chemical that alters brain function, resulting in temporary changes in perception, mood, consciousness, or behaviour. ...

Pharmacology

Muscimol is a potent GABA_A 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. When muscimol is administered, it has been shown active in the cerebral cortex, hippocampus, and cerebellum. The GABAA receptor is one of the three ligand-gated ion channels responsible for mediating the effects of Gamma-AminoButyric Acid (GABA), the major inhibitory neurotransmitter in the brain. ... Agonists An agonist is a substance that binds to a receptor and triggers a response in the cell. ... In biochemistry, a receptor is a protein on the cell membrane or within the cytoplasm or cell nucleus that binds to a specific molecule (a ligand), such as a neurotransmitter, hormone, or other substance, and initiates the cellular response to the ligand. ... Chemical structure of D-aspartic acid, a common amino acid neurotransmitter. ... Gaba may refer to: Gabâ or gabaa (Philippines), the concept of negative karma of the Cebuano people GABA, the gamma-amino-butyric acid neurotransmitter GABA receptor, in biology, receptors with GABA as their endogenous ligand Gaba 1 to 1, an English conversational school in Japan Marianne Gaba, a US model...

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. “EEG” redirects here. ... Indole is an aromatic heterocyclic organic compound. ...

When used in vivo, muscimol will pass through the human body, and be excreted (as muscimol) in the subject's urine. In vivo (Latin for (with)in the living). ...

The psychoactive dose of muscimol is around 15-20mg for a normal person^{[citation needed]}. A psychoactive drug or psychotropic substance is a chemical that alters brain function, resulting in temporary changes in perception, mood, consciousness, or behaviour. ...

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]

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. Psilocybin (also known as psilocybine) is a psychedelic alkaloid of the tryptamine family, found in psilocybin mushrooms. ... Lucid dreams occur during REM sleep after the person becomes conscious and aware of dreaming within the dream. ...

Synesthesia is also common, and increased sweating and salivation occurs from the action of another compound in the mushroom, muscarine. For other uses, see Synesthesia (disambiguation). ... For the band, see Saliva (band). ... Muscarine, L-(+)-muscarine, or muscarin is a natural product found in certain mushrooms, particularly in Inocybe and Clitocybe species, such as the deadly C. dealbata. ...

See also

• Psychedelic drug
• Psychoactive drug
• Amanita muscaria
• Ibotenic acid
• List of Entheogens

Psychedelic drugs are psychoactive drugs whose primary action is to alter the thought processes of the brain. ... An assortment of psychoactive drugs A psychoactive drug or psychotropic substance is a chemical substance that acts primarily upon the central nervous system where it alters brain function, resulting in temporary changes in perception, mood, consciousness and behavior. ... Binomial name (L.:Fr. ... Categories: Stub | Amino acids ... This is a partial list of Entheogenic substances: Entheogen Ethnobotany Categories: | ...

External links

• Psychoactive Amanitas on Erowid

References

1. ^ ^{a b} [1]

• 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:10.1016/0006-8993(78)90385-2. 
• S. R. Snodgrass (1978). "Use of ³H-muscimol for GABA receptor studies". Nature 273 (1): 392 - 394. doi:10.1038/273392a0. 
• 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:10.1016/0006-2952(68)90141-X.