Muscimol hydrobromide
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Basic Info
| Common Name | Muscimol hydrobromide(F04687) |
| 2D Structure | |
| Description | 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. Amanita muscaria contains two main active ingredients, Ibotenic acid and its derivative Muscimol. Muscimol is the product of the decarboxylation or drying of ibotenic acid and it is thought that muscimol is as much as ten times more potent than ibotenic acid. (L1142) |
| FRCD ID | F04687 |
| CAS Number | 18174-72-6 |
| PubChem CID | 205536 |
| Formula | C4H7BrN2O2 |
| IUPAC Name | 5-(aminomethyl)-1,2-oxazol-3-one;hydrobromide |
| InChI Key | OPZOJWHOZRKYQX-UHFFFAOYSA-N |
| InChI | InChI=1S/C4H6N2O2.BrH/c5-2-3-1-4(7)6-8-3;/h1H,2,5H2,(H,6,7);1H |
| Canonical SMILES | C1=C(ONC1=O)CN.Br |
| Isomeric SMILES | C1=C(ONC1=O)CN.Br |
| Wikipedia | Muscimol hydrobromide |
| Synonyms |
5-(Aminomethyl)-3(2H)-isoxazolone hydrobromide
Muscimol hydrobromide
18174-72-6
Agarin hydrobromide
5-Aminomethyl-3-hydroxyisoxazole hydrobromide
3(2H)-Isoxazolone, 5-(aminomethyl)-, monohydrobromide
5-(Aminomethyl)-3-isoxazolol monohydrobromide
5-Aminomethyl-3-isoxyzole hydrobromide
5-(Aminomethyl)-3-isoxazolol hydrobromide
3-Hydroxy-5-aminomethylisoxazole hydrobromide
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic nitrogen compounds |
| Class | Organonitrogen compounds |
| Subclass | Amines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Aralkylamines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Aralkylamine - Azole - Isoxazole - Heteroaromatic compound - Lactam - Oxacycle - Azacycle - Organoheterocyclic compound - Hydrobromide - Organic oxygen compound - Primary amine - Organooxygen compound - Primary aliphatic amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 195.016 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 141 |
| Monoisotopic Mass | 193.969 |
| Exact Mass | 193.969 |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 2 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9908 |
| Human Intestinal Absorption | HIA+ | 0.9972 |
| Caco-2 Permeability | Caco2- | 0.6452 |
| P-glycoprotein Substrate | Non-substrate | 0.8469 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8934 |
| Non-inhibitor | 0.9172 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8693 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4389 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.9078 |
| CYP450 2D6 Substrate | Non-substrate | 0.8056 |
| CYP450 3A4 Substrate | Non-substrate | 0.5822 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8205 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8611 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8915 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8305 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8242 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5695 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9894 |
| Non-inhibitor | 0.8108 | |
| AMES Toxicity | AMES toxic | 0.5712 |
| Carcinogens | Non-carcinogens | 0.8333 |
| Fish Toxicity | Low FHMT | 0.9809 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8351 |
| Honey Bee Toxicity | Low HBT | 0.7213 |
| Biodegradation | Not ready biodegradable | 0.9746 |
| Acute Oral Toxicity | I | 0.6621 |
| Carcinogenicity (Three-class) | Non-required | 0.4081 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.6156 | LogS |
| Caco-2 Permeability | 0.5008 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.2583 | LD50, mol/kg |
| Fish Toxicity | 1.9298 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3403 | pIGC50, ug/L |
Targets
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA2
- Uniprot ID:
- P47869
- Molecular Weight:
- 51325.85 Da
- Mechanism of Action:
- Muscimol is a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets.
References
- Wikipedia. Muscimol. Last Updated 5 June 2009. : http://en.wikipedia.org/wiki/Muscimol
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA3
- Uniprot ID:
- P34903
- Molecular Weight:
- 55164.055 Da
- Mechanism of Action:
- Muscimol is a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets.
References
- Wikipedia. Muscimol. Last Updated 5 June 2009. : http://en.wikipedia.org/wiki/Muscimol
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA4
- Uniprot ID:
- P48169
- Molecular Weight:
- 61622.645 Da
- Mechanism of Action:
- Muscimol is a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets.
References
- Wikipedia. Muscimol. Last Updated 5 June 2009. : http://en.wikipedia.org/wiki/Muscimol
- General Function:
- Transporter activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA5
- Uniprot ID:
- P31644
- Molecular Weight:
- 52145.645 Da
- Mechanism of Action:
- Muscimol is a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets.
References
- Wikipedia. Muscimol. Last Updated 5 June 2009. : http://en.wikipedia.org/wiki/Muscimol
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA6
- Uniprot ID:
- Q16445
- Molecular Weight:
- 51023.69 Da
- Mechanism of Action:
- Muscimol is a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets.
References
- Wikipedia. Muscimol. Last Updated 5 June 2009. : http://en.wikipedia.org/wiki/Muscimol
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRG3
- Uniprot ID:
- Q99928
- Molecular Weight:
- 54288.16 Da
- Mechanism of Action:
- Muscimol is a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets.
References
- Wikipedia. Muscimol. Last Updated 5 June 2009. : http://en.wikipedia.org/wiki/Muscimol
- General Function:
- Gaba-a receptor activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-2 GABA receptor could play a role in retinal neurotransmission.
- Gene Name:
- GABRR2
- Uniprot ID:
- P28476
- Molecular Weight:
- 54150.41 Da
- Mechanism of Action:
- Muscimol is an agonist of the Gamma-aminobutyric acid receptor
References
- Tomaszewska-Zaremba D, Mateusiak K, Przekop F: The role of GABA(A) receptors in the neural systems of the medial preoptic area in the control of GnRH release in ewes during follicular phase. Anim Reprod Sci. 2003 May 15;77(1-2):71-83. [12654529 ]
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
- Gene Name:
- GABRA1
- Uniprot ID:
- P14867
- Molecular Weight:
- 51801.395 Da
- Mechanism of Action:
- Muscimol is a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets.
References
- Wikipedia. Muscimol. Last Updated 5 June 2009. : http://en.wikipedia.org/wiki/Muscimol
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRG1
- Uniprot ID:
- Q8N1C3
- Molecular Weight:
- 53594.49 Da
- Mechanism of Action:
- Muscimol is a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets.
References
- Wikipedia. Muscimol. Last Updated 5 June 2009. : http://en.wikipedia.org/wiki/Muscimol
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
- Gene Name:
- GABRG2
- Uniprot ID:
- P18507
- Molecular Weight:
- 54161.78 Da
- Mechanism of Action:
- Muscimol is a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets.
References
- Wikipedia. Muscimol. Last Updated 5 June 2009. : http://en.wikipedia.org/wiki/Muscimol
- General Function:
- G-protein coupled gaba receptor activity
- Specific Function:
- Component of a heterodimeric G-protein coupled receptor for GABA, formed by GABBR1 and GABBR2. Within the heterodimeric GABA receptor, only GABBR1 seems to bind agonists, while GABBR2 mediates coupling to G proteins. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase, stimulates phospholipase A2, activates potassium channels, inactivates voltage-dependent calcium-channels and modulates inositol phospholipid hydrolysis. Calcium is required for high affinity binding to GABA. Plays a critical role in the fine-tuning of inhibitory synaptic transmission. Pre-synaptic GABA receptor inhibits neurotransmitter release by down-regulating high-voltage activated calcium channels, whereas postsynaptic GABA receptor decreases neuronal excitability by activating a prominent inwardly rectifying potassium (Kir) conductance that underlies the late inhibitory postsynaptic potentials. Not only implicated in synaptic inhibition but also in hippocampal long-term potentiation, slow wave sleep, muscle relaxation and antinociception. Activated by (-)-baclofen, cgp27492 and blocked by phaclofen.Isoform 1E may regulate the formation of functional GABBR1/GABBR2 heterodimers by competing for GABBR2 binding. This could explain the observation that certain small molecule ligands exhibit differential affinity for central versus peripheral sites.
- Gene Name:
- GABBR1
- Uniprot ID:
- Q9UBS5
- Molecular Weight:
- 108319.4 Da
- Mechanism of Action:
- Muscimol is an agonist of the Gamma-aminobutyric acid receptor
References
- Belozertseva IV, Andreev BV: [A pharmaco-ethological study of the GABA-ergic mechanisms regulating the depression-like behavior of mice]. Zh Vyssh Nerv Deiat Im I P Pavlova. 1997 Nov-Dec;47(6):1024-31. [9472168 ]