From Wikipedia, the free encyclopedia
Thiomuscimol
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Names
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Preferred IUPAC name
5-(Aminomethyl)-1,2-thiazol-3-ol
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Identifiers
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ChemSpider
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InChI=1S/C4H6N2OS/c5-2-3-1-4(7)6-8-3/h1H,2,5H2,(H,6,7) Key: QVBUOPGWPXUAHT-UHFFFAOYSA-N
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Properties
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C4H6N2OS
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Molar mass
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130.17 g·mol−1
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Melting point
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140 °C (decomp.)[1]
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Acidity (pKa)
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6.06 ± 0.03, 8.85 ± 0.04 (H2O, 21 °C)
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Thiomuscimol is a GABAA receptor agonist which is structurally related to muscimol.[2]
- ^ Lykkeberg, Jytte; Krogsgaard-Larsen, Povl; Garegg, Per J.; Norberg, Thomas; Pilotti, Anne-Marie; Anthonsen, T. (1976). "Structural Analogues of GABA. Synthesis of 5-Aminomethyl-3-isothiazolol (Thiomuscimol)". Acta Chemica Scandinavica. 30b: 781–785. doi:10.3891/acta.chem.scand.30b-0781.
- ^ Krogsgaard-Larsen, P; Hjeds, H; Curtis, DR; Lodge, D; Johnston, GA (1979). "Dihydromuscimol, thiomuscimol and related heterocyclic compounds as GABA analogues". Journal of Neurochemistry. 32 (6): 1717–24. doi:10.1111/j.1471-4159.1979.tb02284.x. PMID 448364. S2CID 1393563.
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Ionotropic | GABAATooltip γ-Aminobutyric acid A receptor |
- Positive modulators (abridged; see here for a full list): α-EMTBL
- Alcohols (e.g., drinking alcohol, 2M2B)
- Anabolic steroids
- Avermectins (e.g., ivermectin)
- Barbiturates (e.g., phenobarbital)
- Benzodiazepines (e.g., diazepam)
- Bromide compounds (e.g., potassium bromide)
- Carbamates (e.g., meprobamate)
- Carbamazepine
- Chloralose
- Chlormezanone
- Clomethiazole
- Dihydroergolines (e.g., ergoloid (dihydroergotoxine))
- Etazepine
- Etifoxine
- Fenamates (e.g., mefenamic acid)
- Flavonoids (e.g., apigenin, hispidulin)
- Fluoxetine
- Flupirtine
- Imidazoles (e.g., etomidate)
- Kava constituents (e.g., kavain)
- Lanthanum
- Loreclezole
- Monastrol
- Neuroactive steroids (e.g., allopregnanolone, cholesterol, THDOC)
- Niacin
- Niacinamide
- Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil), cyclopyrrolones (e.g., zopiclone), imidazopyridines (e.g., zolpidem), pyrazolopyrimidines (e.g., zaleplon))
- Norfluoxetine
- Petrichloral
- Phenols (e.g., propofol)
- Phenytoin
- Piperidinediones (e.g., glutethimide)
- Propanidid
- Pyrazolopyridines (e.g., etazolate)
- Quinazolinones (e.g., methaqualone)
- Retigabine (ezogabine)
- ROD-188
- Skullcap constituents (e.g., baicalin)
- Stiripentol
- Sulfonylalkanes (e.g., sulfonmethane (sulfonal))
- Topiramate
- Valerian constituents (e.g., valerenic acid)
- Volatiles/gases (e.g., chloral hydrate, chloroform, diethyl ether, paraldehyde, sevoflurane)
- Negative modulators: 1,3M1B
- 3M2B
- 11-Ketoprogesterone
- 17-Phenylandrostenol
- α3IA
- α5IA (LS-193,268)
- β-CCB
- β-CCE
- β-CCM
- β-CCP
- β-EMGBL
- Anabolic steroids
- Amiloride
- Anisatin
- β-Lactams (e.g., penicillins, cephalosporins, carbapenems)
- Basmisanil
- Bemegride
- Bicyclic phosphates (TBPS, TBPO, IPTBO)
- BIDN
- Bilobalide
- Bupropion
- CHEB
- Chlorophenylsilatrane
- Cicutoxin
- Cloflubicyne
- Cyclothiazide
- DHEA
- DHEA-S
- Dieldrin
- (+)-DMBB
- DMCM
- DMPC
- EBOB
- Etbicyphat
- FG-7142 (ZK-31906)
- Fiproles (e.g., fipronil)
- Flavonoids (e.g., amentoflavone, oroxylin A)
- Flumazenil
- Fluoroquinolones (e.g., ciprofloxacin)
- Flurothyl
- Furosemide
- Golexanolone
- Iomazenil (123I)
- IPTBO
- Isopregnanolone (sepranolone)
- L-655,708
- Laudanosine
- Lindane
- MaxiPost
- Morphine
- Morphine-3-glucuronide
- MRK-016
- Naloxone
- Naltrexone
- Nicardipine
- Nonsteroidal antiandrogens (e.g., apalutamide, bicalutamide, enzalutamide, flutamide, nilutamide)
- Oenanthotoxin
- Pentylenetetrazol (pentetrazol)
- Phenylsilatrane
- Picrotoxin (i.e., picrotin, picrotoxinin and dihydropicrotoxinin)
- Pregnenolone sulfate
- Propybicyphat
- PWZ-029
- Radequinil
- Ro 15-4513
- Ro 19-4603
- RO4882224
- RO4938581
- Sarmazenil
- SCS
- Suritozole
- TB-21007
- TBOB
- TBPS
- TCS-1105
- Terbequinil
- TETS
- Thujone
- U-93631
- Zinc
- ZK-93426
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GABAA-ρTooltip γ-Aminobutyric acid A-rho receptor | |
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Metabotropic | GABABTooltip γ-Aminobutyric acid B receptor | |
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