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Trional

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Chemical compound

Pharmaceutical compound

Trional
Clinical data


ATC code	none
Legal status
Legal status	US: Schedule III
Identifiers
IUPAC name 2,2-bis(ethylsulfonyl)butane
CAS Number	76-20-0^N
PubChemCID	6433
ChemSpider	6193^Y
UNII	217727W28W
CompTox Dashboard(EPA)	DTXSID7046411
ECHA InfoCard	100.000.858
Chemical and physical data
Formula	C₈H₁₈O₄S₂
Molar mass	242.35 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCC(C)(S(=O)(=O)CC)S(=O)(=O)CC
InChI InChI=1S/C8H18O4S2/c1-5-8(4,13(9,10)6-2)14(11,12)7-3/h5-7H2,1-4H3^Y Key:LKACJLUUJRMGFK-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Trional (Methylsulfonal) is asedative-hypnotic^[1] andanesthetic drug withGABAergic actions^{[citation needed]}. It has similar effects tosulfonal, except it is faster acting.^[2]

History

[edit]

Trional was prepared and introduced byEugen Baumann andAlfred Kast in 1888.^[3]

Cultural references

[edit]

Appeared in Agatha Christie'sMurder on the Orient Express,And Then There Were None, and other novels such as John Bude'sThe Lake District Murder as a sleep-inducing sedative; and inIn Search of Lost Time (Sodom and Gomorrah) byMarcel Proust as ahypnotic.Sax Rohmer also references trional in his novelDope.

References

[edit]

^"Trional".Merck's 1907 Index. New York: Merck & Co. 1907. p. 448.
^Sajous CE (1896)."General Therapeutics".Annual of the Universal Medical Sciences.5. Philadelphia: F. A. Davis: A-156.
^Drinkwater H (1924).Fifty years of medical progress, 1873-1922. New York: The Macmillan Company. p. 40.

Hypnotics/sedatives (N05C)

GABA_A

Alcohols	2M2B Chloralodol Ethanol (alcohol) Diethylpropanediol Ethchlorvynol Methylpentynol Trichloroethanol
Barbiturates	Allobarbital Amobarbital Aprobarbital Barbital Butabarbital Butobarbital Cyclobarbital Ethallobarbital Heptabarb Hexobarbital Mephobarbital Methohexital Narcobarbital Pentobarbital Phenallymal Phenobarbital Propylbarbital Proxibarbal Reposal Secobarbital Talbutal Thiamylal Thiopental Thiotetrabarbital Vinbarbital Vinylbital
Benzodiazepines	Brotizolam Cinolazepam Climazolam Clonazolam Doxefazepam Estazolam Flubromazolam Flunitrazolam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Loprazolam Lormetazepam Midazolam Nimetazepam Nitemazepam Nitrazepam Nitrazolam Quazepam Temazepam Triazolam
Carbamates	Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate
Imidazoles	Etomidate Metomidate Propoxate
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Capuride Carbromal Ectylurea
Neurosteroids	Acebrochol Alfadolone Alfaxolone Brexanolone (allopregnanolone) Eltanolone (pregnanolone) Ganaxolone Hydroxydione Minaxolone Progesterone Renanolone Zuranolone
Nonbenzodiazepines	Eszopiclone Indiplon Lirequinil Necopidem Pagoclone Pazinaclone Saripidem Suproclone Suriclone Zaleplon Zolpidem Zopiclone
Phenols	Cipepofol (ciprofol) Fospropofol Propofol Propofol hemisuccinate
Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Others	Acetophenone Acetylglycinamide chloral hydrate Bromide compounds Lithium bromide Potassium bromide Sodium bromide Centalun Chloral betaine Chloral hydrate Chloralose Clomethiazole Dichloralphenazone Gaboxadol (THIP) Ibotenic acid (Amanita muscaria) Kavalactones Loreclezole Muscimol (Amanita muscaria) Paraldehyde Petrichloral Sesquiterpene Isovaleramide Isovaleric acid Valerenic acid Sulfonylalkanes Sulfonmethane (sulfonal) Tetronal Trional Triclofos

GABA_B

H₁

Antihistamines	Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Perlapine Pheniramine Promethazine Propiomazine
Antidepressants	Serotonin antagonists and reuptake inhibitors Etoperidone Nefazodone Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

α₂-Adrenergic

5-HT_2A

Antidepressants	Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.
Others	Niaprazine

Melatonin

Orexin

α₂δ VDCC

Others

Cannabinoids (e.g.,cannabis,tetrahydrocannabinol/dronabinol,nabilone,cannabidiol,Zenivol)
Chlorophenylalkyldiols
Diethylpropanediol
Evoxine
Fenadiazole
GABA reuptake inhibitors (e.g.,tiagabine)
Guaifenesin-relatedmuscle relaxants
Midaflur
Opioids (e.g.,morphine)
Passion flower
Phemerazole
Scopolamine
Serotonin precursors (e.g.,tryptophan,5-hydroxytryptophan (5-HTP;oxitriptan))
Trazodone
UMB68
Valnoctamide

General anesthetics (N01A)

Inhalational

Injection

Phenols	Cipepofol (ciprofol)^† Fospropofol Propofol^#
Barbiturates	Amobarbital Hexobarbital Methohexital Narcobarbital Thiamylal Thiopental^# Thiotetrabarbital
Benzodiazepines	Midazolam^# Diazepam^# Lorazepam^# Remimazolam
Opioids	Morphine^# Oxycodone Anileridine^‡ Embutramide^‡ Fentanyl^# Alfentanil Phenoperidine Remifentanil÷ Sufentanil
Arylcyclohexylamines	Esketamine Ketamine^# Phencyclidine^‡ Tiletamine
Neuroactive steroids	Alfadolone Alfaxalone Hydroxydione
Others	Etomidate Propoxate Metomidate Propanidid^‡

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

v t e GABA_A receptor positive modulators
Alcohols	Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol
Barbiturates	(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital
Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Bromazolam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Dimdazenil Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam
Carbamates	Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Hydroxyphenamate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate
Flavonoids	6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g.,baicalin) Wogonin
Imidazoles	Etomidate Metomidate Methoxyetomidate Propoxate Isopropoxate Butomidate Iso-butomidate Sec-butomidate CF2-Etomidate CF3-Etomidate CF3-Propoxate Flutomidate 2,6-Dichloro-3-fluoroetomidate
Kava constituents	10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea
Neuroactive steroids	Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certainanabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Posovolone Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC Zuranolone
Nonbenzodiazepines	Cyclopyrrolones:Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines:Alpidem DS-1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines:Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others:Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil (Ro41-3696) Miltirone (rosmariquinone) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684
Phenols	Cipepofol Fospropofol Propofol Propofol hemisuccinate Thymol
Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione
Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Volatiles/gases	Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether
Others/unsorted	3-Hydroxybutanal α-EMTBL AA-29504 Alogabat Avermectins (e.g.,ivermectin) Bromide compounds (e.g.,lithium bromide,potassium bromide,sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole Darigabat DEABL Deuterated etifoxine Dihydroergolines (e.g.,dihydroergocryptine,dihydroergosine,dihydroergotamine,ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g.,flufenamic acid,mefenamic acid,niflumic acid,tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid KRM-II-81 Lanthanum Lavender oil Lignans (e.g.,4-O-methylhonokiol,honokiol,magnolol,obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Nicotinic acid Nicotinamide Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g.,sulfonmethane (sulfonal),tetronal,trional) Terpenoids (e.g.,borneol) Topiramate Valerian constituents (e.g.,isovaleric acid,isovaleramide,valerenic acid,valerenol) Unsorted benzodiazepine site positive modulators:α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205
See also:Receptor/signaling modulators •GABA receptor modulators •GABA metabolism/transport modulators

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