Crotylbarbital

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Crotylbarbital

Systematic (IUPAC) name
5-but-2-enyl-5-ethyl-1,3-diazinane-2,4,6-trione
Clinical data
Legal status	?
Identifiers
CAS number	1952-67-6
ATC code	None
PubChem	CID 5364821
ChemSpider	4516954^Y
Chemical data
Formula	C₁₀H₁₄N₂O₃
Mol. mass	210.23 g/mol
SMILES O=C1NC(=O)NC(=O)C1(CC)C/C=C/C
InChI InChI=1S/C10H14N2O3/c1-3-5-6-10(4-2)7(13)11-9(15)12-8(10)14/h3,5H,4,6H2,1-2H3,(H2,11,12,13,14,15)/b5-3+^Y Key:KNMOHCLEINXVBG-HWKANZROSA-N^Y
Y (what is this?) (verify)

Crotylbarbital (Mepertan, Kalipnon, Barotal), also known as crotarbital, is a barbiturate derivative developed by Eli Lilly in the 1930s^[1]m It has sedative and hypnotic effects,^[2] and was used for the treatment of insomnia until it was replaced by newer alternative drugs with less side effects and lower risk of overdose.

References

↑ US Patent 2250422
↑ Walther T, Meyer FP, Puchta K, Walther H. Effect of an acute dose of crotylbarbital on reaction time and attention testing in healthy human subjects. International Journal of Clinical Pharmacology, Therapy and Toxicology. 1983 Jun;21(6):306-10.

Hypnotics/sedatives (N05C)

GABA_A
agonists/PAMs

Alcohols:	2M2B Chloralodol Ethanol Alcohol Ethchlorvynol Methylpentynol Trichloroethanol

Barbiturates:	Allobarbital Amobarbital Aprobarbital Barbital Butabarbital Butobarbital Cyclobarbital Ethallobarbital Heptabarb Hexobarbital Mephobarbital Methohexital Pentobarbital Phenallymal Phenobarbital Propylbarbital Proxibarbal Reposal Secobarbital Talbutal Thiamylal Thiopental Vinbarbital Vinylbital

Benzodiazepines:	Brotizolam Cinolazepam Climazolam Doxefazepam Estazolam Flunitrazepam Flurazepam Flutoprazepam Haloxazolam Loprazolam Lormetazepam Midazolam Nimetazepam Nitrazepam Quazepam Temazepam Triazolam

Carbamates:	Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate

Neuroactive Steroids:	Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Ganaxolone Hydroxydione Minaxolone Org 20599 Org 21465 Tetrahydrodeoxycorticosterone

Nonbenzodiazepines:	CL-218,872 Eszopiclone Indiplon JM-1232 Lirequinil Necopidem Pazinaclone ROD-188 Saripidem Suproclone Suriclone SX-3228 U-89843A U-90042 Zaleplon Zolpidem Zopiclone

Phenols:	Fospropofol Propofol

Piperidinediones:	Glutethimide Methyprylon Pyrithyldione Piperidione

Quinazolinones:	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164

Volatiles/gases	Acetophenone Acetylglycinamide chloral hydrate Centalun Chloral hydrate Paraldehyde

Others:	Bromide Lithium bromide Potassium bromide Sodium bromide Chloralose Clomethiazole Dichloralphenazone Etomidate Gaboxadol Loreclezole Metomidate Org 25435 Petrichloral Sulfonmethane Triclofos Valerenic acid Valerian

GABA_B
agonists

1,4-Butanediol
Aceburic acid
GABOB
GHB (Sodium oxybate)
GBL
GVL

H₁ inverse
agonists

Antihistamines:	Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Pheniramine Promethazine Propiomazine

Antidepressants	Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.

Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

α₁-Adrenergic
antagonists

Antidepressants	Serotonin antagonists and reuptake inhibitors Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin

Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

Others:	Niaprazine

α₂-Adrenergic
agonists

5-HT_2A
antagonists

Antidepressants	Serotonin antagonists and reuptake inhibitors 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:	Eplivanserin Niaprazine Pruvanserin Volinanserin

Melatonin
agonists

Orexin
antagonists

Others

Acecarbromal
Apronal
Bromisoval
Cannabidiol
- Cannabis
Carbromal
Embutramide
Evoxine
Fenadiazole
Gabapentin
Kavalactones
- Kava
Mephenoxalone
Opioids
- Oxycodone
- Morphine
  - Opium), etc.
Passion flower
Scopolamine
- Mandrake
UMB68
Valnoctamide

v t e GABA_A receptor PAMs

Alcohols	2M2B Butanol Chloralodol Chlorobutanol Ethanol (drinking alcohol) Ethchlorvynol Menthol Methanol Methylpentynol Pentanol Propanol Trichloroethanol

Barbiturates	Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Bucolome Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Prazitone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital

Benzodiazepines	Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Chlordiazepoxide Ciclotizolam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Cyprazepam Delorazepam Diazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Girisopam Halazepam Haloxazolam Iclazepam Imidazenil Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Nerisopam Nimetazepam Nitrazepam Nitrazepate Nordazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tofisopam Triazolam Triflubazam Uldazepam Zapizolam Zolazepam Zomebazam

Neuroactive steroids	Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Ganaxolone Hydroxydione Minaxolone Org 20599 Org 21465 THDOC

Nonbenzodiazepines	β-Carbolines: Abecarnil Gedocarnil SL-651,498 ZK-93423; Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone; Imidazopyridines: Alpidem 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 ELB-139 GBLD-345 L-838,417 NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 Stiripentol SX-3228 TP-003 TPA-023 TP-13 U-89843A U-90042 Y-23684

Phenols	Fospropofol Propofol Thymol

Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione

Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate

Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone

Volatiles/gases	Acetone Acetophenone Acetylglycinamide chloral hydrate Benzene Butane Butylene Centalun Chloral Chloral hydrate Chloroform Cyclopropane Desflurane Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Gasoline Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Paraldehyde Propane Propylene Sevoflurane Toluene Trichloroethylene Vinyl ether Xenon

Others	Bromide (Lithium bromide Potassium bromide Sodium bromide) Chloralose Chlormezanone Clomethiazole DEABL Etazepine Etifoxine Etomidate GABA Kavalactones (Kava) Loreclezole Metomidate Org 25,435 Petrichloral Propanidid Skullcap Stiripentol Sulfonmethane Tetronal Triclofos Trional Valeric acid Valerenic acid (Valerian)

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Crotylbarbital

See also

References