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ly prescribed as a hypnotic for the short term treatment of insomnia the drug has a rapid onset of action a short elimination half life of around 2 5 hours and a correspondingly brief duration of effect prolonged use leads to drug tolerance drug dependence and diminished efficacy after seven days of continuous use 3 availability edit ethinamate was introduced by german drug company schering ag in 1957 marketed as a sleeping pill with a reduced risk of fatality in drug overdose compared to barbiturate overdose ethinamate was commonly prescribed in germany the united states australia canada the netherlands and much dubious discuss clarification needed of europe 2 4 ethinamate is not known to be available in any country despite being available in the u s until 1982 ethinamate largely fell out of favor by the 1960s as contemporary novel sedatives were viewed as safer alternatives including methaqualone ethchlorvynol glutethimide methyprylon meprobamate and by the 1960s chlordiazepoxide and diazepam recognition edit in the united states ethinamate is now primarily associated with the death of elvis presley as it was listed among multiple sedatives detected in toxicology reports leading forensic expert cyril wecht to emphasized the important role of polypharmacy in the case 5 toxicity and overdose edit ethinamate debuted nearly at the same time as methyprylon and other nonbarbiturate soporifics including ethchlorvynol and glutethimide were being developed and released continuously supratherapeutic dosing of 3 000 mg nearly seven fold a therapeutic dose induced a temporary loss of consciousness or comatose state but resulted in full recovery activated charcoal may reduce absorption if administered early and hemodialysis can be considered in severe cases citation needed dubious discuss adverse effects and safety in pregnancy edit common side effects at therapeutic doses are gastrointestinal upset nausea vomiting gastrointestinal upset rare reactions indicative of hypersensitivity involve thrombocytopenia purpura fever and various skin rashes clarification needed 4 the drug is classified as pregnancy category c and is not recommended during pregnancy or breastfeeding due to insufficient evidence regarding potential teratogenic effects animal studies suggest porphyrinogenic potential in vivo citation needed chemistry and synthesis edit the compound is synthesized by reacting acetylene with cyclohexanone to form 1 ethynylcyclohexanol this intermediate is then converted into a carbamate through reaction with phosgene and ammonia small amounts of lithium or similar reagents may be used to facilitate the initial acetylene reaction 6 7 ethinamate whose molecular structure is known as 1 ethynylcyclohexane carbamate is an odorless white crystalline powder it is typically formulated as 500 mg tablets for oral administration with an adult dose of one tablet at bedtime two tablets may be taken if necessary children are more prone to paradoxical effects and the drug is not indicated for individuals under 18 citation needed the compound is synthesized by reacting acetylene with cyclohexanone to form 1 ethynylcyclohexanol this intermediate is then converted into a carbamate through reaction with phosgene and ammonia small amounts of lithium or similar reagents may be used to facilitate the initial acetylene reaction 6 7 after ingestion ethinamate is metabolized to the active compound 4 hydroxyethinamate which is eliminated in urine with a half life of approximately 2 5 hours 3 references edit anvisa 31 march 2023 rdc nº 784 listas de substâncias entorpecentes psicotrópicas precursoras e outras sob controle especial collegiate board resolution no 784 lists of narcotic psychotropic precursor and other substances under special control in brazilian portuguese diário oficial da união published 4 april 2023 archived from the original on 3 august 2023 retrieved 16 august 2023 1 2 victoria museum of pharmacology valamin at the victoria museum of pharmacy retrieved 18 january 2026 1 2 ethinamate valmid valamin overview pubchem retrieved 2 may 2025 1 2 lowry wt garriot jc 1979 ethinamate forensic toxicology controlled substances and dangerous drugs boston ma springer us p 215 isbn 978 1 4684 3444 6 cole j thompson c 2 august 2017 the death of elvis memphis magazine memphis magazine retrieved 4 september 2025 1 2 us 2816910 pfeiffer h junkman k esters of carbamic acid and a method of making same issued 17 december 1957 assigned to schering ag 1 2 de 1021843 emde h grimme w verfahren zur herstellung des allophanats des 1 aethinylcyclohexanols 1 issued 2 january 1958 assigned to rheinpreussen ag v t e 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 clobazam 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 1 4 butanediol 4 fluorophenibut aceburic acid baclofen gabob ghb sodium oxybate gbl gvl jzp 386 phenibut tolibut valiloxybate xw 10172 h 1 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 α 2 adrenergic clonidine detomidine dexmedetomidine lofexidine medetomidine romifidine tasipimidine tizanidine xylazine 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 agomelatine melatonin ramelteon tasimelteon orexin daridorexant lemborexant suvorexant α 2 δ vdcc atagabalin baclofen gabapentin gabapentin enacarbil mirogabalin phenibut pregabalin others cannabinoids e g cannabis tetrahydrocannabinol dronabinol nabilone cannabidiol zenivol chlorophenylalkyldiols fenpentadiol metaglycodol phenaglycodol diethylpropanediol metamizil evoxine fenadiazole gaba reuptake inhibitors e g tiagabine guaifenesin related muscle relaxants chlorphenesin mephenesin mephenoxalone metaxalone methocarbamol midaflur opioids e g morphine passion flower pellotine phemerazole scopolamine serotonin precursors e g tryptophan 5 hydroxytryptophan 5 htp oxitriptan trazodone tributyrin umb68 valnoctamide 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 methallatal 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 neurosteroids acebrochol allopregnanolone brexanolone alfadolone alfaxalone 3α androstanediol androstenol androsterone certain anabolic androgenic steroids cholesterol cortisol hydrocortisone dhdoc 3α dhp 5α dhp 5β dhp dht etiocholanolone etx 155 ganaxolone hydroxydione lpcn 1154 minaxolone nora 520 org 20599 org 21465 p1 185 posovolone prax 114 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 axs 17 baer 101 azd 7325 cgs 8216 cgs 9896 cgs 13767 cgs 20625 cl 218 872 cp 615 003 ctp 354 elb 139 enx 102 tpa 023b gbld 345 imepitoin jm 1232 l 838 417 lirequinil ro41 3696 miltirone rosmariquinone ns 2664 ns 2710 ns 11394 ns 11821 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 nezavist dcuk oet nicotinic acid nicotinamide ntx 1955 ro 7308480 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...