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ylparafynol trade names dormison atemorin oblivon is a tertiary pentynol with hypnotic sedative and anticonvulsant effects and an exceptionally low therapeutic index it was discovered by bayer in 1913 2 and was used shortly thereafter for the treatment of insomnia but its use was quickly phased out in response to newer drugs with far more favorable safety profiles 3 4 5 the drug was marketed again in the united states europe and elsewhere from 1956 well into the 1960s as a rapid acting sedative 6 the drug was quickly overshadowed at that point by benzodiazepines and is no longer sold anywhere 7 synthesis edit methylpentynol is prepared by reaction of butanone mek with sodium acetylide in liquid ammonia this reaction must be done in anhydrous conditions and in an inert atmosphere applications edit as building block in the synthesis of phthalofyne 1 2 benzenedicarboxylic acid mono 1 ethyl 1 methyl 2 propynyl ester 131 67 9 anansiol 1 ethyl 1 methylprop 2 ynyl carbamate 302 66 9 bason 2 bromoethynyl 2 butanol 2028 52 6 see also edit clocental 8 ethchlorvynol references edit anvisa 2023 03 31 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 2023 04 04 archived from the original on 2023 08 03 retrieved 2023 08 16 de patent 289800 verfahren zur darstellung der oxyalkylderivate von kohlenwasserstoffen issued 1913 11 30 assigned to bayer leverkusen hirsh hl orsinger wh january 1952 methylparafynol a new type hypnotic preliminary report on its therapeutic efficacy and toxicity american practitioner and digest of treatment 3 1 23 6 pmid 14903452 schaffarzick rw brown bj december 1952 the anticonvulsant activity and toxicity of methylparafynol dormison and some other alcohols science 116 3024 663 5 bibcode 1952sci 116 663s doi 10 1126 science 116 3024 663 pmid 13028241 herz a march 1954 a new type of hypnotic unsaturated tertiary carbinols experimental studies on therapeutic use of 3 methyl pentin ol 3 methylparafynol arzneimittel forschung 4 3 198 9 pmid 13159700 weaver lc alexander wm abreu be april 1961 anticonvulsant activity of compounds related to methylparafynol archives internationales de pharmacodynamie et de therapie 131 116 22 pmid 13783544 hines rd 2002 the pursuit of oblivion p 327 de 959485 grimene w emde h issued 1957 v t e alcohols by consumption alcohols found in alcoholic drinks 1 propanol 2 methyl 1 butanol ethanol isoamyl alcohol isobutanol phenethyl alcohol tert amyl alcohol tert butyl alcohol tryptophol medical alcohol ethchlorvynol methylpentynol methanol poisoning ethanol toxic alcohols isopropyl alcohol methanol primary alcohols 1 methanol 4 methylcyclohexanemethanol aminomethanol cyclohexylmethanol methoxymethanol methylazoxymethanol trifluoromethanol ethanol 1 aminoethanol 2 2 2 trichloroethanol 2 2 2 trifluoroethanol 2 2 ethoxyethoxy ethanol 2 2 methoxyethoxy ethanol 2 2 methoxyethoxy ethanol 2 butoxyethanol 2 chloroethanol 2 ethoxyethanol 2 fluoroethanol 2 mercaptoethanol 2 methoxyethanol aminoethylethanolamine diethylethanolamine dimethylethanolamine ethanol ethanolamine n n diisopropylaminoethanol n methylethanolamine phenoxyethanol tribromoethanol butanol 2 methyl 1 butanol isobutanol n butanol straight chain saturated c 1 c 9 methanol ethanol 1 propanol 1 butanol 1 pentanol 1 hexanol 1 heptanol 1 octanol capryl 1 nonanol pelargonic straight chain saturated c 10 c 19 1 decanol capric 1 undecanol hendecyl 1 dodecanol lauryl 1 tridecanol 1 tetradecanol myristyl 1 pentadecanol 1 hexadecanol cetyl palmityl 1 heptadecanol 1 octadecanol stearyl 1 nonadecanol straight chain saturated c 20 c 29 1 icosanol arachidyl 1 heneicosanol 1 docosanol behenyl 1 tricosanol 1 tetracosanol lignoceryl 1 pentacosanol 1 hexacosanol ceryl 1 heptacosanol 1 octacosanol cluytyl montanyl 1 nonacosanol straight chain saturated c 30 c 39 1 triacontanol melissyl myricyl 1 hentriacontanol 1 dotriacontanol lacceryl 1 tritriacontanol 1 tetratriacontanol geddyl 1 pentatriacontanol 1 hexatriacontanol 1 heptatriacontanol 1 octatriacontanol 1 nonatriacontanol straight chain saturated c 40 c 49 1 tetracontanol 1 hentetracontanol 1 dotetracontanol 1 tritetracontanol 1 tetratetracontanol 1 pentatetracontanol 1 hexatetracontanol 1 heptatetracontanol 1 octatetracontanol 1 nonatetracontanol 2 ethylhexanol allyl alcohol anisyl alcohol benzyl alcohol cinnamyl alcohol crotyl alcohol furfuryl alcohol isoamyl alcohol neopentyl alcohol nicotinyl alcohol perillyl alcohol phenethyl alcohol prenol propargyl alcohol salicyl alcohol tryptophol vanillyl alcohol veratrole alcohol secondary alcohols 2 1 phenylethanol 2 butanol 2 deoxyerythritol 2 heptanol 3 heptanol 2 hexanol 3 hexanol 3 methyl 2 butanol 2 nonanol 2 octanol 2 pentanol 3 pentanol cyclohexanol cyclopentanol cyclopropanol diphenylmethanol isopropanol pinacolyl alcohol pirkle s alcohol propylene glycol methyl ether tertiary alcohols 3 2 methyl 2 pentanol 2 methylheptan 2 ol 2 methylhexan 2 ol 3 methyl 3 pentanol 3 methyloctan 3 ol diacetone alcohol ethchlorvynol methylpentynol nonafluoro tert butyl alcohol tert amyl alcohol tert butyl alcohol triphenylethanol triphenylmethanol hydric alcohols monohydric alcohols methanol c 1 ethanol c 2 isopropanol c 3 1 butanol c 4 1 pentanol c 5 cetyl alcohol c 16 dihydric alcohols ethylene glycol propylene glycol trihydric alcohols glycerol polyhydric alcohols sugar alcohols pentaerythritol ethylene glycol c 2 glycerol propylene glycol c 3 erythritol threitol c 4 xylitol c 5 mannitol sorbitol c 6 volemitol c 7 amyl alcohols 2 2 dimethylpropan 1 ol 2 methylbutan 1 ol 2 methylbutan 2 ol 3 methylbutan 1 ol 3 methylbutan 2 ol pentan 1 ol pentan 2 ol pentan 3 ol aromatic alcohols benzyl alcohol 2 4 dichlorobenzyl alcohol 3 nitrobenzyl alcohol saturated fatty alcohols cetostearyl alcohol decanol lauryl alcohol myristyl alcohol nonanol octanol tridecanol undecanol branched and unsaturated fatty alcohols 3 methyl 3 pentanol erucyl alcohol linolenyl alcohol linoleyl alcohol oleyl alcohol palmitoleyl alcohol tert amyl alcohol tert butyl alcohol sugar alcohols c 1 c 7 methylene glycol c 1 ethylene glycol c 2 glycerol c 3 erythritol c 4 threitol c 4 arabitol c 5 ribitol c 5 xylitol c 5 mannitol c 6 sorbitol c 6 galactitol c 6 iditol c 6 volemitol c 7 deoxy sugar alcohols fucitol cyclic sugar alcohols inositol glycylglycitols maltitol lactitol isomalt maltotriitol maltotetraitol polyglycitol terpene alcohols monoterpene alcohols borneol citronellol geraniol linalool menthol nerol rhodinol terpineol sesquiterpene alcohols bisabolol farnesol nerolidol patchoulol diterpene alcohols phytol dialcohols 1 3 butanediol 1 4 butanediol 1 5 pentanediol 2 methyl 2 propyl 1 3 propanediol diethylpropanediol ethylene glycol trialcohols glycerol sterols cholesterol ergosterol lanosterol β sitosterol stigmasterol fluoroalcohols 1 3 difluoro 2 propanol 2 2 2 trifluoroethanol 2 fluoroethanol nonafluoro tert butyl alcohol trifluoromethanol preparations substitution of haloalkane carbonyl reduction ether cleavage hydrolysis of epoxide hydration of alkene ziegler process reactions deprotonation protonation alcohol oxidation glycol cleavage nucleophilic substitution fischer speier esterification williamson ether synthesis elimination reaction nucleophilic substitution of carbonyl group friedel crafts alkylation nucleophilic conjugate addition transesterification category 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 ana...
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