Methylpentynol

Methylpentynol
Clinical data
Trade names	Oblivon
Routes of; administration	By mouth
ATC code	N05CM15 (WHO) ;
Legal status
Legal status	Withdrawn;
Identifiers
	IUPAC name 3-methylpent-1-yn-3-ol;
CAS Number	77-75-8 ;
PubChem CID	6494;
ChemSpider	21106516 ;
UNII	B017BC5B1N;
CompTox Dashboard (EPA)	DTXSID5021756 ;
ECHA InfoCard	100.000.960
Chemical and physical data
Formula	C6H10O
Molar mass	98.145 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(C)(C#C)O;
	InChI InChI=1S/C6H10O/c1-4-6(3,7)5-2/h1,7H,5H2,2-3H3 ; Key:QXLPXWSKPNOQLE-UHFFFAOYSA-N ;
	(what is this?)

Methylpentynol (Methylparafynol, Dormison, Atemorin, Oblivon) is a tertiary hexanol with hypnotic/sedative and anticonvulsant effects and an exceptionally low therapeutic index. It was discovered by Bayer in 1913^[1] 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.^[2]^[3]^[4]^[5]^{[excessive citations]}

The drug was marketed again in the United States, Europe and elsewhere from 1956 well into the 1960s as a rapid-acting sedative; The drug was quickly overshadowed at that point by benzodiazepines and is no longer sold anywhere.^[6]

Synthesis[]

Methylpentynol is prepared by reaction of butanone (MEK) with sodium acetylide. This reaction must be done in anhydrous conditions and in an inert atmosphere.

References[]

^ 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

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[1] DE patent 289800, "Verfahren zur Darstellung der Oxyalkylderivate von Kohlenwasserstoffen", issued 1913-11-30, assigned to Bayer, Leverkusen

[2] 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.

[3] 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.

[4] 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.

[5] 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.

[6] Hines RD (2002). The Pursuit of Oblivion. p. 327.

[7] DE 959485, Grimene W, Emde H, issued 1957

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v t GABA_A receptor positive modulators
Alcohols	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	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 Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT-201 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	Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Luteolin Skullcap constituents (e.g., baicalin) Wogonin
Imidazoles	Etomidate Metomidate Propoxate
Kava constituents	Desmethoxyyangonin Kavain Methysticin Yangonin
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal
Neuroactive steroids	Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Pregnanolone (eltanolone) Progesterone Renanolone 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 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil (Ro41-3696) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine 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 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 Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines (e.g., dihydroergocryptine, , dihydroergotamine, ergoloid (dihydroergotoxine)) Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Niacin Niacinamide Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, ) Unsorted benzodiazepine site positive modulators: α-Pinene
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

Clinical data


Trade names	Oblivon
Routes of administration	By mouth
ATC code	N05CM15 (WHO)
Legal status
Legal status	Withdrawn
Identifiers
IUPAC name 3-methylpent-1-yn-3-ol
CAS Number	77-75-8^Y
PubChem CID	6494
ChemSpider	21106516^N
UNII	B017BC5B1N
CompTox Dashboard (EPA)	DTXSID5021756
ECHA InfoCard	100.000.960
Chemical and physical data
Formula	C₆H₁₀O
Molar mass	98.145 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCC(C)(C#C)O
InChI InChI=1S/C6H10O/c1-4-6(3,7)5-2/h1,7H,5H2,2-3H3^N Key:QXLPXWSKPNOQLE-UHFFFAOYSA-N^N
^NY (what is this?)

Methylpentynol

Synthesis[]

See also[]

References[]