1-Ethynylcyclohexanol - Misplaced Pages

Chemical compound Pharmaceutical compound

1-Ethynylcyclohexanol
Identifiers

IUPAC name 1-ethynylcyclohexan-1-ol
CAS Number	78-27-3
PubChem CID	6525
ChemSpider	6277
UNII	6RV04025EH
ChEMBL	ChEMBL394631
CompTox Dashboard (EPA)	DTXSID0021757
ECHA InfoCard	100.001.001
Chemical and physical data
Formula	C₈H₁₂O
Molar mass	124.183 g·mol
3D model (JSmol)	Interactive image
Melting point	30–33 °C (86–91 °F)
SMILES C#CC1(CCCCC1)O
InChI InChI=1S/C8H12O/c1-2-8(9)6-4-3-5-7-8/h1,9H,3-7H2 Key:QYLFHLNFIHBCPR-UHFFFAOYSA-N

1-Ethynylcyclohexanol (ECX) is an alkynyl alcohol derivative which is both a synthetic precursor to, and an active metabolite of the tranquilizer ethinamate, and has similar sedative, anticonvulsant and muscle relaxant effects. It has been sold as a designer drug, first being identified in the UK in March 2012.

Preparation

1-Ethynylcyclohexanol can be prepared from cyclohexanone by the reacting it with sodium acetylide in liquid ammonia, followed by an acidic work-up.

References

Levina RY, Vinogradova EU (1936). "Action of sodium acetylide on cyclic ketones. I. Synthesis of 1-ethynylcyclohexanol". Zhurnal Prikladnoi Khimii. 9. Sankt-Peterburg, Russian Federation: 1299–1302. ISSN 0044-4618.
Verkruijsse HD, Graaf WD, Brandsma L (February 1988). "An efficient and quick laboratory scale method for the ethynylation of some aliphatic and cycloaliphatic carbonyl compounds". Synthetic Communications. 18 (2): 131–4. doi:10.1080/00397918808077336.
Nazarov IN, Kotlyarevskii IL, Ryabchenko VF (1953). "Acetylene derivatives. CLX. Condensation of aldehydes and ketones with acetylene under pressure. New method of synthesis of acetylenic alcohols". Zhurnal Obshchei Khimii. 23: 1900–1904. ISSN 0044-460X.
"Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA (New drugs in Europe, 2012)" (PDF). Lisbon: EMCDDA. May 2013.
Saunders JH, Schreiber RS, Jenner EL (1949). "1-ETHYNYLCYCLOHEXANOL". Organic Syntheses. 29: 47. doi:10.15227/orgsyn.029.0047.

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 C₁ — C₉	Methanol Ethanol 1-Propanol 1-Butanol 1-Pentanol 1-Hexanol 1-Heptanol 1-Octanol (capryl) 1-Nonanol (pelargonic)
Straight-chain saturated C₁₀ — C₁₉	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 C₂₀ — C₂₉	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 C₃₀ — C₃₉	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 C₄₀ — C₄₉	1-Tetracontanol 1-Hentetracontanol 1-Dotetracontanol 1-Tritetracontanol 1-Tetratetracontanol 1-Pentatetracontanol 1-Hexatetracontanol 1-Heptatetracontanol 1-Octatetracontanol 1-Nonatetracontanol

Secondary
alcohols (2°)

Propylene glycol methyl ether

Tertiary
alcohols (3°)

Hydric alcohols

Monohydric alcohols	Methanol (C₁) Ethanol (C₂) Isopropanol (C₃) 1-Butanol (C₄) 1-Pentanol (C₅) Cetyl alcohol (C₁₆)
Dihydric alcohols	Ethylene glycol Propylene glycol
Trihydric alcohols	Glycerol
Polyhydric alcohols (sugar alcohols)	Pentaerythritol Ethylene glycol (C₂) Glycerol, Propylene glycol (C₃) Erythritol, Threitol (C₄) Xylitol (C₅) Mannitol, Sorbitol (C₆) Volemitol (C₇)

Amyl alcohols

Aromatic alcohols

Saturated
fatty alcohols

Branched and
unsaturated
fatty alcohols

Sugar alcohols

C₁ — C₇	Methylene glycol (C₁) Ethylene glycol (C₂) Glycerol (C₃) Erythritol (C₄) Threitol (C₄) Arabitol (C₅) Ribitol (C₅) Xylitol (C₅) Mannitol (C₆) Sorbitol (C₆) Galactitol (C₆) Iditol (C₆) Volemitol (C₇)
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

Trialcohols

Glycerol

Sterols

Fluoroalcohols

Preparations

Reactions

Category

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
Neuroactive steroids	Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Hydroxydione Minaxolone Progesterone
Nonbenzodiazepines	Eszopiclone Indiplon Lirequinil Necopidem Pazinaclone Saripidem Suproclone Suriclone Zaleplon Zolpidem Zopiclone
Phenols	Propofol
Piperidinediones	Glutethimide Methyprylon Pyrithyldione Piperidione
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 Kavalactones Loreclezole Paraldehyde Petrichloral Sulfonylalkanes Sulfonmethane (sulfonal) Tetronal Trional Triclofos Sesquiterpene Isovaleramide Isovaleric acid Valerenic acid

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

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Categories:

Preparation

See also

References