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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. [1] [2] [3] [4]
Ethinamate (1-ethynylcyclohexanone carbamate) is synthesized by combining acetylene with cyclohexanone to make 1-ethynylcyclohexanol, and then transforming this into a carbamate by the subsequent reaction with phosgene, and later with ammonia. Some lithium metal or similar is used to make the acetylene react with the cyclohexanone in the first ...
Chemical formula Synonyms CAS number C 10 H 16 N 2 O 8: Ethylenediaminetetraacetic acid (EDTA): 6381–92–6 C 12 H 22 O 11: sucrose: 57–50–1 C 18 H 29 O 3 S: sodium dodecyl benzenesulfonate: 2155–30–0
CAS Number. 100-49-2 ... 19 °C (66 °F) [1] Boiling point: 187–188 °C (369–370 °F) [3] Solubility in water. small in water [4] Hazards Flash point:
[1] It is produced industrially by the hydrogenation of cyclohexanone in the presence of hydrogen sulfide over a metal sulfide catalyst: C 6 H 10 O + H 2 S + H 2 → C 6 H 11 SH + H 2 O. It is also obtained by the addition of hydrogen sulfide to cyclohexene in the presence of nickel sulfide. [2]
Cyclohexanol is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: [5]. 2 C 6 H 12 + O 2 → 2 C 6 H 11 OH. This process coforms cyclohexanone, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid.
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The Hay coupling is variant of the Glaser coupling. It relies on the TMEDA complex of copper(I) chloride to activate the terminal alkyne. Oxygen (air) is used in the Hay variant to oxidize catalytic amounts of Cu(I) to Cu(II) throughout the reaction, as opposed to a stoichiometric amount of Cu(II) used in the Eglington variant. [7]