1-Ethynylcyclohexanol

1-Ethynylcyclohexanol

1-Ethynylcyclohexanol

Chemical compound

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]

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Preparation

Synthesis of 1-ethynylcyclohexanol from cyclohexanone.

1-Ethynylcyclohexanol can be prepared from cyclohexanone by the reacting it with sodium acetylide in liquid ammonia, followed by an acidic work-up.[5]

See also

References

  1. [1]
    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.
  2. [2]
    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.
  3. [3]
    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.
  4. [4]
    "Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA (New drugs in Europe, 2012)" (PDF). Lisbon: EMCDDA. May 2013.
  5. [5]
    Saunders JH, Schreiber RS, Jenner EL (1949). "1-ETHYNYLCYCLOHEXANOL". Organic Syntheses. 29: 47. doi:10.15227/orgsyn.029.0047.
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