1-Ethynylcyclohexanol

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]

1-Ethynylcyclohexanol
Identifiers
IUPAC name
  • 1-ethynylcyclohexan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.001
Chemical and physical data
FormulaC8H12O
Molar mass124.183 g·mol−1
3D model (JSmol)
Melting point30–33 °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

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. Levina RY, Vinogradova EU (1936). "Action of sodium acetylide on cyclic ketones. I. Synthesis of 1-ethynylcyclohexanol". Zhurnal Prikladnoi Khimii. Sankt-Peterburg, Russian Federation. 9: 1299–1302. ISSN 0044-4618.
  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. 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. "Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA (New drugs in Europe, 2012)" (PDF). Lisbon: EMCDDA. May 2013.
  5. Saunders JH, Schreiber RS, Jenner EL (1949). "1-ETHYNYLCYCLOHEXANOL". Organic Syntheses. 29: 47. doi:10.15227/orgsyn.029.0047.
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