Ciclafrine

Ciclafrine (INN) is a sympathomimetic phenethylamine and antihypertensive that was never marketed.[1][2]

Ciclafrine
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 3-(1-Oxa-4-azaspiro[4.6]undec-2-yl)phenol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H21NO2
Molar mass247.338 g·mol−1
3D model (JSmol)
SMILES
  • c1cc(cc(c1)O)C2CNC3(O2)CCCCCC3
InChI
  • InChI=1S/C15H21NO2/c17-13-7-5-6-12(10-13)14-11-16-15(18-14)8-3-1-2-4-9-15/h5-7,10,14,16-17H,1-4,8-9,11H2
  • Key:AJNAKEPPGKJNKU-UHFFFAOYSA-N

Synthesis

Ciclafrine can be prepared by the reaction of norfenefrine with cycloheptanone.[3]

Ciclafrine synthesis

References

  1. Ganellin CR, Triggle DJ (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 586–. ISBN 978-0-412-46630-4.
  2. Korolkovas A (1988). Essentials of medicinal chemistry. John Wiley & Sons, Incorporated. p. 405. ISBN 978-0-471-88356-2.
  3. DE 2336746, Satzinger, Gerhard & Herrmann, Manfred, "2-Hydroxyphenyl-1-oxa-4-azaspiro-alkan-Derivate [2-Hydroxyphenyl-1-oxa-4-azaspiro-alkane derivatives]", published 1975-02-13, assigned to Gödecke AG


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