Difemetorex

Last updated
Difemetorex
Difemetorex.svg
Clinical data
Routes of
administration 		Oral
ATC code
  • none
Legal status
Legal status
  • Withdrawn
Identifiers
  • 2-[2-(diphenylmethyl)piperidin-1-yl]ethanol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H25NO
Molar mass 295.426 g·mol−1
3D model (JSmol)
  • OCCN1C(CCCC1)C(c2ccccc2)c3ccccc3

Difemetorex (INN) or diphemethoxidine (USAN) is a central nervous system (CNS) stimulant drug introduced in France in 1966 by the pharmaceutical company, Ciba-Geigy; it was briefly used as an appetite suppressant and weight loss aid into the early 1970s, sold under the brand name Cleofil. A member of the piperidine chemical class, difemetorex was described as having such a disruptive and intolerable side effect of insomnia that patient drug compliance suffered and frequency of clinical use decreased, resulting in withdrawal from the market and cessation of production, availability, accessibility, and overall recognition among related substances. It is only known to have been marketed in France, and has remained virtually non-existent in the current era. [1] [2] [3] [4] [5] [6]

Contents

Synthesis of difemetorex Difemetorex synthesis.svg
Synthesis of difemetorex

Synthesis

Alkylation of desoxypipradrol with ethylene oxide gives difemetorex. [7]

Synthesis of difemetorex Difemetorex synthesis.svg
Synthesis of difemetorex

See also

References

  1. ↑ Brudon P (1983). Médicaments pour tous en l'an 2000?: les multinationales pharmaceutiques suisses face au tiers monde : l'exemple du Mexique. France: Editions d'En bas. p. 207. ISBN   2-8290-0039-0.
  2. ↑ Isbell H, Chrusciel TL (1970). "Dependence liability of "non-narcotic" drugs". Bulletin of the World Health Organization. 43 Suppl (Suppl): 1–111. PMC   2427633 . PMID   4949109.
  3. ↑ Stepanek J, Zolliker VR (June 1971). "[Circulatory effects of the anorectic Diphemethoxidine compared with the effects of Amphetamine and Aminorex]". Archives Internationales de Pharmacodynamie et de Therapie. 191 (2): 376–99. PMID   5089225.
  4. ↑ Stepanek J (September 1972). "[Alteration of the acid-base equilibrium by the anorectic diphemethoxidine in comparison with the effect of amphetamine and aminorex]". Archives Internationales de Pharmacodynamie et de Therapie. 199 (1): 122–38. PMID   5072180.
  5. ↑ Hall JA, Morton I (1999). Concise dictionary of pharmacological agents: properties and synonyms. Kluwer Academic. ISBN   0-7514-0499-3.
  6. ↑ "The use of common stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances" (PDF). Retrieved 2010-03-23.[ dead link ]
  7. ↑ GB 861815,"New hydroxyalkyl-piperidines",issued 1961, assigned to CIBA Ltd
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