Amixetrine

Amixetrine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 1-[2-(3-methylbutoxy)-2-phenylethyl]pyrrolidine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H27NO
Molar mass261.409 g·mol−1
3D model (JSmol)
  • O(CCC(C)C)C(c1ccccc1)CN2CCCC2
  • InChI=1S/C17H27NO/c1-15(2)10-13-19-17(14-18-11-6-7-12-18)16-8-4-3-5-9-16/h3-5,8-9,15,17H,6-7,10-14H2,1-2H3 checkY
  • Key:ISRODTBNJUAWEJ-UHFFFAOYSA-N checkY
 X markNcheckY (what is this?)  (verify)

Amixetrine (INN; brand name Somagest; developmental code CERM-898) is a drug that was formerly marketed in France but is now no longer sold. According to various sources it has been said to be an anti-inflammatory, antidepressant, antispasmodic, anticholinergic, antihistamine, and antiserotonergic, but its definitive indications and pharmacology are unclear. The drug was first synthesized in 1969 and was introduced in France in 1972.

Synthesis

The treatment of isoamyl alcohol (1) with styrene (2) at −10 °C with dropwise addition of tert-butyl hypobromite gives (2-bromo-1-(isopentyloxy)ethyl)benzene (3). Displacement of the halogen leaving group by pyrrolidine completes the synthesis of amixetrine (4).

Synthesis of amixetrine

References

  1. 1 2 3 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 80–. ISBN 978-1-4757-2085-3.
  2. 1 2 3 William Andrew Publishing (22 October 2013). "Amixetrine Hydrochloride". Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 285–. ISBN 978-0-8155-1856-3.
  3. ↑ GB 1253818 idem Mauvernay Roland Yves, Norbert Busch, DE1811767A1 (1969 to Ct Europ De Rech S Mauvernay)
  4. ↑ "-Butyl Hypobromite". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. 2009. doi:10.1002/047084289X.rb387.pub2. ISBN 978-0-470-84289-8.