Amixetrine

Amixetrine

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 1-[2-(3-methylbutoxy)-2-phenylethyl]pyrrolidine
CAS Number	24622-72-8^Y
PubChem CID	71911
ChemSpider	64922^Y
UNII	7UL287YTPJ
ChEMBL	ChEMBL2104080^N
CompTox Dashboard (EPA)	DTXSID10865162
Chemical and physical data
Formula	C17H27NO
Molar mass	261.409 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O(CCC(C)C)C(c1ccccc1)CN2CCCC2
InChI 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^Y Key:ISRODTBNJUAWEJ-UHFFFAOYSA-N^Y
^NY (what is this?)  (verify)

Amixetrine (INN) (brand name Somagest; developmental code name CERM-898) is a drug that was formerly marketed in France but is now no longer sold.[1][2] 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.[1][2] The drug was first synthesized in 1969 and was introduced in France in 1972.[1][2]

Synthesis

Patent:[3] Reagent:[4]

The treatment of isoamyl alcohol (1) with styrene (2) at -10°C with dropwise addition of tert-Butyl Hypobromite [1611-82-1] gives (2-bromo-1-(isopentyloxy)ethyl)benzene [5452-50-6] (3). Displacement of the halogen leaving group by pyrrolidine completes the synthesis of amixetrine (4).

References

1. 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. 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. Finkelstein, B. L., Hu, T. (15 March 2009). "Encyclopedia of Reagents for Organic Synthesis". In John Wiley & Sons, Ltd (eds.). tert -Butyl Hypobromite. John Wiley & Sons, Ltd. pp. rb387.pub2. doi:10.1002/047084289X.rb387.pub2.