Amixetrine

Amixetrine (INN; brand name Somagest; developmental code 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]

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)

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).^[3][4] Displacement of the halogen leaving group by pyrrolidine completes the synthesis of amixetrine (4).

Synthesis of amixetrine