Etifelmine

Etifelmine (INN; also known as gilutensin) is a stimulant drug. It was used for the treatment of hypotension (low blood pressure).^[1]

Etifelmine

Clinical data
ATC code	none
Identifiers
IUPAC name 2-(Diphenylmethylidene)butan-1-amine
CAS Number	341-00-4
PubChem CID	68840
ChemSpider	62073 Y
UNII	1ZFB1FR98E
ChEMBL	ChEMBL2104621
CompTox Dashboard (EPA)	DTXSID70187690
Chemical and physical data
Formula	C17H19N
Molar mass	237.346 g·mol−1
3D model (JSmol)	Interactive image
SMILES C(=C(/c1ccccc1)c2ccccc2)(\CN)CC
InChI InChI=1S/C17H19N/c1-2-14(13-18)17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12H,2,13,18H2,1H3 Y Key:WNKCJOWTKXGERE-UHFFFAOYSA-N Y
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Synthesis

The base-catalyzed reaction between benzophenone (1) and butyronitrile (2) gives 2-[hydroxy(diphenyl)methyl]butanenitrile (3).^[2][3] Catalytic hydrogenation reduces the nitrile group to a primary amine giving 1,1-diphenyl-2-ethyl-3-aminopropanol (4). The tertiary hydroxyl group is dehydrated by treatment with anhydrous hydrogen chloride gas, completing the synthesis of etifelmine (5).

Synthesis of etifelmine

See also

• 2-MDP
• Pridefine