Encyprate

Encyprate is a monoamine oxidase inhibitor (MAOI) agent that was developed for use in the treatment of depression. It is an irreversible inhibitor of the MAO enzyme because it is agent that can form covalent bonds with the active site. As such, it is sometimes referred to as a “suicide inactivator” of MAO. It was invented by Bruce Horrom of Abbott in the 1960s by structure activity studies on pargyline.^[1] Although it is not known to have ever been used in the clinic, it is an example of the heritage of agents that were developed at that time.

Encyprate

Clinical data
Other names	MO-1255
Identifiers
IUPAC name ethyl N-benzyl-N-cyclopropylcarbamate
CAS Number	2521-01-9
PubChem CID	17298
ChemSpider	16368
UNII	26991ZCA4G
KEGG	D03993
ChEMBL	ChEMBL2104204
CompTox Dashboard (EPA)	DTXSID90179870
ECHA InfoCard	100.209.661
Chemical and physical data
Formula	C13H17NO2
Molar mass	219.284 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCOC(=O)N(CC1=CC=CC=C1)C2CC2
InChI InChI=1S/C13H17NO2/c1-2-16-13(15)14(12-8-9-12)10-11-6-4-3-5-7-11/h3-7,12H,2,8-10H2,1H3 Key:OGXBVBBMMWSZJO-UHFFFAOYSA-N

Synthesis

Encyprate synthesis

The condensation between cyclopropylamine [765-30-0] (1) and benzaldehyde [100-52-7] (2) gives N-benzylidenecyclopropylamine [3187-77-7] (3). The reduction of the Schiff-base gives N-benzylcyclopropylamine [13324-66-8] (4). Urethane formation with ethyl chloroformate [541-41-3] (5) completes the synthesis of encyprate (6).^[2][3]