Encyprate

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;

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.

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]

References

^ Swett LR, Martin WB, Taylor JD, Everett GM, Wykes AA, Gladish YC (July 1963). "Structure-activity relations in the pargyline series". Annals of the New York Academy of Sciences. 107 (3): 891–898. Bibcode:1963NYASA.107..891S. doi:10.1111/j.1749-6632.1963.tb13332.x. PMID 13979700.
^ US 3083226, Horrom BW, Martin WB, issued 1963, assigned to Abbott Lab
^ Mitscher LA, Lednicer D (1977). The organic chemistry of drug synthesis. New York: Wiley. p. 27. ISBN 0-470-10750-2.

[1] Swett LR, Martin WB, Taylor JD, Everett GM, Wykes AA, Gladish YC (July 1963). "Structure-activity relations in the pargyline series". Annals of the New York Academy of Sciences. 107 (3): 891–898. Bibcode:1963NYASA.107..891S. doi:10.1111/j.1749-6632.1963.tb13332.x. PMID 13979700.

[2] US 3083226, Horrom BW, Martin WB, issued 1963, assigned to Abbott Lab

[isbn0-470-10750-2-3] Mitscher LA, Lednicer D (1977). The organic chemistry of drug synthesis. New York: Wiley. p. 27. ISBN 0-470-10750-2.

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