2-Carbomethoxytropinone (2-CMT) is a commonly used organicintermediate in the synthesis of cocaine and its analogues. As of at least 1999 no reaction pathway has been discovered that synthesizes cocaine-like compounds without utilizing the reduction of 2-carbomethoxytropinone. The structure of cocaine was discovered by Richard Willstätter in 1898 after he synthesized it from 2-carbomethoxytropinone. Although it was originally believed that 2-CMT in nature was ultimately derived from ornithine and acetic acid, subsequent research has indicated other pathways exist for the biosynthesis of 2-CMT. A β-keto ester, 2-carbomethoxytropinone exists in equilibrium with its keto–enol tautomer.
^Findlay, Stephen P. (1957). "Concerning 2-Carbomethoxytropinone*". The Journal of Organic Chemistry22 (11): 1385. doi:10.1021/jo01362a022.
^Simoni, Daniele; Roberti, Marinella; Andrisano, Vincenza; Manferdini, Monica; Rondanin, Riccardo; Invidiata, Francesco Paolo (1999). "Two-carbon bridge substituted cocaines: Enantioselective synthesis, attribution of the absolute configuration and biological activity of novel 6- and 7-methoxylated cocaines". Il Farmaco54 (5): 275–87. doi:10.1016/S0014-827X(99)00027-0. PMID10418122.
^Humphrey, Andrew J.; O'Hagan, David (2001). "Tropane alkaloid biosynthesis. A century old problem unresolved". Natural Product Reports18 (5): 494–502. doi:10.1039/b001713m. PMID11699882.
^Findlay, Stephen P. (1954). "The Three-dimensional Structure of the Cocaines. Part I. Cocaine and Pseudococaine". Journal of the American Chemical Society76 (11): 2855. doi:10.1021/ja01640a001.
^Leete, Edward (1983). "Chemistry of the tropane alkaloids. 33. 2-Carbomethoxy-3-tropinone: An advanced intermediate in the biosynthesis of cocaine". Journal of the American Chemical Society105 (22): 6727. doi:10.1021/ja00360a038.
^Leete, Edward.; Kim, Sung Hoon. (1988). "A revision of the generally accepted hypothesis for the biosynthesis of the tropane moiety of cocaine". Journal of the American Chemical Society110 (9): 2976. doi:10.1021/ja00217a051.