benzoylmethylecgonine

is a crystalline tropane alkaloid, and is an appetite suppressant and topical anesthetic - This is more commonly known as cocaine. Cocaine inhibits the re-uptake of dopamine, norepinephrine, and seratonin. Meaning, when these three chemicals are realesed in the brain, the cocaine molecules inhibit the ability of the nueron to reabsorb the chemicals that cause pleasure in the body.
 * Benzoylmethylecgonine (C 17 H 21 NO 4 )**

Biosynthesis of N-methyl-pyrrolinium cation
The biosynthesis begins with L- Glutamine, which is derived to L- ornithine in plants. The major contribution of L-ornithine and L- arginine as a precursor to the tropane ring was confirmed by Edward Leete. Ornithine then undergoes a Pyridoxal phosphate -dependent decarboxylation to form putrescine. In animals, however, the urea cycle derives putrescine from ornithine. L-ornithine is converted to L-arginine, which is then decarboxylated via PLP to form agmatine. Hydrolysis of the imine derives // N // -carbamoylputrescine followed with hydrolysis of the urea to form putrescine. The separate pathways of converting ornithine to putrescine in plants and animals have converged. A SAM-dependent // N // -methylation of putrescine gives the // N // -methylputrescine product, which then undergoes oxidative deamination by the action of diamine oxidase to yield the aminoaldehyde. Schiff base formation confirms the biosynthesis of the // N // -methyl-Δ1-pyrrolinium cation.

Biosynthesis of cocaine
The additional carbon atoms required for the synthesis of cocaine are derived from acetyl-CoA, by addition of two acetyl-CoA units to the //N//-methyl-Δ1-pyrrolinium cation. The first addition is a Mannich -like reaction with the enolate anion from acetyl-CoA acting as a nucleophile towards the pyrrolinium cation. The second addition occurs through a Claisen condensation. This produces a racemic mixture of the 2-substituted pyrrolidine, with the retention of the thioester from the Claisen condensation. In formation of tropinone from racemic ethyl [2,3-13C2]4(Nmethyl-2-pyrrolidinyl)-3-oxobutanoate there is no preference for either stereoisomer. In the biosynthesis of cocaine, however, only the (S)-enantiomer can cyclize to form the tropane ring system of cocaine. The stereoselectivity of this reaction was further investigated through study of prochiral methylene hydrogen discrimination. This is due to the extra chiral center at C-2. This process occurs through an oxidation, which regenerates the pyrrolinium cation and formation of an enolate anion, and an intramolecular Mannich reaction. The tropane ring system undergoes hydrolysis, SAM-dependent methylation, and reduction via NADPH for the formation of methylecgonine. The benzoyl moiety required for the formation of the cocaine diester is synthesized from phenylalanine via cinnamic acid. Benzoyl-CoA then combines the two units to form cocaine.

Cocaine is the second most popular illegal recreational drug in the U.S. and the U.S. is the world's largest consumer of cocaine. Cocaine is commonly used in middle to upper class communities. It is also popular amongst college students, as a party drug. The National Household Survey on Drug Abuse (NHSDA) reported in 1999 that cocaine was used by 3.7 million Americans, or 1.7% of the household population age 12 and older. Estimates of the current number of those who use cocaine regularly (at least once per month) vary, but 1.5 million is a widely accepted figure within the research community. The 1999 Monitoring the Future (MTF) survey found the proportion of American students reporting use of powdered cocaine rose during the 1990s. In 1991, 2.3% of eighth-graders stated that they had used cocaine in their lifetime. This figure rose to 4.7% in 1999. For the older grades, increases began in 1992 and continued through the beginning of 1999. Between those years, lifetime use of cocaine went from 3.3% to 7.7% for tenth-graders and from 6.1% to 9.8% for high school seniors. Lifetime use of crack cocaine, according to MTF, also increased among eighth-, tenth-, and twelfth-graders, from an average of 2% in 1991 to 3.9% in 1999.
 * Uses in the United States**