Anhydroecgonine

Tropidine CgHj3N —Tropilidene C,Hg (S-cyclo Heptatriene) Anhydroecgonine C9H13O2N —> -eycloHeptatrienccaTboxylic acid CjHgOj... 

Anhalonium alkaloids, pharmacology, 160 Anhalonium spp., 154 Anhydroberberilic acid, 332 Anhydroecgonine, 97 Anhydrolupinine, 120 Anhydroxatine, 770 Anisomeles malabaTica, 779 Af-(2-p-Anisylethyl)-AT-methyl-cinnamide, 330, 631 Annona anibotay, 371 Annotinine, 752, 753, 755 Anodmine, 47 Anolobine, 317... 

S1 C10H15NO2 94 2,3-Dehydro-2-methoxyca rbonyltropane (anhydroecgonine methyl ester) Er 1... 

Jacob, P., III, Lewis, E.R., Elias-Baker, B.A., and Jones, R., A pyrolysis product, anhydroecgonine methyl ester (methylecgonidine) is in the urine of cocaine smokers, J. Anal. Toxicol., 14, 353-357,1990. 

The metabolic scheme of cocaine analytes in hair. (Abbreviations COC, cocaine BE, benzoylecgonine EME, ecgonine methyl ester ECG, ecgonine CE, cocaethylene NCOC, norcocaine NCE, norcocaethylene and AEME, anhydroecgonine methyl ester). 

Cocaine served as an intermediate in the synthesis of the homotropane anatoxin-a (13b). Anhydroecgonine was converted into the methylketone (11), which was treated with trimethylsulphoxonium methylide the resultant endo cyclopropane (12b) was subsequently photolysed. Ring cleavage could also be... 

With the exception of ecgonine and anhydroecgonine, all of the bodies in the foregoing list are easily decomposable, splitting up when heated to from 80° to 100° C. with hydrochloric acid, or when boiled with alcoholic potassium hydroxide. 

An interesting new route to tropane derivatives, particularly to anhydroecgonine, has been outlined (122). Methylamine reacts with cycloheptatrienecarboxylic acid giving rise to ( )-anhydroecgonine, that is, trop-2-enecarboxylic acid. This reaction may be looked upon as a reversal of the elimination reaction that takes place with tropinone methiodide and its hydroxy and bromo derivatives (121). 

Tropane-2-carboxylates (21) have been synthesized by reaction of Grignard reagents with anhydroecgonine (21a) was claimed to be 16 times as active as cocaine in the locomotor activity test while (21b) was 64 times as active. Compound (21a) retained only 10—20% of the anaesthetic activity of cocaine. The fluoro-derivative (21b) proved 5—20 times as active as cocaine in the reserpine-induced ptosis prevention and reversal tests, respectively. 

The preparation of a number of 0-acyl derivatives of Z-ecgonine prove the presence of an alcoholic hydroxyl in this base. Furthermore, the original base may be dehydrated to anhydroecgonine, a product which is unsaturated towards permanganate and bromine. Dihydroanhydroecgonine... 

Avico U, Optical rotation of ecgonine and anhydroecgonine. Rend 1st Super. Sanita26,1024-30 (1963) CA 61 11361b. Cited in Perrin Bases Supplement 7472. NB Reported pK = 11.2 for ecgonine. For anhydroecgonine, reported pK = 9.8 and pK = 10.2. 

Davies has reported the synthesis of enantiomerically enriched tropanes 42 by the rhodium(II) octanaote catalyzed reaction of various N-Boc pyrroles 40 with vinyldiazomethanes 41 bearing chiral auxiliaries <97JOC1095, 97AA107>. This overall 3+4 annulation occurs by a tandem cyclopropanatlon/Cope rearrangement and was applied by the author to the synthesis of (-)-anhydroecgonine methyl ester and (-)-ferruginine. 

The synthetic utility of this chemistry was highlighted by short syntheses of various biologically interesting tropanes (Scheme 36). T vo natural products, ferruginine (98) and anhydroecgonine methyl ester (99), have been prepared by selectively hydrogenating the appropriate [3+4] aimulation product followed by ]V-deprotection and iV-methylation. A number of 4P-aryl-3p-propanoyl tropanes, such... 

Analysis of total cocaine residues in wastewater has been validated using LC-ESI-MS/MS [81]. After an alkaline hydrolysis step, the total cocaine was estimated by the amount of the degradation products ecgonine, anhydroecgonine, and norecgonine detected in the samples. 

Da Costa et al. [113] developed and validated a method for the simultaneous determination of cocaine, benzoylecgonine, cocaethylene, anhydroecgonine, anhydroecgonine methyl ester, and ecgonine methyl ester in human urine using CE-ESl-MS/MS. The electrolyte was 1 mol formic acid, whereas 0.05 mol formic acid in methanol to water (1 1) was used as the composition of the coaxial sheath liquid at the ESI nozzle. LODs were 100 ng mL for cocaine and cocaethylene and 250 ng mL for the other metabolites, whereas LOQs were... 

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