Bruce A. Lodge

Aromatic Iodination with Iodine and Silver Sulfate

Abstract Iodination of alkyl and alkoxybenzenes with iodine and silver sulfate at room temperature gives iodinated aryl compounds in good yield.

Iodination of alkylbenzenes with iodine and silver nitrite

Abstract Iodination of alkylbenzenes with iodine and silver nitrite at room temperature gives iodoalkylbenzenes in good yield.

Analysis of estrogen sulphate mixtures in pharmaceutical formulations by reversed-phase chromatography

The relative retention times of estrogen sulphates for reversed-phase, ion-pair and argentous chromatography have been determined. Detector wavelengths of 200 nm, 200 nm and 270 nm were used, respectively. Samples are prepared by dissolution of pharmaceutical formulations in the high-performance liquid chromatography (HPLC) eluent. With reversed-phase chromatography, the estrone, equilin and 17 alpha-dihydroequilin estrogen sulphates are resolved from other estrogen sulphates in 20 min. Any traces of free estrogens which might be present are eluted too slowly for the formation of chromatographic peaks. With ion-pair chromatography, any hydrolyzed estrogens would be eluted before the sulphates with the formation of resolved chromatographic peaks. With argentous chromatography the retention times of the estrogen sulphates varied by nearly a factor of four. The utility of HPLC for the analysis of estrogen sulphates in pharmaceuticals is discussed.

Synthesis and Spectral Properties of 2,5-Dimethoxy-4-Ethoxyamphetamine and Its Precursors

2,5-Dimethoxy-4-ethoxyamphetamine (MEM) was synthesized by two routes. The gas liquid chromatographic data and ultraviolet, infrared, proton magnetic resonance, carbon-13 magnetic resonance, and mass spectra are presented for this amphetamine as well as its precursors. This amphetamine was found to be identical to the sample submitted by the police.

New street analogs of phencyclidine

Abstract In the Summer of 1989 two new street analogs of phencyclidine (PCP) appeared in Canada. Analysis showed these to possess a benzyl and 4-methylphenyl moiety, respectively in place of the phenyl group of PCP itself. For the sake of completeness, we have synthesized the 2-methylphenyl and 3-methylphenyl isomers, also in the expectation that these compounds themselves may at some point appear on the illicit market. The UV, IR, 1 H-NMR, 13 C-NMR and GC MS spectra are published here.

The reinforcing and discriminative stimulus properties of para-ethoxy- and para-methoxyamphetamine

The purpose of this study was two-fold: 1) to assess the degree to which para-methoxyamphetamine and para-ethoxyamphetamine maintain self-administration behavior, and 2) to determine the similarity or difference between these drugs and amphetamine in drug discrimination tests. Animals were trained to self-administer 0.3 mg/kg/infusion cocaine on a fixed-ratio 5 (FR5) schedule of reinforcement. Substitution of para-ethoxyamphetamine (PEA), para-methoxyamphetamine (PMA), or saline produced similar results; in all cases responding decreased substantially. A separate group of animals was trained to discriminate amphetamine (1 mg/kg) from saline in a fixed-ratio (FR10), food-reinforced paradigm. PEA and PMA produced only limited responding on the amphetamine-appropriate lever (maximum of approximately 30%). Both PMA and PEA had effects on response rate which were similar to those of amphetamine, although PMA had slightly greater rate-decreasing effects than the other two compounds. These data suggest that neither PMA nor PEA are reinforcing in rats, and do not possess amphetamine-like discriminative properties.

The synthesis and spectra of 4-ethoxyamphetamine and its isomers

Abstract The appearance on the street of 4-ethoxyamphetamine (4-EA) led to the need for a reference standard to be synthesized. To satisfy concerns that this compound could be distinguished from the isomeric 2- and 3-ethoxyamphetamines (2-EA and 3-EA, respectively), standards for each of those substances were also synthesized, in each case as the hydrochloride salt. The UV, IR, 1 H-NMR, 13 C-NMR and GC/mass spectra are reported here for all three amphetamines.

CHEMICAL AND PHYSICAL PROPERTIES OF (Z)—AND (E) -MONOETHOXY-1-(2-NITRO-1-PROPENYL) BENZENES: Important Precursors to the monoethoxyamphetamines

ABSTRACT(Z)-Monoethoxy-1- (2-nitro-1-propenyl)benzenes were synthesized from the corresponding (E)-isomers by irradiation with light in toluene in the presence of benzophenone. The gas-liquid chromatographic (GLC) and thin-layer chromatographic (TLC) data, and ultraviolet (UV), infrared (IR), proton magnetic resonance (1H-NMR), and mass spectra (MS) are presented for both isomers for comparison. The (Z)-isomer is partially converted on the injector of GLC apparatus to the (E)-isomer.

Characterization of Cis-Cinnamoylcocaine

ABSTRACTThe physical properties of highly purified cis-cinnamoylcocaine are reported, including the proton and carbon NMR, IR, UV and mass spectra; the melting point is 72–73°. Details of the chromatographic purification are also given.

Discriminative stimulus properties of substituted amphetamine derivatives

Animals were trained to discriminate amphetamine (1 mg/kg) from saline in a fixed-ratio (FR 10), food-reinforced paradigm. Amphetamine-appropriate responding was engendered by the training dose, and by 3 mg/kg, while at lower doses there was a progressive decrease in the extent of responding on the drug-appropriate lever. The following three novel amphetamine derivatives were tested for their ability to produce amphetamine-appropriate responding: 2,5-dimethoxy-4-ethoxy-amphetamine (DMEA); 2,5-dimethoxy-4-methylthio-amphetamine (DMMTA), and 2,4,5-trimethoxy-amphetamine (TMA). DMEA produced only minimal (< 20%) amphetamine-appropriate responding over a dose range of 0.1-10 mg/kg. Substantial decreases in response rate limited testing of the other amphetamines to a dose maximum of 3 mg/kg, but over the range of 0.1-3.0 mg/kg there was little evidence for generalization. At 3 mg/kg of either DMMTA or TMA, only 2 of 10 animals completed at least one uninterrupted FR 10 on either lever, and with either compound only 1 of these 2 animals responded more than 50% on the drug-appropriate lever. Of the three compounds tested, DMMTA had the greatest response rate-decreasing effect.