Strychnine compounds

Propylene glycol has been obtained from the optically inactive glycol by the action of bacteria,1 and by means of strychnine compounds.2 The present method is based on that of Farber, Nord and Neuberg.3... 

The dioxalato-dipyridino-iridium compounds cannot be resolved into optical isomers, although the cts-form of the compound, [IrCl2 (C204)2]K3, has been resolved through the strychnine compounds.2... 

Similar behavior can be observed even in the case of substituted quinuclideines 170). Neostrychnine (68) serves as an example of more complex compounds which show spectra differing from those of other enamines. The ultraviolet spectrum of this compound exhibits no batho-chromic shift and its basicity is considerably decreased 159,171,172) (pK in methylcellosolve at 20° is 3.8, whereas the analogous saturated compound has a pK under the same conditions of 7.45, and a compound with the double bond further removed, strychnine, has a pK of 7.37). As another example, the ultraviolet spectrum of trimethyl conkurchine (69) shows the same absorption maxima as a saturated tertiary amine (A in ether, about 213 m/i). 

Faolini and Divizia have succeeded in partially resolving inactive linalol into its optically active isomers hut only to the extent of optical rotations of + 1° 70 and — 1° 60 respectively. Linalol was converted into its acid phthalate, and an alcoholic solution of this compound was treated with the equivalent quantity of strychnine. By fractional crystallisation the laevo-rotatory salt, yielding dextro-rotatory linalol, separates first, leaving the more soluble dextro-rotatory strychnine salt, which yielded laevo-rotatory linalol in the mother liquor. 

A growing number of other diverse compounds have also been shown to bind to an allosteric site on the muscarinic receptors. Among them are pirenzepine (highly selective for Mi receptor), lidocaine and verapamil (ion channel blockers), tacrine (anticholinesterase compound), batrachotoxin, and strychnine (glycine receptor antagonist) [25,31-35],... 

New modifiers have traditionally been discovered by the trial-and-error method. Many naturally occurring chiral compounds (the chiral pool38) have been screened as possible modifiers. Thus, the hydrogenation product of the synthetic drug vinpocetine was discovered to be a moderately effective modifier of Pt and Pd for the enantioselective hydrogenation of ethyl pyruvate and isophorone.39 Likewise, ephedrine, emetine, strychnine, brucine, sparteine, various amino acids and hydroxy acids, have been identified as chiral modifiers of heterogeneous catalysts.38... 

As a part of a further investigation of the impact of 1,1-ADEQUATE data on CASE programs, Cheatham and co-workers46 employed retrorsine (22) and delcosine (23) as model compounds. HMBC and 1,1-ADEQUATE data were acquired for 22 and a suite of HMBC, H2BC, and 1,1-ADEQUATE spectra were acquired for 23. Usefully, the authors also reported details of their efforts to optimize the acquisition of the 1,1-ADEQUATE data used as input for the CASE investigation. Strychnine (1) was used by the authors to explore the optimization of experimental conditions. Using a 600-MHz instrument equipped with a 5-mm cryoprobe, the authors compared s/n for various 1,1-ADEQUATE correlations of strychnine using 10 mg samples in 5 mm tubes, and both 5 and 2.5 mg samples in 3 mm tubes. Acquisition times of 15 h were used for these measurements. 

Using strychnine (1) as a model compound, Martin et al.49 showed that subjecting a multiplicity-edited GHSQC spectrum and a 60-Hz optimized... 

Since the initial reports of HSQC-1,1-ADEQUATE spectra are very recent,49,50 there are only the reports by the author and co-workers in the literature. Aside from the initial work done using strychnine (1) as a model compound, applications to the complex antifungal agent posaco-nazole (47)96 and the cyclin-dependant kinase inhibitor dinaciclib (48)97 are the only other applications that have been reported. 

Paquin in 1948 found that a strongly exothermic reaction occurred when 40% formaldehyde was added to a solution of sulfamide in 25% aqueous ammonia. At once beautiful crystals precipitated they were recrystallized from 96% alcohol to give a compound, C5H10N4SO2, mp 224-225 "C, in 88% yield.245 From the similar character to hexamethylenetetramine, he named this product pentamethylenetetramine sulfone it is 225. One year later, in 1949, Hecht and Henecka at Bayer research laboratory reported that a condensation product from one mole of sulfamide in strong mineral acid and two moles of formaldehyde showed very strong toxicity and was five times more toxic than strychnine. They called this product (226) tetra-methylenedisulfotetramine. 246... 

Rh(C204)3 was resolved by Werner as the strychnine salt but other ions, such as Coen3+ and Niphen3+, have been used more regularly for this [84], The dinuclear rhodium(II) acetate is described in section 2.8.2 the dinuclear structure is retained on one-electron oxidation, but when ozone is used as the oxidant, a compound with a trinuclear Rh30 core is formed, analogous to those formed by Fe, Cr, Mn and Ru. (It can also be made directly from RhCl3.)... 

A novel procedure for the synthesis of an indole skeleton 81 was developed by Mori s group (Scheme 13).16e,16f Enantioselective allylic amination of 78 with A-sulfonated < r/ < -bromoaniline 79 followed by Heck cyclization of 80 provided chiral indoline 81. The treatment of a cyclohexenol derivative 78 with 79 in the presence of Pd2(dba)3-GHGl3 and ( )-BINAPO gave compound 80 with 84% ee in 75% yield. Total syntheses of (—)-tubifoline, (—)-dehydrotubifoline, and (—)-strychnine were achieved from compound 80. 

Many people believe that organic or natural psychedelics such as peyote, magic mushrooms and marijuana are safer or produce better trips than synthetic compounds. This is almost certainly false, since any plant material contains hundreds of compounds, many of which have a definite toxicity, but few of which have psychedelic properties (they tend to make you sick, not stoned). The various impurities or the additives (e.g., amphetamine, belladona, strychnine) sometimes found in synthetic preparations are probably no more toxic than many of the compounds found in the psychedelic plants, and like these compounds, such additives or impurities probably have relatively little effect on the trip. 

Using strychnine (1) as a model compound, a pair of HSQC spectra are shown in Fig. 10.16. The top panel shows the HSQC spectrum of strychnine without multiplicity editing. All resonances have positive phase. The pulse sequence used is that shown in Fig. 10.15 with the pulse sequence operator enclosed in the box eliminated. In contrast, the multiplicity-edited variant of the experiment is shown in the bottom panel. The pulse sequence operator is comprised of a pair of 180° pulses simultaneously applied to both H and 13C. These pulses are flanked by the delays, A = l/2(xJcii), which invert the magnetization for the methylene signals (red contours in Fig. 10.16B), while leaving methine and methyl resonances (positive phase, black contours) unaffected. Other less commonly used direct heteronuclear shift correlation experiments have been described in the literature [47]. 

Potential Uses of These Polymers. We have studied the phenyl isocyanate modification of poly(vinyl alcohol) as a model system. Many uses exist for carbamates as medicines, pesticides and herbicides (67,68). For example, ethyl carbamate has been used to treat leukemia and multiple myeloma. Ethyl carbamate has also been used as an antidote for central nervous system poisoning by strychnine. The tranquilizer Meprobamate is a carbamate derivitive. Numerous pesticides and herbicides, such as Sevin and Propham, are also carbamate derivatives. Propham is isopropyl N-phenylcarbamate which bears a strong resemblence to the polymers of Equation 21, and this compound is used as a preemergence herbicide. Numerous other close analogs could be cited also. We might note also that the N-phenyl carbamoyl unit bears... 

More recent examples of biomimetic synthesis are the syntheses of thebaine [11] and usnic acid [12], as well as strychnine [13], morphine alkaloids [11] [14] and a great number of terpenic compounds [15]. On the other hand, hypothetic prebiotic considerations may also simplify tremendously the synthetic plans. Such is the case, for example, of the work of Eschenmoser on vitamin B12 who, after synthesising it in collaboration with Woodward by a linear sequence of almost fifty steps [16], investigated the prebiotic origen of this complex molecule. The experimental work undertaken in this direction demonstrates that the amount of "external instruction" required for "self-assembling" the different structural elements present in this molecule is surprisingly small. This fact could eventually lead to a very simple synthesis of vitamin Bj2 starting from a-amino nitriles which would involve only a few steps [17]. 

One of the most known toxic alkaloid is strychnine. Vanderkop" and Sterner et aU are examples of those who have studied its toxicity, although it is practically rather evident. This alkaloid has been used as a strong rodenticide. It is also known for being dangerous to humans. One general characteristic of strychnine is its chemical stability. This is some kind of exception in the alkaloids, which are generally flexible heterogeneous compounds. In cases of... 

At the turn of the nineteenth century, methods became available for the isolation of active principles from crude drugs. The development of chemistry made it possible to isolate and synthesize chemically pure compounds that would give reproducible biological results. In 1806, Serturner (1783-1841) isolated the first pure active principle when he purified morphine from the opium poppy. Many other chemically pure active compounds were soon obtained from crude drug preparations, including emetine by Pelletier (1788-1844) from ipecacuanha root quinine by Carentou (1795-1877) from cinchona bark strychnine by Magendie (1783-1855) from nux vomica and, in 1856, cocaine by Wohler (1800-1882) from coca. 

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