Harmaline, determination

Recently the continuous-addition-of-reagent (CAR) technique [182] was applied for the determination of fluorophores by POCL chemistry [95-99], The applicability of this technique was demonstrated by the determination of natively fluorescent acepromazine in horse plasma [95], the alkaloid harmaline in plasma [96], and other dansylated alkaloids [97], A separation step has also been included and applied to postcolumn detection of PAHs [98] and dansylated P-carboline alkaloids [99],... 

P-Carboline alkaloids (harmaline, har-malol, harmane, harmol, harmine) 0.3-150 0.25-90 2.9-3.1 Harmaline was determined in plasma samples DNPO was used as aryl oxalate 45... 

Moncrieff J. (1989). Determination of pharmacological levels of harmane, harmine, and harmaline in mammalian brain tissue, cerebrospinal fluid, and plasma by high-performance liquid chromatography with fluorimetric detection. J Chromatogr. 496(2) 269-78. 

SYNTHESIS A stirred solution of 1.0 g harmaline hydrochloride in 25 mL H2O was covered with a pad of Argon, and there was added 0.1 g Pt02 followed by the dropwise addition of 0.4 g NaBH4 in 4.0 mL H2O over the course of 20 min. The pH was determined periodically and the reaction mixture was kept acidic during this... 

Hochstein and Paradies determined in 1957 that results from ingestion of yagi (without other botanical additives) came mainly from interaction of three molecules—harmaline, harmine and -1,2,3,4-tetrahydroharmine. These findings have been accepted since then by investigators of this plant family. 

The ionization constants of the first excited states of p-carboline and three of its derivatives - harmane. harmine, and 2-methylharmine - have been re-ported, and the fluorescence and phosphorescence spectra of harmine, harmaline, and 3-dehydroreserpines have been determined in neutral, acidic, and basic solution at 298 and 77 K. The photo-oxidation of 3-dehydroreserpines has also been examined in this work. The luminescence spectra of a series of indole alkaloids have also been reported by the same workers. The effect of pH on the absorption and fluorescence spectra of sanquinonine, a benzophenanthridine alkaloid, have been studied in detail. 

As a graduate student at Manchester, Manske determined the structures of harmine and harmaline and synthesized both alkaloids. He also synthesized rutaecarpine, as he liked to recall, by accident. Another fortuitous experiment was his discovery of the use of hydrazine in the hydrolysis of phthalimides. He also collaborated at this time with A. Lapworth in one of the pioneering studies of physical organic chemistry. He was awarded the Ph.D. by Manchester in 1926. 

Non-isoprenoid Tryptamines. The stems of Picrasma ailanthoides, from which plant canthine derivatives had previously been obtained, has now yielded 1-methoxycarbonyl- and l-hydroxymethyl-j5-carboline. The molecular shape of eserine (= physostigmine) in the crystal has been determined. The new evidence fits in well with information, summarized previously, from n.m.r. NOE measurements. More alkylations at the C-1 methyl of harmaline have been reported.The A -methyl derivative of 1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine has been isolated from cranberries. 

Tubulosine, C29H37O3N3 (mp 261° [a]p -66°) monoacetyl (mp 186°) diacetyl (mp 151°) is a remarkable example of an alkaloid which is partly emetine and partly harmaline. Its structural determination is also an example of the powerful tools of spectral analyses in this case mass spectra for the greater part. The only chemical manipulation which gave structural information was the permanganate oxidation of the alkaloid to m-hemipinic acid. 

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