Ethanol induces an increase of harman in the brain and urine of rats

Rommelspacher, Hans; Damm, Henning; Strauss, Sabine; Schmidt, G.

doi:10.1007/bf00500903

Cited by 60 publications

(13 citation statements)

References 17 publications

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“…It is somewhat surprising that the fully aromatic compounds are probably more important than the tetrahydro compounds (25, 32,64). It remains to be elucidated whether the biosynthesis and/or the degradation of $C's are disturbed in alcoholics.…”

Section: Biologicalfunctionsmentioning

confidence: 97%

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β-Carbolines and Tetrahydroisoquinolines: Detection and Function in Mammals

Rommelspacher

May²,

Susilo³

1991

Planta Med

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108

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beta-Carbolines occur in man and rat. The concentration in various tissues is about 100 to 1000 times lower than that of classical neurotransmitters. Administration of beta-carbolines in animals induces overlapping but not identical activity profiles. The molecular modes of action differ. For example, harman (1-methyl-beta-carboline) acts as an endogenous inhibitor of monoamine oxidase [E.C. 1.4.3.4.], subtype A, whereas norharman (beta-carboline) probably acts by stimulation of a specific beta-carboline receptor which is different from the benzodiazepine-GABA receptor complex. There is substantial evidence that tetrahydroisoquinolines occur under physiological conditions as well. Whether tetrahydropapaveroline serves as a precursor of morphinanes in mammals, as has been found in opium poppies, remains to be elucidated.

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Section: Biologicalfunctionsmentioning

confidence: 97%

“…The fully aromatic fiG's have been assayed by HPLC with fluorometric detection (8). Harman was found in blood plasma and erythrocytes from non-alcoholic subjects (8), in human platelets (29a, 30), in rat lung (31), brain (31,32), rat and human urine (32, 33) as well as in 1 sample out of 24 of human cerebrospinal fluid (31).…”

mentioning

confidence: 99%

β-Carbolines and Tetrahydroisoquinolines: Detection and Function in Mammals

Rommelspacher

May²,

Susilo³

1991

Planta Med

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108

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“…Alcohol metabolism may lead to the formation of a beta-carboline compound called harman (33,34), and alcoholic beverages frequently contain harman (35), which has moderate affinity for MAO-A. To avoid temporary occupancy effects of harman (10), [ 11 C]-harmine PET scanning was timed at a point when harman levels were negligible (36), which was verified by plasma sampling.…”

Section: Protocol On Day Of Pet Imagingmentioning

confidence: 99%

Greater Monoamine Oxidase A Binding in Alcohol Dependence

Matthews

Kish

et al. 2014

Biological Psychiatry

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Background-Alcohol dependence (AD) is a multiorgan disease in which excessive oxidative stress and apoptosis are implicated. Monoamine oxidase A (MAO-A) is an important enzyme on the outer mitochondrial membrane that participates in the cellular response to oxidative stress and mitochondrial toxicity. It is unknown whether MAO-A levels are abnormal in AD. We hypothesized that MAO-A V T , an index of MAO-A level, is elevated in the prefrontal cortex (PFC) during AD, because markers of greater oxidative stress and apoptosis are reported in the brain in AD and a microarray analysis reported greater MAO-A messenger RNA in the PFC of rodents exposed to alcohol vapor.

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“…Harmane alkaloids have been detected in food plants [2] such as soy, rye, wheat, rice, barley, mushrooms, grape juice, wine [6], charred insects, and cigarette smoke. It has been reported that alcohol increases the harmane content in the brain and urine [7].Cytotoxic effects of harmane alkaloids have also been found [8]. These alkaloids are reported to affect the cardiovascular system [9, 10] and to have a hypotensive effect [10].…”

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confidence: 98%

mentioning

confidence: 99%

Diastereotopic synthesis of 1- and 1,1-substituted 4-phenyl-2,3,4,9-tetrahydro-1H-β-carbolines

Семенов¹,

Novikov²,

Spitsin³

et al. 2004

Chem Nat Compd

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547.759.3 V. N. Azev, 2 and V. V. Kachala 3A diastereotopic Pictet-Spengler reaction was performed to form previously unknown 1-and 1,1-substituted 4-phenyl-β-carbolines based on β-phenyltryptamine, aldehydes of various structure, and isatins. It has been demonstrated that the predominant diastereomers of the prepared β-carbolines have the (R*,R*) configuration. The diasteroselectivity (de) of the reaction varies from 44 to 88%.The Pictet-Spengler reaction, which occurs in plants and in humans, leads to the formation of various derivatives including isoquinoline and β-carboline.Some very simple alkaloids containing the β-carboline structural moiety and belonging to the harmane group are found in medicinal plants such as Passiflora fluidum [1], P. edulis, P. incarnata, Bansteriopsis caapi [2], and Peganum harmala [3], Zygophylaceae. They are used in traditional medicine to treat asthma, jaundice, and other diseases [3,4]. Harmaline is a known MAO inhibitor and powerful serotonin antagonist [5]. Harmane alkaloids have been detected in food plants [2] such as soy, rye, wheat, rice, barley, mushrooms, grape juice, wine [6], charred insects, and cigarette smoke. It has been reported that alcohol increases the harmane content in the brain and urine [7].Cytotoxic effects of harmane alkaloids have also been found [8]. These alkaloids are reported to affect the cardiovascular system [9, 10] and to have a hypotensive effect [10].The harmane alkaloids include also eleagnine [(1R)-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline]. A synthesis of the racemate of eleagnine (1a) using the Pictet-Spengler reaction based on tryptamine (1) and acetaldehyde was previously proposed [11].Much later eleagnine was biosynthesized [12] and synthesized enantioselectively [13,14] and (1S)-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline was synthesized enantioselectively (ee > 98%) [15]. The reaction proceeded through the formation of two diastereomers with subsequent fractional crystallization of one of them and removal of a sulfamide, which was known to be chiral.Recently the solid-phase chemistry of indole is rapidly developing with the Pictet-Spengler reaction being carried out on a polymeric support to synthesize 1,3-disubstituted β-carbolines. Diastereoselectivities (de) of 8-52% have been obtained from tryptophan [16][17][18][19][20][21][22][23][24][25]. It depended on the presence of a substituted nitrogen in the indole ring [20].Based on this, we carried out diastereotopic syntheses of previously unknown 4-phenyl-1-and 1,1-substituted β-carboline derivatives using the Pictet-Spengler reaction. The starting materials were β-phenyltryptamine (1) as the racemate and aliphatic, aromatic, and heterocyclic aldehydes.

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Ethanol induces an increase of harman in the brain and urine of rats

Cited by 60 publications

References 17 publications

β-Carbolines and Tetrahydroisoquinolines: Detection and Function in Mammals

β-Carbolines and Tetrahydroisoquinolines: Detection and Function in Mammals

Greater Monoamine Oxidase A Binding in Alcohol Dependence

Diastereotopic synthesis of 1- and 1,1-substituted 4-phenyl-2,3,4,9-tetrahydro-1H-β-carbolines

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