On the neuropharmacology of Harmane and other β-carbolines

Müller, Wernér E.G.; Fehske, Klaus J.; Borbe, Harald O.; Wollert, U.; Nanz, Christel; Rommelspacher, Hans

doi:10.1016/0091-3057(81)90133-7

Cited by 110 publications

(30 citation statements)

References 24 publications

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“…(4) have demonstrated with in vitro testing that harmane and similar drugs interact with a number of neurotransmitter systems in addition to the benzodiazepine 1,2,3,4-tetrahydroharniane (hereaftzr THHCA, 2) was undertaken to obtain topochemical information on the precursor of the ester derivatives found in vivo. Conformational analysis via ''C nmr of other 1,3-disubstituted unsaturated P-carbolines ( 5 ) predicted that for this compound the cis diastereonier with the 1,3 hydrogen atoms in axial positions would predominate.…”

Section: Introductionmentioning

confidence: 99%

Structure–activity studies of β-carbolines. 1. Molecular structure and conformation of cis-3-carboxylic acid-1,2,3,4-tetrahydroharmane dihydrate

Codding¹

1983

Can. J. Chem.

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The crystal structure of cis-3-carboxylic acid-1,2,3,4-tetrahydroharmane dihydrate, C13H13N2O2•2H2O, a putative ligand of the benzodiazepine receptor is reported. The space group is P21/c with a = 14.850(4), b = 6.560(3), c = 14.746(4) Å and β = 117.411(8)°, Z = 4. The molecule crystallizes as a zwitterion with the unsaturated ring in a half-chair conformation. Hydrogen bonding to the water molecules included in the lattice determines the molecular packing arrangement.

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Section: Introductionmentioning

confidence: 99%

Structure–activity studies of β-carbolines. 1. Molecular structure and conformation of cis-3-carboxylic acid-1,2,3,4-tetrahydroharmane dihydrate

Codding¹

1983

Can. J. Chem.

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“…on cyclic guanosine monophosphate [20] and on cerebral glu cose consumption [21]. Other authors [22,23] suggest that harmine activity may be -at least in part -the result of its interaction with ben zodiazepine-specific recognition sites. This activity, however, cannot explain the effects on L-Dopa AUC and on the modifications of DA brain levels reported here.…”

Section: Discussionmentioning

confidence: 99%

Different Effects of Harmine on Plasma Concentrations of L-Dopa and on Cerebral Dopamine Metabolism in Rabbits and Rats

1994

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The effects of short-term intravenous administration of harmine, a monoamine oxidase inhibitor, on the plasma concentrations of L-Dopa and on dopamine levels in the brain striata of rats and rabbits after L-Dopa administration were studied. Harmine affects the L-Dopa plasma concentrations in rabbits but not in rats: in fact in the former species the area under the concentration-time curve observed after administration of L-Dopa alone increased significantly when animals were pre-treated with harmine. Dopamine striatal levels increased in concert with plasma L-Dopa concentrations after administration of L-Dopa in rats and rabbits. However pretreatment with harmine resulted in a significant increase of dopamine levels in the brain striata of rabbits only. These results suggest that harmine or one of its metabolites affect the brain dopamine system not merely as a type A monoamine oxidase inhibitor but with a modulatory effect, without a precise indication of site or mode of action of harmine.

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“…They are present in many plant families [2], human urine [3], human lenses [4] and cigarette and tobacco smoke [5]. They are known to be hallucinogens [6], to inhibit the monoamine oxidase (MAO) [7,8] and to have photosensitizing activity towards a variety of systems, including bacteria, fungi, viruses and insects [9,10]. They have been reported to produce singlet oxygen and super oxide radical anion with varying efficiency [11] and to yield under uv irradiation symmetric and asymmetric β-carboline dimers [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and isolation of nitro‐bT‐carbolines obtained by nitration of commercial β‐carboline alkaloids

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Erra‐Balsells

2001

Journal of Heterocyclic Chem

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Nitration of commercial full aromatic β-carboline alkaloids nor-harmane (1), harmane (2), harmine (3), harmol (4), and the 7-acetylated derivative of harmol (5) is described. Advantages and disadvantages of different nitration reagents which involve acidic conditions (HNO 3 /H + ) and neutral conditions (Cu(NO 3 ) 2 ; ceric ammonium nitrate) are discussed. A complete 1 H and 13 C-nmr characterization including ms and also uv absorption spectra in neutral and acid media is presented. A detailed ei-ms and ld-tof-ms study is enclosed because the nitro-β-carbolines constitute a new family of β-carboline-like chromophores with potential use as matrix in uv-maldi-tof-ms.

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On the neuropharmacology of Harmane and other β-carbolines

Cited by 110 publications

References 24 publications

Structure–activity studies of β-carbolines. 1. Molecular structure and conformation of cis-3-carboxylic acid-1,2,3,4-tetrahydroharmane dihydrate

Structure–activity studies of β-carbolines. 1. Molecular structure and conformation of cis-3-carboxylic acid-1,2,3,4-tetrahydroharmane dihydrate

Different Effects of Harmine on Plasma Concentrations of L-Dopa and on Cerebral Dopamine Metabolism in Rabbits and Rats

Synthesis and isolation of nitro‐bT‐carbolines obtained by nitration of commercial β‐carboline alkaloids

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