Profenamine

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Walter Schunack - One of the best experts on this subject based on the ideXlab platform.

  • Zur Synthese von (Z)- und (E)-3-(1H-imidazol-4-yl)-2-propenamin und einigen 3-(1H-Imidazol-4-yl)propanaminen
    European Journal of Organic Chemistry, 1992
    Co-Authors: Christian Sellier, Armin Buschauer, Walter Schunack
    Abstract:

    Synthesis of (Z)- and (E)-3-(1H-imidazol-4-yl)-2-propenamine and Some 3-(1H-imidazol-4-yl)propanamines 3-(1H-Imidazol-4-yl)propanamine (6, homohistamine), an essential intermediate for the synthesis of potent impromidine-type histamine H2 receptor agonists, is efficiently prepared from trans-urocanic acid (1) by reduction of the methyl ester 2 and conversion to the saturated amide 4. Dehydration with thionyl chloride yields the nitrile 5 which is subsequently reduced to 6. Side-chain methylated 3-(1H-imidazol-4-yl)propanamines 12 are available from 1H-imidazole-4-carbaldehyde (7) and 1-(1H-imidazol-4-yl)ethanone (8), respectively, via unsaturated nitriles 10 and stepwise reduction. Cyclization of the appropriate 4-bromo-5-oxohexanenitriles 14α with formamidine in liquid ammonia and reduction of the obtained nitriles 15 furnishes ring-methylated amines 16. (E)-3-(1H-Imidazol-4-yl)-2-propenamine [(E)-23] is obtained in six steps from the trans-ester 2 while (Z)-23 is accessible by treating 7 with triphenyl(2-phthalimidoethyl)phosphonium bromide (17) and final deprotection. These primary amines are valuable intermediates for the synthesis of impromidine analogues.

Christian Sellier - One of the best experts on this subject based on the ideXlab platform.

  • Zur Synthese von (Z)- und (E)-3-(1H-imidazol-4-yl)-2-propenamin und einigen 3-(1H-Imidazol-4-yl)propanaminen
    European Journal of Organic Chemistry, 1992
    Co-Authors: Christian Sellier, Armin Buschauer, Walter Schunack
    Abstract:

    Synthesis of (Z)- and (E)-3-(1H-imidazol-4-yl)-2-propenamine and Some 3-(1H-imidazol-4-yl)propanamines 3-(1H-Imidazol-4-yl)propanamine (6, homohistamine), an essential intermediate for the synthesis of potent impromidine-type histamine H2 receptor agonists, is efficiently prepared from trans-urocanic acid (1) by reduction of the methyl ester 2 and conversion to the saturated amide 4. Dehydration with thionyl chloride yields the nitrile 5 which is subsequently reduced to 6. Side-chain methylated 3-(1H-imidazol-4-yl)propanamines 12 are available from 1H-imidazole-4-carbaldehyde (7) and 1-(1H-imidazol-4-yl)ethanone (8), respectively, via unsaturated nitriles 10 and stepwise reduction. Cyclization of the appropriate 4-bromo-5-oxohexanenitriles 14α with formamidine in liquid ammonia and reduction of the obtained nitriles 15 furnishes ring-methylated amines 16. (E)-3-(1H-Imidazol-4-yl)-2-propenamine [(E)-23] is obtained in six steps from the trans-ester 2 while (Z)-23 is accessible by treating 7 with triphenyl(2-phthalimidoethyl)phosphonium bromide (17) and final deprotection. These primary amines are valuable intermediates for the synthesis of impromidine analogues.

Katsuya Honda - One of the best experts on this subject based on the ideXlab platform.

  • simple and simultaneous determination for 12 phenothiazines in human serum by reversed phase high performance liquid chromatography
    Journal of Chromatography B, 2007
    Co-Authors: Einosuke Tanaka, Takako Nakamura, Masaru Terada, Tatsuo Shinozuka, Chikako Hashimoto, Katsuyoshi Kurihara, Katsuya Honda
    Abstract:

    A high-performance liquid chromatographic method has been developed for the simultaneous analysis of the 12 phenothiazines (chlorpromazine, fluphenazine, levomepromazine, perazine, perphenazine, prochlorperazine, Profenamine, promethazine, propericiazine, thioproperazine, thioridazine and trifluoperazine) in human serum using HPLC/UV. The separation was achieved using a C 18 reversed-phase column (250 mm x 4.6 mm I.D., particle size 5 μm, Inersil ODS-SP). The mobile phase, consisting of acetonitrile-methanol-30 mM NaH 2 PΟ 4 (pH 5.6) (300:200:500, v/v/v), was delivered at a flow rate of 0.9 mL/min and UV detection was carried out at 250 nm. The recoveries of the 12 phenothiazines spiked into serum samples were 87.6-99.8%. Regression equations for the 12 phenothiazines showed excellent linearity, with detection limits of 3.2-5.5 ng/mL for serum. The inter-day and intra-day coefficients of variation for serum samples were commonly below 8.8%. The selectivity, accuracy and precision of this method are satisfactory for clinical and forensic purposes. This sensitive and selective method offers the opportunity for simultaneous screening and quantification of almost all phenothiazines available in Japan for the purposes of clinical and forensic applications.

Armin Buschauer - One of the best experts on this subject based on the ideXlab platform.

  • Zur Synthese von (Z)- und (E)-3-(1H-imidazol-4-yl)-2-propenamin und einigen 3-(1H-Imidazol-4-yl)propanaminen
    European Journal of Organic Chemistry, 1992
    Co-Authors: Christian Sellier, Armin Buschauer, Walter Schunack
    Abstract:

    Synthesis of (Z)- and (E)-3-(1H-imidazol-4-yl)-2-propenamine and Some 3-(1H-imidazol-4-yl)propanamines 3-(1H-Imidazol-4-yl)propanamine (6, homohistamine), an essential intermediate for the synthesis of potent impromidine-type histamine H2 receptor agonists, is efficiently prepared from trans-urocanic acid (1) by reduction of the methyl ester 2 and conversion to the saturated amide 4. Dehydration with thionyl chloride yields the nitrile 5 which is subsequently reduced to 6. Side-chain methylated 3-(1H-imidazol-4-yl)propanamines 12 are available from 1H-imidazole-4-carbaldehyde (7) and 1-(1H-imidazol-4-yl)ethanone (8), respectively, via unsaturated nitriles 10 and stepwise reduction. Cyclization of the appropriate 4-bromo-5-oxohexanenitriles 14α with formamidine in liquid ammonia and reduction of the obtained nitriles 15 furnishes ring-methylated amines 16. (E)-3-(1H-Imidazol-4-yl)-2-propenamine [(E)-23] is obtained in six steps from the trans-ester 2 while (Z)-23 is accessible by treating 7 with triphenyl(2-phthalimidoethyl)phosphonium bromide (17) and final deprotection. These primary amines are valuable intermediates for the synthesis of impromidine analogues.

Einosuke Tanaka - One of the best experts on this subject based on the ideXlab platform.

  • simple and simultaneous determination for 12 phenothiazines in human serum by reversed phase high performance liquid chromatography
    Journal of Chromatography B, 2007
    Co-Authors: Einosuke Tanaka, Takako Nakamura, Masaru Terada, Tatsuo Shinozuka, Chikako Hashimoto, Katsuyoshi Kurihara, Katsuya Honda
    Abstract:

    A high-performance liquid chromatographic method has been developed for the simultaneous analysis of the 12 phenothiazines (chlorpromazine, fluphenazine, levomepromazine, perazine, perphenazine, prochlorperazine, Profenamine, promethazine, propericiazine, thioproperazine, thioridazine and trifluoperazine) in human serum using HPLC/UV. The separation was achieved using a C 18 reversed-phase column (250 mm x 4.6 mm I.D., particle size 5 μm, Inersil ODS-SP). The mobile phase, consisting of acetonitrile-methanol-30 mM NaH 2 PΟ 4 (pH 5.6) (300:200:500, v/v/v), was delivered at a flow rate of 0.9 mL/min and UV detection was carried out at 250 nm. The recoveries of the 12 phenothiazines spiked into serum samples were 87.6-99.8%. Regression equations for the 12 phenothiazines showed excellent linearity, with detection limits of 3.2-5.5 ng/mL for serum. The inter-day and intra-day coefficients of variation for serum samples were commonly below 8.8%. The selectivity, accuracy and precision of this method are satisfactory for clinical and forensic purposes. This sensitive and selective method offers the opportunity for simultaneous screening and quantification of almost all phenothiazines available in Japan for the purposes of clinical and forensic applications.