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Alpha Methylbenzylamine

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F.f. Knapp – One of the best experts on this subject based on the ideXlab platform.

  • Effects of configuration on the myocardial uptake of radioiodinated 3(R)-BMIPP and 3(S)-BMIPP in rats.
    Journal of nuclear medicine : official publication Society of Nuclear Medicine, 1997
    Co-Authors: Qun Lin, F. Mokler, K.r. Ambrose, A.l. Beets, H. Luo, D.w. Mcpherson, Joachim Kropp, F.f. Knapp
    Abstract:

    UNLABELLED Radioiodinated 3(R)-(+)- and 3(S)-(-)-15-(p-iodophenyl)-3-(R,S)-methylpentadecanoic acid (BMIPP) were prepared and evaluated in rats to investigate the effects of absolute configuration of the 3(beta)-methyl group on myocardial uptake and release kinetics. METHODS The 3(R)-(+)-BMIPP analog was synthesized by initial acylation of a thiophene template with the acid chloride of ethyl 3(R)-methylglutarate. 3(S)-(-)-BMIPP was obtained by separation from the mixture of diastereomeric amides prepared from reaction of the acid chloride of racemic BMIPP with the S-(-)-AlphaMethylbenzylamine. The amide of synthetic 3(R)-BMIPP prepared from S-(-)-AlphaMethylbenzylamine was identical to the chromatographically more polar isomer. Free acids were obtained by acid hydrolysis of the amides, fully characterized and then converted to the radioiodinated BMIPP isomers. RESULTS Biodistribution studies in rats with the dual-labeled [(131)I]-3(S)-BMIPP/[(125)I]-3(R)-BMIPP mixture demonstrated greater myocardial uptake of 3(R)-BMIPP compared with the 3(S)-BMIPP isomer [60 min: 3(R)-BMIPP = 4.37 %ID/g; 3(S)-BMIPP = 3.44; p < 0.05; 180 min, 2.31 and 1.78 %ID/G, respectively, p < 0.01], although both isomers had similar myocardial washout curves (5-180 min). Percent ID/g values for other tissues which were examined (blood, lungs, thyroid) were similar. CONCLUSION Higher myocardial uptake of the 3(R)-BMIPP isomer observed in these animal studies may suggest differences in carrier-mediated myocyte uptake of the two isomers. These studies suggest that [(123)I]-3(R)-BMIPP is a candidate for clinical evaluation and may show greater myocardial uptake than the 3(S)-BMIPP isomer and may thus require reduced injected dose.

  • Nuclear medicine program progress report for quarter ending December 31, 1995
    , 1995
    Co-Authors: F.f. Knapp, K.r. Ambrose, A.l. Beets, H. Luo, D.w. Mcpherson, S. Mirzadeh, F. Mokler
    Abstract:

    In this report we describe the first resolution of the 3R-(+)-and 3S- ({minus})-methyl BMIPP methyl-branched fatty acid stereoisomers and biodistribution of the radioiodinated isomers in rats to investigate the effects of the configuration of the 3({beta})-methyl group on the organ distribution and myocardial uptake and release kinetics. Synthesesis of 3R-(+)BMIPP was accompanied by initial acylation of the thiophene template with the acid chloride of ethyl 3R- methylglutarate. The amide of the synthetic 3R-BMIPP isomer prepared S-(-)-{Alpha}-Methylbenzylamine exhibited identical spectral and chromatographic properties with the chromatographically more polar isomer (TLC and HPLC) which was separated from the mixture of amides prepared from reaction of the acid chloride of racemic BMIPP with the S-(-)-{Alpha}-Methylbenzylamine. The second less chromatographically polar amide isomer was assigned the 3S-(-)-methyl configuration. The free acids were obtained by acid hydrolysis of the amides and converted to the radioiodinated analogues. While biodistribution studies in separate groups of rats demonstrated greater myocardial uptake of 3R-BMIPP compared with the 3S-isomer values for most other tissues evaluated (blood, lungs, kidneys and thyroid) were similar, whereas the 3S-BMIPP isomer consistently showed higher liver uptake. These results were confirmed in a [l-131]-3S-BMIPP/[l-125]-3R-BMIPP dual label study and both isomers had similar myocardial wash-out curves (5-180 min). These studies suggest that [l-123]-3R-BMIPP is a candidate for clinical evaluation and may show greater myocardial uptake than the 3S-isomer and thus may require a reduced injected dose compared to racemic BMIPP.

  • Resolution and in vitro and initial in vivo evaluation of isomers of iodine-125-labeled 1-azabicyclo[2.2.2]oct-3-yl Alpha-hydroxy-Alpha-(1-iodo-1-propen-3-yl)-Alpha-phenylacetate: a high-affinity ligand for the muscarinic receptor.
    Journal of medicinal chemistry, 1995
    Co-Authors: D.w. Mcpherson, Carla R. Lambert, Kristi Jahn, V.k. Sood, Robert C. Mcree, B.r. Zeeberg, Richard C. Reba, F.f. Knapp
    Abstract:

    1-Azabicyclo[2.2.2]oct-3-yl Alpha-hydroxy-Alpha-(1-iodo-1-propen-3-yl)- Alpha-phenylacetate (IQNP, 1), is a highly selective ligand for the muscarinic acetylcholinergic receptor (mAChR). There are eight stereoisomers in the racemic mixture. The optical isomers of Alpha-hydroxy-Alpha-phenyl-Alpha-(1-propyn-3-yl)acetic acid were resolved as the AlphaMethylbenzylamine salts, and the optical isomers of 3-quinuclidinol were resolved as the tartrate salts. The E and Z isomers were prepared by varying the reaction conditions for the stannylation of the triple bond followed by purification utilizing flash column chromatography. In vitro binding assay of the four stereoisomers containing the (R)-(-)-3-quinuclidinyl ester demonstrated that each isomer of 1 bound to mAChR with high affinity. In addition, (E)-(-)-(-)-IQNP demonstrated the highest receptor subtype specificity between the m1 molecular subtype (KD, nM, 0.383 +/- 0.102) and the m2 molecular subtype (29.6 +/- 9.70). In vivo biodistribution studies demonstrated that iodine-125-labeled (E)-(-)-(+)-1 cleared rapidly from the brain and heart. In contrast, iodine-125-labeled (E)-(-)-(-)-, (Z)-(-)-(-)-, and (Z)-(-)-(+)-1 have high uptake and retention in mAChR rich areas of the brain. It was also observed that (E)-(-)-(-)-IQNP demonstrated an apparent subtype selectivity in vivo with retention in M1 (m1, m4) mAChR areas of the rain. In addition, (Z)-(-)-(-)-IQNP also demonstrated significant uptake in tissues containing the M2 (m2) mAChR subtype. These results demonstrate that the iodine-123-labeled analogues of the (E)-(-)-(-)- and (Z)-(-)-(-)-IQNP isomers are attractive candidates for single-photon emission-computed tomographic imaging of cerebral and cardiac mAChR receptor densities.

Richard M. Pagni – One of the best experts on this subject based on the ideXlab platform.

  • A study of the liquid and solvent properties of optically active and racemic AlphaMethylbenzylamine
    The journal of physical chemistry. B, 2007
    Co-Authors: Andrew T. Fischer, Richard M. Pagni, Robert N. Compton
    Abstract:

    Speed-of-sound measurements are reported for RS (racemic) and S liquid α-Methylbenzylamine (MBA) obtained using a modified design of previously published experimental geometry. After correcting for density changes, the resulting isentropic compressibility of the S liquid is found to be 2% larger than that of the RS racemic mixture. These data, along with proton NMR chemical shifts and published partial molar volumes, suggest that the structures of the racemic and optically active liquids are subtly different. The magnitude of the compressibilities and other data such as viscosity and the Kamlet−Taft parameters are consistent with the molecules in the liquids interacting via extensive hydrogen bonding. Cyclohexane, toluene, nitrobenzene, dimethyl sulfoxide, and methanol are completely miscible in MBA, as predicted from their corresponding Hildebrand solubility parameters. Proton NMR, optical rotation, and IR studies were carried out on solutions of the five solutes in MBA as a function of mole fraction. Th…

  • Solvent effects on the optical rotation of (S)-(-)-α-Methylbenzylamine
    The journal of physical chemistry. A, 2006
    Co-Authors: Andrew T. Fischer, Robert N. Compton, Richard M. Pagni
    Abstract:

    The optical rotation of (S)-(-)-AlphaMethylbenzylamine at 589 nm has been measured in 39 different solvents at five different concentrations: 0.25, 0.50, 1.00, 2.00, and 3.00 M. A correlation of the intrinsic rotations (i.e., extrapolation of specific rotations to zero concentration) with Kamlet’s and Taft’s solvent parameters (Alpha, beta, and pi) is established. The polarity/polarizability, pi, and solvent acidity, Alpha, terms are found to have a greater effect upon the optical rotation than the basicity of the solvent, beta. The specific rotation for (S)-(-)-AlphaMethylbenzylamine has been calculated with Gaussian03 using a PCM model (B3LYP aug-cc-pVDZ) for all 39 solvated systems. Comparisons between the experimental and calculated values show the importance of hydrogen bonding on specific rotation.

Robert N. Compton – One of the best experts on this subject based on the ideXlab platform.

  • A study of the liquid and solvent properties of optically active and racemic AlphaMethylbenzylamine
    The journal of physical chemistry. B, 2007
    Co-Authors: Andrew T. Fischer, Richard M. Pagni, Robert N. Compton
    Abstract:

    Speed-of-sound measurements are reported for RS (racemic) and S liquid α-Methylbenzylamine (MBA) obtained using a modified design of previously published experimental geometry. After correcting for density changes, the resulting isentropic compressibility of the S liquid is found to be 2% larger than that of the RS racemic mixture. These data, along with proton NMR chemical shifts and published partial molar volumes, suggest that the structures of the racemic and optically active liquids are subtly different. The magnitude of the compressibilities and other data such as viscosity and the Kamlet−Taft parameters are consistent with the molecules in the liquids interacting via extensive hydrogen bonding. Cyclohexane, toluene, nitrobenzene, dimethyl sulfoxide, and methanol are completely miscible in MBA, as predicted from their corresponding Hildebrand solubility parameters. Proton NMR, optical rotation, and IR studies were carried out on solutions of the five solutes in MBA as a function of mole fraction. Th…

  • Solvent effects on the optical rotation of (S)-(-)-α-Methylbenzylamine
    The journal of physical chemistry. A, 2006
    Co-Authors: Andrew T. Fischer, Robert N. Compton, Richard M. Pagni
    Abstract:

    The optical rotation of (S)-(-)-AlphaMethylbenzylamine at 589 nm has been measured in 39 different solvents at five different concentrations: 0.25, 0.50, 1.00, 2.00, and 3.00 M. A correlation of the intrinsic rotations (i.e., extrapolation of specific rotations to zero concentration) with Kamlet’s and Taft’s solvent parameters (Alpha, beta, and pi) is established. The polarity/polarizability, pi, and solvent acidity, Alpha, terms are found to have a greater effect upon the optical rotation than the basicity of the solvent, beta. The specific rotation for (S)-(-)-AlphaMethylbenzylamine has been calculated with Gaussian03 using a PCM model (B3LYP aug-cc-pVDZ) for all 39 solvated systems. Comparisons between the experimental and calculated values show the importance of hydrogen bonding on specific rotation.