Showing papers by "F. Ivy Carroll published in 1994"
TL;DR: In this article, 4-hydroxy-N-methylisoquinolinium iodide with triethylamine in tetrahydrofuran or acetonitrile forms 2-methyl-4-oxidoisoquinium (2) in situ.
18 citations
TL;DR: In this article, a radiotracer was prepared by N-benzylation of (+)-cis-N-normetazocine with [α-11C]-benzmanyl iodide in ethanol using sodium hydrogen carbonate as the proton acceptor.
Abstract: (+)-N-[11C]-Benzyl-N-normetazocine (1S,5S,9S-(+)-cis-2-[11C]-benzyl-2′-hydroxy-5,9-dimethyl-6,7-benzomorphan), a potent and selective ligand for the σ receptor, was prepared by N-benzylation of (+)-cis-N-normetazocine with [α-11C]-benzyl iodide in ethanol using sodium hydrogen carbonate as the proton acceptor. The radiotracer was purified by semi-preparative reverse-phase HPLC. The average specific activity was 746 mCi/μmol calculated at end-of-synthesis (EOS). The average time of synthesis including formulation was 35 minutes.
10 citations
TL;DR: It is demonstrated that the novel pyrrole RTI‐4793‐14 is a selective, high affinity ligand for PCP site 2 and provides further support for an association between PCPSite 2 and the BATs.
Abstract: [3H]TCP, an analog of the dissociative anesthetic phencyclidine (PCP), binds with high affinity to two sites in guinea pig brain membranes, one that is MK-801 sensitive and one that is not. The MK-801-sensitive site (PCP site 1) is associated with NMDA receptors, whereas the MK-801-insensitive site (PCP site 2) may be associated with biogenic amine transporters (BAT). Although several “BAT ligands” are known that bind selectively to PCP site 2 and not to PCP site 1 (such as indatraline), these compounds have low affinity for site 2 (Ki values > 1 μ). Here we demonstrate that the novel pyrrole RTI-4793-14 is a selective, high affinity ligand for PCP site 2. We determined the IC50 values of RTI-4793-14 and several reference compounds [PCP, (+)-MK801 and indatraline] for PCP site 1 (assayed with [3H](+)-MK801), PCP site 2 (assayed with [3H]TCP in the presence of 500 nM (+)-MK801) and a variety of BAT-related measures ([3H]CFT binding to the DA transporter, [3H]nisoxetine binding to the norepinephrine transporter, [3H]dopamine uptake, [3H]serotonin uptake). In addition, we determined the ability of RTI-4793-14 to block NMDA responses in cultured hippocampal neurons under voltage clamp. (+)-MK801 had high affinity for PCP site 1 (4.6 nM) and potently inhibited NMDA-induced responses, but was much less potent in the BAT-related measures (IC50s > 10 μ). PCP had high affinity at PCP site 1 (IC50 = 92 nM) and PCP site 2 (IC50 = 117 nM), and was moderately potent in all BAT-related measures except [3H]nisoxetine binding. Indatraline was potent in BAT-related measures (IC50s, 2 to 5 nM), but weak in other measures (IC50s > 1 μ). In contrast, RTI-4793-14 had high affinity for PCP site 2 (38 nM), low affinity for PCP site 1 (> 36 μ), moderate IC50s for all BAT-related measures, and negligible activity at NMDA receptors. Viewed collectively, these data indicate that RTI-4793-14 binds with high affinity and selectivity to PCP site 2 and provide further support for an association between PCP site 2 and the BATs. © 1994 Wiley-Liss, Inc.
6 citations
TL;DR: The first stereo and enantioselective syntheses of trans-9-alkyl-2-benzyl-5-methyl-6,7-benomorphans were described in this article.
5 citations
TL;DR: In this article, the tritiation of aryl compounds with tritium gas was conducted on the underivatized substrate, and a new method was presented for the trithiation of tritia with trithium gas, which was combined directed ortho metallation and facile reduction of the carbonpotassium bond.
Abstract: A new method is presented for the tritiation of aryl compounds with tritium gas which is conducted on the underivatized substrate. Combined directed ortho metallation and facile reduction of the carbonpotassium bond affords incorporation of tritium at high specific activity under mild conditions. The metallation/reduction method is demonstrated for the preparation of [3H]ibogaine.
4 citations
TL;DR: In this paper, the asymmetric synthesis starting with (1R, 2R)-or (1S, 2S)-1-hydroxymethyl-2-alkyl-1,2-dihydronaphthalene is described.
Abstract: 9-Alkyl 6,7-benzomorphans (1,2,3,4,5,6-hexahydro-11-alkyl-2,6-methano-3-benzazocines) are important selective ligands of sigma receptor sites; their asymmetric synthesis starting with (1R, 2R)- or (1S, 2S)-1-hydroxymethyl-2-alkyl-2-alkyl-1,2-dihydronaphthalene is described.
4 citations