Influence of substituted tetrahydroisoquinolines and catecholamines on lipolysis, in vitro—II

Shonk, R.F.; Miller, Duane D.; Feller, Dennis R.

doi:10.1016/0006-2952(71)90445-x

Cited by 30 publications

(11 citation statements)

References 14 publications

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“…Optical rotations of the TMQ isomers used in the present study are similar to those reported earlier. 39 Thus, the greater IAR values of the TMQ isomers on guinea pig atria and trachea and on rat white adipose tissue (2.9 log units)39 may be related to a greater enantiomeric purity. Taken collectively, these results suggest that enantiomeric purity differences represent the most likely explanation for the discrepancies in reported eudismic ratios for this p-agonist.…”

Section: Rat Distal Colonmentioning

confidence: 99%

Isomeric‐Activity ratios of trimetoquinol enantiomers on β‐adrenergic receptor subtypes: Functional and biochemical studies

et al. 1994

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Trimetoquinol [1-(3',4',5'-trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4- tetrahydroisoquinoline , TMQ] exists as two enantiomers, and the (-)-(S)-isomer is a potent beta-adrenergic receptor (beta-AR) agonist. Experiments were conducted to examine the functional and biochemical potencies of the (S)-and (R)-enantiomers of TMQ for interaction with beta-AR subtypes in tissues, membrane fractions, and cell systems. The isomeric-activity ratios (IARs) of the TMQ isomers [(S)-isomer > > (R)-isomer] for stimulation of beta 1- and beta 2-AR of guinea pig right atria and trachea were 224 and 1585, respectively; these IARs were similar to those observed on atypical beta-AR systems of rat distal colon (575), rat brown adipocytes (398), but differed from that of rat esophageal smooth muscle (2884) in the presence of pindolol. In the absence of pindolol, the potencies for the TMQ enantiomers were slightly increased; however, the IARs remained unchanged in rat distal colon, rat brown adipocytes, and rat esophageal smooth muscle. Similarly, radioligand binding studies demonstrated that the TMQ isomer beta-AR affinities were stereoselective for the (-)-(S)-isomer in membranes of guinea pig left ventricle (beta 1) and lung (beta 2) giving IARs of 115 and 389, respectively; and in E. coli expressing human beta 1- and beta 2-AR giving IARs of 661 and 724, respectively. Corresponding IARs of receptor affinities and stimulation of cAMP accumulation in Chinese hamster ovary cells expressing human beta 2-AR and rat beta 3-AR were 331 and 282, and 118 and 4678, respectively. These results indicate that the (-)-(S)-isomer of TMQ exhibits high affinity, and is a potent and highly stereoselective agonist for each beta-AR subtype, that the isomers generally fail to differentiate between the beta-AR subtypes, and that, based upon differences in IAR within beta 3-AR containing systems, subtypes of atypical beta (or beta 3)-AR may exist in adipose tissue and smooth muscle.

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Section: Rat Distal Colonmentioning

confidence: 99%

Isomeric‐Activity ratios of trimetoquinol enantiomers on β‐adrenergic receptor subtypes: Functional and biochemical studies

et al. 1994

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“…Some of the substituted tetrahydroisoquinolines are known to produce a variety of pharmacological and biochemical actions on the adrenergic nervous system (Smissman et al, 1976). The pharmacological effects of tetrahydroisoquinolines include lypolytic (Shonk et al, 1971), bronchial relaxant (Miller et al, 1975) and hypotensive activities (Holtz et al, 1964). In recent years, recognition of the importance of tetrahydroisoquinolines as antihypertensive or anti-arrhythmic agents has resulted in increased interest in related compounds (Harrold et al, 1988).…”

Section: Commentmentioning

confidence: 99%

2-(2-Chloroacetyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Ling

Zou

et al. 2006

Acta Cryst E

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“…Some of the substituted tetrahydroisoquinolines are known to produce a variety of pharmacological and biochemical actions on the adrenergic nervous system (Smissman et al, 1976). The pharmacological effects of tetrahydroisoquinolines include lypolytic (Shonk et al, 1971), bronchial relaxant (Miller et al, 1975) and hypotensive activities (Holtz et al, 1964). We report here the crystal structure of the title compound, (I), which is a substituted tetrahydroisoquinoline.…”

Section: Commentmentioning

confidence: 99%

2-(2-Chloroacetyl)-6,7-dimethoxy-1-(phenoxymethyl)-1,2,3,4-tetrahydroisoquinoline

2007

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Influence of substituted tetrahydroisoquinolines and catecholamines on lipolysis, in vitro—II

Cited by 30 publications

References 14 publications

Isomeric‐Activity ratios of trimetoquinol enantiomers on β‐adrenergic receptor subtypes: Functional and biochemical studies

Isomeric‐Activity ratios of trimetoquinol enantiomers on β‐adrenergic receptor subtypes: Functional and biochemical studies

2-(2-Chloroacetyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

2-(2-Chloroacetyl)-6,7-dimethoxy-1-(phenoxymethyl)-1,2,3,4-tetrahydroisoquinoline

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