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Chemical Compound Review

Bacticin     1,2,3,4-tetrahydronaphthalene

Synonyms: TETRALIN, Tetranap, Tetralina, Tetraline, tetralene, ...
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Disease relevance of tetralin


Psychiatry related information on tetralin

  • The most effective agents were the dialkylated tetralin derivatives and the N-propyl benzo[g]quinoline compound (0.025-0.5 micrograms); inhibition of motor activity generally decreased as dose was increased [5].
  • The effects of the dopamine D3/D2 receptor agonists quinpirole, quinelorane and (+/-)7-OH-DPAT [(+/-) 7-hydroxy-2(N,N-di-n-propylamino) tetralin] on intracranial self-stimulation (ICSS) were investigated [6].
  • Indicative of anxiolytic effects the 5-HT1A agonists, buspirone, gepirone and 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT) all significantly increased social interaction time and open arm exploration time in the social interaction and elevated plus maze procedures, respectively [7].
  • The PSNs recorded in this study exhibited: (1) progressive decrease in discharge rate from waking to NREM to REM sleep; (2) long action potential duration, and (3) reduction of discharge rate after systemic administration of a selective 5-HT(1A) agonist, (+/-)-8-hydroxy-2-(di-n-propylamino) tetralin hydrobromide (8-OH-DPAT) [8].
  • 1. The effect of chronic administration of antidepressants and electroconvulsive shock (ESC) on the hypothermic response (HTR) induced by 8-hydroxy-2-(di-n-propyramino) tetralin (8-OH-DPAT) as an index of the function of 5-HT1A receptors was investigated in the rat [9].

High impact information on tetralin

  • In an attempt to identify the presynaptic autoreceptor directly, we synthesized the tritiated derivative of 8-hydroxy-2-(di-n-propylamino) tetralin (PAT), a new tetralin derivative with potent 5-HT agonist properties and carried out binding studies with rat brain membranes [10].
  • Mutants resistant to a mixture of xylene and tetralin were isolated from the ahpC mutant but not from the wild-type strain [1].
  • This cAMP increase in cumulus cells could be mimicked by 5-HT agonists with the following order of potency: 5-HT > 8-hydroxy-2-(di-n-propylamino) tetralin = alpha-methyl-5-HT = 5-carboxamidotryptamine maleate > 2-[1-(4-piperonyl)piperazinyl]benzo-triazole, thereby supporting a preferential involvement of 5-HT7 receptors [11].
  • The 6,7-unsubstituted congener (+/-)-(trans)-1-phenyl-3-dimethylamino-1,2,3,4- tetrahydronaphthalene stimulated tyrosine hydroxylase by as much as 50-60% over basal activity, without displacement of dopamine [12].
  • Buspirone (IC50 = 24 nM) and TVX Q 7821 (IC50 = 9.5 nM) display the highest affinity for 5-hydroxytryptamine1A (5-HT1A) binding sites labeled by 3H-8-hydroxy-2-(di-n-pro-pylamino) tetralin (DPAT) [13].

Chemical compound and disease context of tetralin


Biological context of tetralin

  • The maximal number of binding sites labelled by [3H]WAY-100635 was approximately 36% higher compared with that of 8-hydroxy-2-(di-n-[3H]-propylamino) tetralin ([3H]8-OH-DPAT) [18].
  • Seven derivatives of 2-[[2-(3,4-dihydroxyphenyl)-1-methylethyl]amino]-6,7-dihydroxy-1,2,3,4- tetrahydronaphthalene, an inotropic agent which also causes a decrease in blood pressure, were synthesized and tested for inotropic potency, cardioselectivity, and inotropic selectivity [19].
  • New potent prolyl endopeptidase inhibitors: synthesis and structure-activity relationships of indan and tetralin derivatives and their analogues [20].
  • A method was used which involved cyclization of 3,5-dimethoxybenzylsuccinic acid derivatives with pyridinium poly(HF) and subsequent modification of the tetralin ring [21].
  • Absolute bioavailabilities in the rat for the ethyl ester prodrug derivatives of the tetralin, tetralone, and benzopyran analogues of 3 were 28%, 23%, and 24%, respectively [22].

Anatomical context of tetralin

  • Extracellular 5-hydroxytryptamine in median raphe nucleus of the conscious rat is decreased by nanomolar concentrations of 8-hydroxy-2-(di-n-propylamino) tetralin and is sensitive to tetrodotoxin [23].
  • Preincubation of transfected HeLa cell membranes with Ab-2 antibodies revealed two affinity binding sites of the 5-HT1A receptor (KDH = 0.54 +/- 0.09 nM and KDL = 13.74 +/- 4.9 nM) for the agonist 8-hydroxy-2-(di-n-[3H]propylamino) tetralin ([3H]8-OH-DPAT) binding, but Ab-1 and Ab-12 revealed only one site (KD of approximately 2.5 nM) [24].
  • The selective 5-HT1A agonist 8-hydroxy-2(di-n-propylamino) tetralin (8-OHDPAT) increased 3H-5-HT release from aged rat spinal cord slices similar to results previously obtained from adult rat spinal cord slices [25].
  • Injections of tetralin (0.1 micrograms) not only into the nucleus accumbens but also into the tuberculum olfactorium, septal nucleus, anterior olfactory nucleus, anteromedial fibre system, claustrum and caudate-putamen could effect inhibition of motor activity [5].
  • The effectiveness of dopamine decreased with a delayed onset when injections were made anterior or posterior to the substantia nigra; this spectrum of reduced and delayed responding was also apparent when dopamine and the tetralin compound were injected 1 or 2 mm above the nigra [14].

Associations of tetralin with other chemical compounds

  • Nonpeptidic angiotensin II antagonists: synthesis and in vitro activity of a series of novel naphthalene and tetrahydronaphthalene derivatives [26].
  • In addition, the presence of an oxygen-containing substituent at the 8-position of the tetralin ring is not necessary for good affinity, and secondary amines and tertiary amines displayed equal affinity at central 5-HT1A binding sites [27].
  • Because we have now demonstrated that amine substituents larger than propyl, and an unsubstituted 8-position, are well tolerated by central 5-HT1A sites, future studies aimed at the development of new serotonergic tetralin analogues need not be limited to N-propyl or 8-hydroxy derivatives of 2-aminotetralin [27].
  • These effects of morphine was attenuated by the 5HT1A receptor agonists, 8-OH-DPAT [(+)-8-hydroxy-2(di-n-propylamino tetralin HBr] and ipsapirone [28].
  • In contrast, none of the 5HT uptake inhibitors (alaproclate, clomipramine and fluoxetine) or direct agonists ((+/-)-1-(4-iodo-2,5-dimethoxyphenyl)-2-aminopropane, (+/-)-8-hydroxy-2-(di-N-propylamino) tetralin and quipazine) increased fixed-interval response rate, nor did the 5HT uptake inhibitors maintain self-administration [29].

Gene context of tetralin

  • The tetralin derivative 8-OH-DPAT, a drug with selective affinity for 5-HT1A binding sites, was a weak partial agonist on veins and completely devoid of any activity on the platelets [30].
  • Propranolol impaired neither the hypothermia induced by an agonist at the 5-HT 1A receptors: 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT) nor the increase in spontaneous motor activity induced by an agonist at the 5-HT 1B receptors: 5-methoxy-3(1,2,3,6-tetrahydropyridin-4-yl)1-H indole (Ru 24,969) [31].
  • The mixed 5-HT(1A/7) receptor agonist, R(+)-8-hydroxy-2-(di-n-propylamino) tetralin hydrobromide (8-OH-DPAT), reduced the evoked EPSC amplitude in both wild-type and 5-HT1B receptor knockout mice [32].
  • The 5-HT1A agonist 8-hydroxy-2-(di-N-propylamino) tetralin hydrobromide (8-OH-DPAT) mimicked the hyperpolarizing response [33].
  • The synthesis and binding profile on 5-HT1A, 5-HT2, D-1, D-2, alpha 1, and alpha 2 receptors of the N-4 long-chain arylpiperazines 22-40 are reported, where an amino or amido function is inserted into the intermediate chain linked to the alpha position of the tetralin nucleus [34].

Analytical, diagnostic and therapeutic context of tetralin

  • Discharge activity of REM-on neurons was almost completely suppressed by local microdialysis perfusion of the selective 5-HT1A agonist 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT), although this agonist had minimal or no effect on the Wake/REM-on neurons [35].
  • Microinjection of the 5-HT1A agonist 8-hydroxy-2-(di-N-propylamino) tetralin (DPAT; 0.1-10 microg/0.5 microl/side) or the 5-HT1A antagonist WAY 100635 (0.01-1.0 microg/0.5 microl/side) into the VTA or SNR did not substitute for the systemic cocaine cue [36].
  • Identification of an extradiol dioxygenase involved in tetralin biodegradation: gene sequence analysis and purification and characterization of the gene product [37].
  • 1. We studied whether the stimulation of 5-HT1A receptors by 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT), a specific 5-HT1A receptor agonist, reduced electroencephalographic (EEG) seizures induced by intrahippocampal injection of 0.04 microgram in 0.5 microliter of the glutamate analogue kainic acid in freely-moving rats [38].
  • Similarly, quantitative autoradiography using the radiolabeled 5-HT(1A) receptor agonist 8-hydroxy-2-(di-N-propylamino) tetralin demonstrated a significant decline in receptor density in 3- and 13-month MC and HC groups as compared to age-matched LC groups in the hippocampus [39].


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