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Chemical Compound Review

Benodain     1-(7,10- dioxabicyclo[4.4.0]deca- 1,3,5...

Synonyms: Benodaine, Piperoxan, Piperoxane, Piperoxano, Piperoxanum, ...
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Disease relevance of Benodaine

  • Piperoxane (10 and 20 mg/kg, IP) significantly potentiated PTZ-induced tonic seizures and mortality [1].
  • Piperoxan (150 micrograms/kg i.v. or 10 micrograms/kg i.a. vert.) given 15 min after St 91 (16 micrograms/kg i.a. vert.) reduced both the hypotension and bradycardia [2].
  • Infusion of St 91 (4--16 microgram/kg over 2 min) into the vertebral artery (i.a. vert.) produced dose-dependent hypotension and bradycardia only, which were reversed by piperoxan (300 microgram/kg, intracisternal) [3].
  • Hypothermia was inhibited by piperoxan injected intracisternally (10 millimicron/kg) but not intraperitoneally (10 and 50 millimicron/kg) [4].
  • S 3341 reduced the tachycardia resulting from stimulation of the cardioaccelerator nerve in the anaesthetized, spinalised and bilateraly vagotomised dog, this effect was reversed by piperoxan [5].

Psychiatry related information on Benodaine


High impact information on Benodaine

  • The direct effect of alpha 2-autoreceptors was studied by measuring the effects of piperoxan, an alpha 2-autoreceptor antagonist, and clonidine, an agonist on catecholamine exocytosis, from single bovine chromaffin cells in culture [8].
  • Administration of the alpha 2-adrenoceptor antagonist piperoxane failed to produce any changes in either of these parameters, suggesting that at least in vitro the afterhyperpolarization and postactivation inhibition seen in locus coeruleus neurons do not result from the activation of alpha 2-adrenoceptors [9].
  • The comparison of long-term change in tyrosine hydroxylase values after piperoxane, RU24722, clonidine, and combined RU24722-clonidine treatment demonstrated that an activation during a few hours did not induce tyrosine hydroxylase in central noradrenergic neurons [10].
  • This PRL increase was maximal 15 min after piperoxane infusion and significant, when compared with baseline levels, in the +15, +30, +45, +60, and +90-min samples [11].
  • Thus, infusion into the locus coeruleus of the alpha-2 agonist clonidine, but not the alpha-2 antagonist piperoxane, eliminated behavioral depression.(ABSTRACT TRUNCATED AT 250 WORDS)[12]

Chemical compound and disease context of Benodaine


Biological context of Benodaine

  • Low i.v. doses of piperoxane and rauwolscine dramatically increased SND and produced a concomitant rise in mean arterial pressure and heart rate [16].
  • Brainstem mechanisms in the modulation of the sympathetic baroreflex by piperoxan [17].
  • Piperoxan (5 micrograms) injected bilaterally into the ventrolateral pressor area did not change blood pressure or the rate of sympathetic discharge [17].
  • The alpha 2-adrenoceptor antagonists piperoxan and idazoxan inhibited the yawning response without affecting the penile erections [18].
  • Apart from piperoxan and its analogues, which showed some preference for alpha 2-adrenergic binding sites, all benzodioxane-like structures displayed a general selectivity for the alpha 1-adrenoreceptor sites labeled with 3H-prazosin [19].

Anatomical context of Benodaine


Associations of Benodaine with other chemical compounds


Gene context of Benodaine

  • It has been suggested that the stimulation of the secretion of PRL by the alpha 2 adrenergic receptor antagonists (yohimbine, piperoxane) results from blockade of an inhibitory influence imposed on PRL release by the central alpha 2 receptors (7, 15) [28].
  • However, the alpha 2 antagonists yohimbine and piperoxan, the alpha 2 agonists medetomidine, guanfacine, and guanabenz, the non-specific alpha antagonist phentolamine, and the alpha 1 antagonist prazosin did not disinhibit conflict responding in the Vogel lick-shock paradigm [29].
  • S 3341 reduced hypertension and tachycardia due to stimulation of the sympathetic outflow in the pithed rat, an effect also antagonised by piperoxan [5].

Analytical, diagnostic and therapeutic context of Benodaine

  • Similarly, microinjection of the alpha-2 adrenergic antagonist piperoxan (10 nmol) decreased the duration (from 45 +/- 8 to 23 +/- 4 min), but not the magnitude of the sympathoinhibitory response [30].
  • 2 At concentrations greater than 2 x 10(-4) M, piperoxan produced a rise in perfusion pressure, a contraction of the splenic capsule, and a marked dose-dependent decrease in transmitter overflow [31].
  • A capillary electrophoresis (CE) study of the separation of Piperoxan enantiomers was carried out in order to find the buffer conditions that produce the maximum peak separation time between the two enantiomers and the optimal chiral selector concentration [32].
  • Prazosin, a specific post-synaptic alpha 1 adrenoceptor blocker, induced hypothermia whereas piperoxan (presynaptic alpha 2 antagonist) produced hyperthermia [33].
  • The inhibitory effects produced by iontophoresis of alpha-MNE or Clo were reduced to the same degree (86-98%) by iontophoresis of idazoxan (an alpha 2-adrenergic antagonist with imidazoline structure) and by iontophoresis of piperoxan (65-77%, a nonimidazoline alpha 2-antagonist) [34].


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  2. Effects of prazosin and piperoxan on central cardiovascular actions of St 91 in cats. McLennan, P.L., Bentley, G.A. Eur. J. Pharmacol. (1982) [Pubmed]
  3. Studies on the cardiovascular depressor actions of ST 91--an analogue of clonidine. McLennan, P.L., Bentley, G.A. Eur. J. Pharmacol. (1978) [Pubmed]
  4. The hypothermic effect of clonidine and other imidazolidines in relation to their ability to enter the central nervous system in mice. McLennan, P.L. Eur. J. Pharmacol. (1981) [Pubmed]
  5. Pharmacological properties of (N-dicyclopropylmethyl) amino-2-oxazoline (S 3341), an alpha-2 adrenoceptor agonist. Laubie, M., Poignant, J.C., Scuvée-Moreau, J., Dabire, H., Dresse, A., Schmitt, H. Journal de pharmacologie. (1985) [Pubmed]
  6. Dipropylacetate-induced quasi-morphine abstinence behaviour in the rat: suppression by alpha 2-adrenoceptor stimulation. van der Laan, J.W., Weick, G., Hillen, F.C. Psychopharmacology (Berl.) (1983) [Pubmed]
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  10. Long-term effects of RU24722 on tyrosine hydroxylase of the rat brain. Labatut, R., Richard, F., Milne, B., Quintin, L., Lecestre, D., Pujol, J.F. J. Neurochem. (1988) [Pubmed]
  11. Effect of piperoxane on serum prolactin: possible role of epinephrine-mediated synapses in the inhibition of prolactin secretion. Gold, M.S., Donabedian, R.K., Redmond, D.E. Endocrinology (1978) [Pubmed]
  12. Reversal of behavioral depression by infusion of an alpha-2 adrenergic agonist into the locus coeruleus. Simson, P.G., Weiss, J.M., Hoffman, L.J., Ambrose, M.J. Neuropharmacology (1986) [Pubmed]
  13. Evidence for involvement of alpha 2-adrenoceptors in the nucleus ambiguous in baroreflex-mediated bradycardia. Gurtu, S., Sharma, D.K., Sinha, J.N., Bhargava, K.P. Naunyn Schmiedebergs Arch. Pharmacol. (1983) [Pubmed]
  14. Effects of drugs interfering with the metabolism of octopamine on blood pressure of rats. Delbarre, B., Delbarre, G., Casset-Senon, D., Sestillange, P. Comp. Biochem. Physiol. C, Comp. Pharmacol. (1982) [Pubmed]
  15. Pharmacological characteristics of spinal alpha-adrenoreceptors in rats. Connor, H.E., Drew, G.M., Finch, L., Hicks, P.E. Journal of autonomic pharmacology. (1981) [Pubmed]
  16. Evidence for a central sympathoexcitatory action of alpha-2 adrenergic antagonists. McCall, R.B., Schuette, M.R., Humphrey, S.J., Lahti, R.A., Barsuhn, C. J. Pharmacol. Exp. Ther. (1983) [Pubmed]
  17. Brainstem mechanisms in the modulation of the sympathetic baroreflex by piperoxan. Laubie, M., Schmitt, H. Eur. J. Pharmacol. (1988) [Pubmed]
  18. Antagonism of drug-induced yawning and penile erections in rats. Gower, A.J., Berendsen, H.H., Broekkamp, C.L. Eur. J. Pharmacol. (1986) [Pubmed]
  19. Selectivity of benzodioxane alpha-adrenoceptor antagonists for alpha 1- and alpha 2-adrenoceptors determined by binding affinity. Timmermans, P.B., van Kemenade, J.E., Batink, H.D., van Zwieten, P.A. Pharmacology (1983) [Pubmed]
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  30. Blockade of alpha-2 adrenergic receptors in the rostral ventrolateral medulla attenuates the sympathoinhibitory response to cocaine. Abrahams, T.P., Liu, W., Varner, K.J. J. Pharmacol. Exp. Ther. (1996) [Pubmed]
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  32. Continuous fractionation of enantiomer pairs in free solution using an electrophoretic analog of simulated moving bed chromatography. Thome, B., Ivory, C.F. Journal of chromatography. A. (2002) [Pubmed]
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