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Chemical Compound Review

Etobedolum     2-[2-[(4- ethoxyphenyl)methyl]-5- nitro...

Synonyms: etonitazin, Etonitazene, Etonitazeno, Etonitazine, Etonitazenum, ...
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Disease relevance of Etonitazine


Psychiatry related information on Etonitazine


High impact information on Etonitazine

  • Moreover, we have recently demonstrated that the high-efficacy agonist etonitazene promotes rapid endocytosis of micro-opioid receptors, whereas the agonist morphine and the low-efficacy agonist buprenorphine fail to promote detectable receptor endocytosis in micro-opioid receptor expressing HEK293 cells [10].
  • The 5'D-II activity was significantly enhanced 30 min after administration of etonitazene in the frontal cortex, amygdala and limbic forebrain, and after administration of ethanol in the amygdala alone [11].
  • The apparent in vivo dissociation constant (KA) and relative efficacy values for alfentanil, etonitazene, morphine, and nalbuphine were determined by comparing the effects of these agonists in the presence of buprenorphine with the effects of these agonists alone in the rhesus monkey tail-withdrawal procedure [12].
  • To assess the acquisition and maintenance of opioid reinforced behavior, oral self-administration of the potent benzimidazole opioid, etonitazene, was determined using an operant fixed-ratio schedule of reinforcement (FR 8) [3].
  • C-CAM produced dose-dependent rightward and slight downward shifts of the etonitazene dose-effect curve [13].

Biological context of Etonitazine

  • These findings demonstrate genetic differences in opioid reinforcement of operant behavior and indicate that genotype can be an important determinant of whether etonitazene serves as a reinforcer [14].

Anatomical context of Etonitazine

  • Effects of etonitazene consumption and abstinence on the signal transmission of mu-opioid receptors in brain membranes of rats [15].

Associations of Etonitazine with other chemical compounds

  • These results indicate that heroin, 6-acetylmorphine, fentanyl and etonitazine all can produce analgesia through a novel mu analgesic system which is similar to that activated by morphine-6 beta-glucuronide [16].
  • However, diltiazem failed to alter the analgesic potencies of the mu-opioid receptor agonists, fentanyl, etonitazene, nalbuphine, the kappa-opioid receptor agonist, U-50,488 [(trans)-3, 4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)-cyclohexyl]benzeneacetamide ], or the non-opioid, clonidine [17].

Gene context of Etonitazine

  • Antisense mapping of the mu opioid receptor MOR-1 reveals that oligodeoxynucleotide probes against exon 2, which are inactive against morphine analgesia, block morphine-6 beta-glucuronide, heroin, fentanyl and etonitazine analgesia [16].
  • Furthermore, naloxone, but not etonitazene, resulted in a significant increase in the Bmax of TCP binding to the PCP receptor [18].
  • Two groups of naive, male, albino rats derived from different genetic strains (Sprague-Dawley and Wistar) were given a 5 micrograms/ml etonitazene solution as their only available liquid [19].

Analytical, diagnostic and therapeutic context of Etonitazine

  • Together with data previously obtained in drug discrimination and analgesia assays, results of the present study demonstrating homogeneous pA2 values for quadazocine with alfentanil, etonitazene, EKC and Mr2033 strongly suggest that the latter two compounds decrease respiratory function in rhesus monkeys by acting on mu receptors [20].
  • Reinforcing effects of contingently administered subcutaneous injections of etonitazene in rats [21].
  • In all strains, only the paired treatment condition demonstrated tolerance to the analgesic effects of etonitazene compared to the control groups [22].


  1. Etonitazene as a reinforcer: oral intake of etonitazene by rhesus monkeys. Carroll, M.E., Meisch, R.A. Psychopharmacology (Berl.) (1978) [Pubmed]
  2. Determinants of increased drug self-administration due to food deprivation. Carroll, M.E., Meisch, R.A. Psychopharmacology (Berl.) (1981) [Pubmed]
  3. Opioid operant self-administration, analgesia, stimulation and respiratory depression in mu-deficient mice. Elmer, G.I., Pieper, J.O., Goldberg, S.R., George, F.R. Psychopharmacology (Berl.) (1995) [Pubmed]
  4. Differential motor effects of intraventricular infusion of morphine and etonitazene. Shizgal, P., Sklar, L.S., Brown, Z.W., Amit, Z. Pharmacol. Biochem. Behav. (1977) [Pubmed]
  5. Food deprivation increases oral and intravenous drug intake in rats. Carroll, M.E., France, C.P., Meisch, R.A. Science (1979) [Pubmed]
  6. Etonitazene. An improved synthesis. Carroll, F.I., Coleman, M.C. J. Med. Chem. (1975) [Pubmed]
  7. Etonitazene as a reinforcer for rats: increased etonitazene-reinforced behavior due to food deprivation. Meisch, R.A., Kliner, D.J. Psychopharmacology (Berl.) (1979) [Pubmed]
  8. Effect of dose on increased etonitazene self-administration by rats due to food deprivation. Carroll, M.E., Boe, I.N. Psychopharmacology (Berl.) (1984) [Pubmed]
  9. Concurrent etonitazene and water intake in rats: role of taste, olfaction, and auditory stimuli. Carroll, M.E., Meisch, R.A. Psychopharmacology (Berl.) (1979) [Pubmed]
  10. Development of tolerance and sensitization to different opioid agonists in rats. Grecksch, G., Bartzsch, K., Widera, A., Becker, A., Höllt, V., Koch, T. Psychopharmacology (Berl.) (2006) [Pubmed]
  11. Effects of acute administration of ethanol and the mu-opiate agonist etonitazene on thyroid hormone metabolism in rat brain. Baumgartner, A., Pinna, G., Hiedra, L., Bauer, F., Wolf, J., Eravci, M., Prengel, H., Brödel, O., Schmidt, G., Meinhold, H. Psychopharmacology (Berl.) (1998) [Pubmed]
  12. Buprenorphine antagonism of mu opioids in the rhesus monkey tail-withdrawal procedure. Walker, E.A., Zernig, G., Woods, J.H. J. Pharmacol. Exp. Ther. (1995) [Pubmed]
  13. Irreversible opioid antagonist effects of clocinnamox on opioid analgesia and mu receptor binding in mice. Burke, T.F., Woods, J.H., Lewis, J.W., Medzihradsky, F. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
  14. Etonitazene delivered orally serves as a reinforcer for Lewis but not Fischer 344 rats. Suzuki, T., George, F.R., Meisch, R.A. Pharmacol. Biochem. Behav. (1992) [Pubmed]
  15. Effects of etonitazene consumption and abstinence on the signal transmission of mu-opioid receptors in brain membranes of rats. May, T., Juilfs, F., Wolffgramm, J. Neurosci. Lett. (1999) [Pubmed]
  16. Novel receptor mechanisms for heroin and morphine-6 beta-glucuronide analgesia. Rossi, G.C., Brown, G.P., Leventhal, L., Yang, K., Pasternak, G.W. Neurosci. Lett. (1996) [Pubmed]
  17. Diltiazem enhances the analgesic but not the respiratory depressant effects of morphine in rhesus monkeys. Kishioka, S., Ko, M.C., Woods, J.H. Eur. J. Pharmacol. (2000) [Pubmed]
  18. Rat brain PCP receptors: alterations in binding parameters following chronic administration of opiate agonists and antagonists. Byrd, J.C., Bykov, V., Rothman, R.B. Neuropeptides (1987) [Pubmed]
  19. Food deprivation reveals strain differences in opiate intake of Sprague-Dawley and Wistar rats. Carroll, M.E., Pederson, M.C., Harrison, R.G. Pharmacol. Biochem. Behav. (1986) [Pubmed]
  20. Apparent pA2 analysis on the respiratory depressant effects of alfentanil, etonitazene, ethylketocyclazocine (EKC) and Mr2033 in rhesus monkeys. Butelman, E.R., France, C.P., Woods, J.H. J. Pharmacol. Exp. Ther. (1993) [Pubmed]
  21. Reinforcing effects of contingently administered subcutaneous injections of etonitazene in rats. Gomez, T.H., Meisch, R.A. Psychopharmacology (Berl.) (2000) [Pubmed]
  22. Genetic factors in conditioned tolerance to the analgesic effects of etonitazene. Elmer, G.I., Mathura, C.B., Goldberg, S.R. Pharmacol. Biochem. Behav. (1993) [Pubmed]
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