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Chemical Compound Review

Tropanol     8-methyl-8- azabicyclo[3.2.1]octan-3-ol

Synonyms: Tropine, Pseudotropine, Pseudotropanol, psi-Tropine, ARONIS24186, ...
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Disease relevance of Pseudotropanol

  • Growth of Pseudomonas AT3 on the alkaloid atropine as its sole source of carbon and nitrogen is nitrogen-limited and proceeds by degradation of the tropic acid part of the molecule, with the metabolism of the tropine being limited to the point of release of its nitrogen [1].
  • The recombinant TRII protein expressed in Escherichia coli catalyzes pseudotropine formation from tropinone with a Km value, a pH optimum, substrate and co-substrate preferences similar to those reported for the TRII enzymes from other Solanaceae species [2].
  • Pseudotropine, the major alkaloid, is known to affect motility and might represent a causative agent for the observed cases of equine intestinal fibrosis [3].
  • Metabolism of the tropine indole-3-carboxylate ICS 205-930 by differentiated rat and human hepatoma cells [4].

Psychiatry related information on Pseudotropanol

  • Of these, the benzofurane-3-carboxylic ester of tropine (1) was found powerfully to increase the pain threshold, with a cholinergic mechanism of action [5].

High impact information on Pseudotropanol


Biological context of Pseudotropanol


Anatomical context of Pseudotropanol

  • These and earlier results suggest a possible form of metabolic dependence of myelin on tropine substances from the axon [13].
  • Whereas vagal stimulation caused a muscarinic receptor-mediated increase in tracheal smooth muscle tone (as indicated by a 9.6 +/- 1.1 mmHg increase in endotracheal cuff pressure), the increase in cuff pressure (1.8 +/- 0.4 mmHg) was attenuated after intrapericardial tropine (4 mg) [14].
  • The metabolism of the tropine indole-3-carboxylate ICS 205-930 (ICS), a highly potent and selective antagonist of 5-HT3 receptors, was investigated in continuous cell lines derived from rat or human liver and compared to the in vivo metabolism in rat and human [4].

Associations of Pseudotropanol with other chemical compounds


Gene context of Pseudotropanol

  • Intrathecal administration of the 5-HT3 receptor antagonist tropine (200 microg) produced allodynia, reduced the threshold, decreased the latency, and increased the number of spikes in the late component of the nociceptive flexion reflex [19].
  • Poisoning with tropine alkaloids from cultivated plants and pharmaceuticals is an uncommon cause of delirium and coma [20].
  • The tropine-forming reductase (TR I, EC was purified 108-fold, the pseudotropine-forming enzyme (TR II, EC was purified 3410-fold to homogeneity [21].


  1. The isolation and identification of 6-hydroxycyclohepta-1,4-dione as a novel intermediate in the bacterial degradation of atropine. Bartholomew, B.A., Smith, M.J., Long, M.T., Darcy, P.J., Trudgill, P.W., Hopper, D.J. Biochem. J. (1993) [Pubmed]
  2. Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.). Keiner, R., Kaiser, H., Nakajima, K., Hashimoto, T., Dräger, B. Plant Mol. Biol. (2002) [Pubmed]
  3. Tropane alkaloids and toxicity of Convolvulus arvensis. Todd, F.G., Stermitz, F.R., Schultheis, P., Knight, A.P., Traub-Dargatz, J. Phytochemistry (1995) [Pubmed]
  4. Metabolism of the tropine indole-3-carboxylate ICS 205-930 by differentiated rat and human hepatoma cells. Fischer, V., Baldeck, J.P., Wiebel, F.J. Molecular toxicology. (1987) [Pubmed]
  5. Synthesis and biological activity of a series of aryl tropanyl esters and amides chemically related to 1H-indole-3-carboxylic acid endo 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester. Development of a 5-HT4 agonist endowed with potent antinociceptive activity. Romanelli, M.N., Ghelardini, C., Dei, S., Matucci, R., Mori, F., Scapecchi, S., Teodori, E., Bartolini, A., Galli, A., Giotti, A. Arzneimittel-Forschung. (1993) [Pubmed]
  6. Structure-activity relationships among derivatives of dicarboxylic acid esters of tropine. Gyermek, L. Pharmacol. Ther. (2002) [Pubmed]
  7. Structure of tropinone reductase-II complexed with NADP+ and pseudotropine at 1.9 A resolution: implication for stereospecific substrate binding and catalysis. Yamashita, A., Kato, H., Wakatsuki, S., Tomizaki, T., Nakatsu, T., Nakajima, K., Hashimoto, T., Yamada, Y., Oda, J. Biochemistry (1999) [Pubmed]
  8. Structure-activity relationship in a new series of atropine analogues. 1. N,N'-Disubstituted 6,7-diazabicyclo[3.2.2]nonane derivatives. Cherkez, S., Yellin, H., Kashman, Y., Yaavetz, B., Sokolovsky, M. J. Med. Chem. (1979) [Pubmed]
  9. The formation of 3 alpha- and 3 beta-acetoxytropanes by Datura stramonium transformed root cultures involves two acetyl-CoA-dependent acyltransferases. Robins, R.J., Bachmann, P., Robinson, T., Rhodes, M.J., Yamada, Y. FEBS Lett. (1991) [Pubmed]
  10. Determination of distribution coefficients for some 5-HT3 receptor antagonists by reversed-phase high-performance liquid chromatography. Kugel, C., Heintzelmann, B., Wagner, J. Journal of chromatography. A. (1994) [Pubmed]
  11. Integrated pharmacokinetics and pharmacodynamics of atropine in healthy humans. II: Pharmacodynamics. Hinderling, P.H., Gundert-Remy, U., Schmidlin, O., Heinzel, G. Journal of pharmaceutical sciences. (1985) [Pubmed]
  12. Receptor binding studies of soft anticholinergic agents. Huang, F., Buchwald, P., Browne, C.E., Farag, H.H., Wu, W.M., Ji, F., Hochhaus, G., Bodor, N. AAPS PharmSci (2001) [Pubmed]
  13. Axon-myelin transfer of glycerol-labeled lipids and inorganic phosphate during axonal transport. Ledeen, R.W., Haley, J.E. Brain Res. (1983) [Pubmed]
  14. Intrapericardial blocking agents have extracardiac effects in dogs. Mittelstadt, S.W., O'Hagan, K.P., Bell, L.B., Clifford, P.S. Am. J. Physiol. (1994) [Pubmed]
  15. Atropine- and scopolamine-resistant subtypes of muscarinic receptors in the rabbit aorta. Manjeet, S., Sim, M.K. Eur. J. Pharmacol. (1989) [Pubmed]
  16. Effects of Exogenous Polyamines on Tropane Alkaloid Production by a Root Culture of Duboisia myoporoides. Yoshioka, T., Yamagata, H., Ithoh, A., Deno, H., Fujita, Y., Yamada, Y. Planta Med. (1989) [Pubmed]
  17. Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism. Dräger, B. Phytochemistry (2006) [Pubmed]
  18. Brassicaceae contain nortropane alkaloids. Brock, A., Herzfeld, T., Paschke, R., Koch, M., Dräger, B. Phytochemistry (2006) [Pubmed]
  19. Role of 5-HT3 receptors in the mechanisms of central pain syndrome. Kukushkin, M.L., Igon'kina, S.I. Bull. Exp. Biol. Med. (2003) [Pubmed]
  20. Datura delirium. Hanna, J.P., Schmidley, J.W., Braselton, W.E. Clinical neuropharmacology. (1992) [Pubmed]
  21. The reduction of tropinone in Datura stramonium root cultures by two specific reductases. Portsteffen, A., Dräger, B., Nahrstedt, A. Phytochemistry (1994) [Pubmed]
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