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Chemical Compound Review

Oxedrine     4-(1-hydroxy-2-methylamino- ethyl)phenol

Synonyms: Simpalon, Simpatol, Sympatol, Synefrin, Analeptin, ...
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Disease relevance of Sympaethamin


Psychiatry related information on Sympaethamin

  • We studied the effects of p-synephrine on the immobility behaviors and on the spontaneous motor activity in mice. p-Synephrine at oral doses from 1 to 10 mg/kg significantly decreased the duration of immobility in the tail suspension test and the forced swimming test in mice [5].

High impact information on Sympaethamin

  • These effects are not likely caused by C. aurantium alone, because an eightfold higher dose of synephrine (Advantra Z) had no effect on blood pressure, but may be attributable to caffeine and other stimulants in the multi-component formulation [6].
  • Dose-adjusted synephrine pharmacokinetics were similar between treatments with t(max) = 90 min, t(1/2) = 3.0 hours, V/F = 16347 L, and CL/F = 88.9 L/min for Xenadrine EFX [6].
  • Other good inhibitors of N-acetyltransferase included desipramine, synephrine, and an experimental insecticide, CGA 132427 [7].
  • 3. The phenolamines, octopamine and synephrine were only able to couple the alpha 2A-adrenoceptor to a dose-dependent decrease in cyclic AMP production at concentrations up to 1 mM, with the synephrine isomers being more potent than the corresponding octopamine isomers [8].
  • The potency of each (+)- form was 1-2 orders of magnitude less than that of the (-) counterpart, the differences being greater for the stereoisomers of synephrine than for those of octopamine on both alpha 1- and alpha 2-adrenoceptors [9].

Chemical compound and disease context of Sympaethamin


Biological context of Sympaethamin


Anatomical context of Sympaethamin


Associations of Sympaethamin with other chemical compounds


Gene context of Sympaethamin

  • All urine specimens demonstrated a negative response to the CEDIA Amphetamines Assay. Urine specific gravity ranged from 1.007 to 1.028, and pH ranged from 5.0 to 7.0; thus, reducing the possibility that the negative results were caused by diluted specimens or reduced excretion of synephrine into alkaline urine [21].

Analytical, diagnostic and therapeutic context of Sympaethamin


  1. Exactly which synephrine alkaloids does Citrus aurantium (bitter orange) contain? Allison, D.B., Cutter, G., Poehlman, E.T., Moore, D.R., Barnes, S. International journal of obesity (2005) (2005) [Pubmed]
  2. Mode of action of synephrine on Xanthomonas oryzae. William, F., Mahadevan, A. Indian J. Exp. Biol. (1980) [Pubmed]
  3. Elusive amines and primary headaches: historical background and prospectives. D'Andrea, G., Terrazzino, S., Fortin, D., Cocco, P., Balbi, T., Leon, A. Neurol. Sci. (2003) [Pubmed]
  4. Citrus aurantium and synephrine alkaloids in the treatment of overweight and obesity: an update. Haaz, S., Fontaine, K.R., Cutter, G., Limdi, N., Perumean-Chaney, S., Allison, D.B. Obesity reviews : an official journal of the International Association for the Study of Obesity. (2006) [Pubmed]
  5. Antidepressant-like effects of p-synephrine in mouse models of immobility tests. Song, D.K., Suh, H.W., Jung, J.S., Wie, M.B., Son, K.H., Kim, Y.H. Neurosci. Lett. (1996) [Pubmed]
  6. Hemodynamic effects of ephedra-free weight-loss supplements in humans. Haller, C.A., Benowitz, N.L., Jacob, P. Am. J. Med. (2005) [Pubmed]
  7. Octopamine uptake and metabolism in the insect nervous system. Wierenga, J.M., Hollingworth, R.M. J. Neurochem. (1990) [Pubmed]
  8. Selective inhibition of adenylyl cyclase by octopamine via a human cloned alpha 2A-adrenoceptor. Airriess, C.N., Rudling, J.E., Midgley, J.M., Evans, P.D. Br. J. Pharmacol. (1997) [Pubmed]
  9. Activities of octopamine and synephrine stereoisomers on alpha-adrenoceptors. Brown, C.M., McGrath, J.C., Midgley, J.M., Muir, A.G., O'Brien, J.W., Thonoor, C.M., Williams, C.M., Wilson, V.G. Br. J. Pharmacol. (1988) [Pubmed]
  10. Fructus aurantii reduced portal pressure in portal hypertensive rats. Huang, Y.T., Wang, G.F., Chen, C.F., Chen, C.C., Hong, C.Y., Yang, M.C. Life Sci. (1995) [Pubmed]
  11. Third place--Resident Clinical Science Award 1990. The in vivo and in vitro effect of phenylephrine (Neo Synephrine) on nasal ciliary beat frequency and mucociliary transport. Phillips, P.P., McCaffrey, T.V., Kern, E.B. Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery. (1990) [Pubmed]
  12. Targets of octopamine action in the lobster: cyclic nucleotide changes and physiological effects in hemolymph, heart and exoskeletal muscle. Battelle, B.A., Kravitz, E.A. J. Pharmacol. Exp. Ther. (1978) [Pubmed]
  13. A role for alternative pathway catecholamines in the regulation of steroidogenesis in cow luteal cells. Battista, P.J., Condon, W.A. J. Reprod. Fertil. (1986) [Pubmed]
  14. Distribution of biogenic amines in the cricket central nervous system. Nagao, T., Tanimura, T. Anal. Biochem. (1988) [Pubmed]
  15. Beta-adrenergic activities of octopamine and synephrine stereoisomers on guinea-pig atria and trachea. Jordan, R., Midgley, J.M., Thonoor, C.M., Williams, C.M. J. Pharm. Pharmacol. (1987) [Pubmed]
  16. Applications of LC-MS in the study of the uptake, distribution, metabolism and excretion of bioactive polyphenols from dietary supplements. Barnes, S., Prasain, J.K., Wang, C.C., Moore, D.R. Life Sci. (2006) [Pubmed]
  17. A rapid liquid chromatography electrospray ionization mass spectrometry(n) method for evaluation of synephrine in Citrus aurantium L. samples. Mattoli, L., Cangi, F., Maidecchi, A., Ghiara, C., Tubaro, M., Traldi, P. J. Agric. Food Chem. (2005) [Pubmed]
  18. An isotopically labeled internal standard liquid chromatography-tandem mass spectrometry method for determination of ephedrine alkaloids and synephrine in dietary supplements. Gay, M.L., Niemann, R.A., Musser, S.M. J. Agric. Food Chem. (2006) [Pubmed]
  19. Acute tubular necrosis associated with chromium picolinate-containing dietary supplement. Wani, S., Weskamp, C., Marple, J., Spry, L. The Annals of pharmacotherapy. (2006) [Pubmed]
  20. Determination of hesperidin and synephrine in Pericarpium Citri Reticulatae by capillary electrophoresis with electrochemical detection. Chen, G., Zhang, L., Zhao, J., Ye, J. Analytical and bioanalytical chemistry. (2002) [Pubmed]
  21. Response of CEDIA amphetamines assay after a single dose of bitter orange. Nguyen, D.T., Bui, L.T., Ambrose, P.J. Therapeutic drug monitoring. (2006) [Pubmed]
  22. Drug-induced changes in catecholaminergic cells of the fish retina. Negishi, K., Laufer, M., Drujan, B.D. J. Neurosci. Res. (1980) [Pubmed]
  23. Determination of synephrine enantiomers in food and conjugated synephrine in urine by high-performance liquid chromatography with electrochemical detection. Kusu, F., Matsumoto, K., Arai, K., Takamura, K. Anal. Biochem. (1996) [Pubmed]
  24. Characterization of antidepressant-like effects of p-synephrine stereoisomers. Kim, K.W., Kim, H.D., Jung, J.S., Woo, R.S., Kim, H.S., Suh, H.W., Kim, Y.H., Song, D.K. Naunyn Schmiedebergs Arch. Pharmacol. (2001) [Pubmed]
  25. Localization of fluorescent compounds in the firefly light organ. Smalley, K.N., Tarwater, D.E., Davidson, T.L. J. Histochem. Cytochem. (1980) [Pubmed]
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