Analysis of octopamine in human doping control samples

Biomedical Chromatography

Volumn 26, Issue 5, 2012, Pages 610-615

  Thevis, Mario ^a   Koch, Anja ^a   Sigmund, Gerd ^a   Thomas, Andreas ^a   Schänzer, Wilhelm ^a  

^a GERMAN SPORT UNIVERSITY COLOGNE   (Germany)

Author keywords

Bitter orange; Citrus aurantium; Doping; Mass spectrometry; Sport; Stimulants; Synephrine

Indexed keywords

BODY FLUIDS; DIETARY SUPPLEMENTS; ELECTROSPRAY IONIZATION; FOOD ADDITIVES; LIQUID CHROMATOGRAPHY; NUTRITION; PHASE SEPARATION; PHENOLS; SPORTS; VITAMINS;

1-HYDROXYETHYL; BIOGENIC AMINES; BITTE ORANGE; CITRUS AURANTIUM; CONTROL SAMPLES; DOPING CONTROL; NUTRITIONAL SUPPLEMENTS; STIMULANT; SYNEPHRINE; URINE SAMPLE;

MASS SPECTROMETRY;

CATION EXCHANGE RESIN; OCTOPAMINE; OXEDRINE;

ARTICLE; CONTROLLED STUDY; DIET SUPPLEMENTATION; DOPING; DRUG DETERMINATION; DRUG URINE LEVEL; ELECTROSPRAY MASS SPECTROMETRY; LIMIT OF DETECTION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SOLID PHASE EXTRACTION; URINALYSIS;

CITRUS AURANTIUM; INVERTEBRATA;

EID: 84859442255     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.1705     Document Type: Article

References (35)

1. Axelrod J and Saavedra JM. Octopamine. Nature 1977; 265: 501-504.
2. Boulton AA and Davis BA. The metabolism of ingested deuterium-labelled p-tyramine in normal subjects. Biomedical & Environmental Mass Spectrometry 1987; 14: 207-211.
3. Brandau K and Axelrod J. The biosynthesis of octopamine. Naunyn Schmiedeberg's Archives of Pharmacology 1972; 273: 123-133.
4. 3H by rat brain. Biochemical Pharmacology 1969; 18: 863-869.
5. Brown CM, McGrath JC, Midgley JM, Muir AG, O'Brien JW, Thonoor CM, Williams CM and Wilson VG. Activities of octopamine and synephrine stereoisomers on alpha-adrenoceptors. British Journal of Pharmacology 1988; 93: 417-429.
6. Carpene C, Galitzky J, Fontana E, Atgie C, Lafontan M and Berlan M. Selective activation of beta3-adrenoceptors by octopamine: comparative studies in mammalian fat cells. Naunyn Schmiedeberg's Archives of Pharmacology 1999; 359: 310-321.
7. Erspamer V. Adrenaline-like action of extracts of posterior salivary glands of Octopus vulgaris irradiated with ultraviolet light. Archivio di Scienze Biologiche 1940; 26: 443-468.
8. Erspamer V. Active substances in the posterior salivary glands of Octopoda. II. Tyramine and octopamine (oxyoctopamine). Acta Pharmacologica et Toxicologica 1948; 4: 224-247.
9. Erspamer V. Identification of octopamine as l-p-hydroxyphenylethanolamine. Nature 1952; 169: 375-376.
10. Fontana E, Morin N, Prevot D and Carpene C. Effects of octopamine on lipolysis, glucose transport and amine oxidation in mammalian fat cells. Comparative Biochemistry and Physiology. Part C, Pharmacology, Toxicology & Endocrinology 2000; 125: 33-44.
11. Fugh-Berman A and Myers A. Citrus aurantium, an ingredient of dietary supplements marketed for weight loss: current status of clinical and basic research. Experimental Biology and Medicine 2004; 229: 698-704.
12. Haaz S, Fontaine KR, Cutter G, Limdi N, Perumean-Chaney S and Allison DB. Citrus aurantium and synephrine alkaloids in the treatment of overweight and obesity: an update. Obesity Reviews 2006; 7: 79-88.
13. 3H-synephrine. Arzneimittel-Forschung 1978; 28: 2326-2331.
14. Hengstmann JH, Konen W, Konen C, Eichelbaum M and Dengler HJ. The physiological disposition of p-octopamine in man. Naunyn Schmiedeberg's Archives of Pharmacology 1974; 283: 93-106.
15. Hengstmann JH, Konen W, Konen C, Eichelbaum M and Dengler HJ. Bioavailability of m-octopamine in man related to its metabolism. European Journal of Clinical Pharmacology 1975; 8: 33-39.
16. Ibrahim KE, Couch MW, Williams CM, Budd MB, Yost RA and Midgley JM. Quantitative measurement of octopamines and synephrines in urine using capillary column gas chromatography negative ion chemical ionization mass spectrometry. Analytical Chemistry 1984; 56: 1695-1699.
17. Kubo K, Kiyose C, Ogino S and Saito M. Suppressive effect of Citrus aurantium against body fat accumulation and its safety. Journal of Clinical Biochemistry and Nutrition 2005; 36: 11-17.
18. Kuske FA. Treatment of hypotensive regulation disturbances by Norphen. Therapie der Gegenwart 1969; 108: 1460-1462.
19. Kusu F, Matsumoto K, Arai K and Takamura K. Determination of synephrine enantiomers in food and conjugated synephrine in urine by high-performance liquid chromatography with electrochemical detection. Analytical Biochemistry 1996; 235: 191-194.
20. Nelson BC, Putzbach K, Sharpless KE and Sander LC. Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium). Journal of Agricultural and Food Chemistry 2007; 55: 9769-9775.
21. Penzak SR, Jann MW, Cold JA, Hon YY, Desai HD and Gurley BJ. Seville (sour) orange juice: synephrine content and cardiovascular effects in normotensive adults. Journal of Clinical Pharmacology 2001; 41: 1059-1063.
22. Pisano JJ, Creveling CR and Udenfriend S. Enzymic conversion of para-tyramine to para-hydroxyphenylethanolamine (norsynephrin). Biochimica et Biophysica Acta 1960; 43: 566-568.
23. Putzbach K, Rimmer CA, Sharpless KE, Wise SA and Sander LC. Determination of bitter orange alkaloids in dietary supplement standard reference materials by liquid chromatography with atmospheric-pressure ionization mass spectrometry. Analytical and Bioanalytical Chemistry 2007; 389: 197-205.
24. Sander LC, Sharpless KE, Satterfield MB, Ihara T, Phinney KW, Yen JH, Wise SA, Gay ML, Lam JW, McCooeye M, Gardner G, Fraser C, Sturgeon R and Roman M. Determination of ephedrine alkaloids in dietary supplement standard reference materials. Analytical Chemistry 2005; 77: 3101-3112.
25. Santana J, Sharpless KE and Nelson BC. Determination of para-synephrine and meta-synephrine positional isomers in bitter orange-containing dietary supplements by LC/UV and LC/MS/MS. Food Chemistry 2008; 109: 675-682.
26. Stucke W. Therapy of hypotensive circulatory disorders with Norphen retard. Zeitschrift für Allgemeinmedizin 1972; 48: 240-243.
27. Stur O. Therapy of hypotonic ciruclatory dysregulation in school children using Novadral retard. Münchener Medizinische Wochenschrift 1971; 113: 1563-1567.
28. Thomas A, Sigmund G, Guddat S, Schänzer W and Thevis M. Determination of selected stimulants in urine for sports drug analysis by solid phase extraction via cation exchange and means of liquid chromatography-tandem mass spectrometry. European Journal of Mass Spectrometry 2008; 14: 135-143.
29. Visentin V, Morin N, Fontana E, Prevot D, Boucher J, Castan I, Valet P, Grujic D and Carpene C. Dual action of octopamine on glucose transport into adipocytes: inhibition via beta3-adrenoceptor activation and stimulation via oxidation by amine oxidases. Journal of Pharmacology and Experimental Therapeutics 2001; 299: 96-104.
30. Watson DG, Midgley JM, Chen RN, Huang W, Bain GM, McDonald NM, Reid JL and McGhee CN. Analysis of biogenic amines and their metabolites in biological tissues and fluids by gas chromatography-negative ion chemical ionization mass spectrometry (GC-NICIMS). Journal of Pharmaceutical and Biomedical Analysis 1990; 8: 899-904.
31. Williams CM, Couch MW, Thonoor CM and Midgley JM. Isomeric octopamines: their occurrence and functions. Journal of Pharmacy and Pharmacology 1987; 39: 153-157.
32. World Anti-Doping Agency. The 2008 Monitoring Program, 2008. Available from:
33. World Anti-Doping Agency. The 2009 Monitoring Program, 2009. Available from:
34. World Anti-Doping Agency. The 2010 Prohibited List, 2010. Available from:
35. World Anti-Doping Agency. Laboratory Statistics 2003-2009, 2011. Available from: