Abstract
A specific and sensitive liquid chromatography-electrospray ionization mass spectrometry method was developed for the determination of ibogaine and noribogaine in human urine. The work-up procedure involved a solid phase extraction of the compounds and the internal standard (fluorescein) using Oasis HLB columns. The system used a Zorbax eclipse XDB C8 analytical column packed with 5µm diameter particles as the stationary phase. The mobile phase consisted of a 20-min gradient (mobile phase A: 0.02% (v/v) trimethylamine in acetonitrile, mobile phase B: 2 mM ammonium formate buffer (pH 3)). Mass spectrometric data were acquired in single ion monitoring mode at m/z 311.1, 297.2 and 333 for ibogaine, noribogaine and fluorescein, respectively. The drug/internal standard peak area ratios were linked via a quadratic relationship to concentrations (1.78−358 μg L−1 for ibogaine; 2−400 μg L−1 for noribogaine). Precision ranged from 5.8 to 14.8% and accuracy was between 93.2 and 112.9%. Mean extraction recoveries of ibogaine, noribogaine and fluorescein were 70.0, 81.7 and 94.8%, respectively. The extraction efficiency was independent of concentration over the range studied. The lower limits of quantitation were 1.78 μg L−1 for ibogaine and 2 μg L−1 for noribogaine. In this paper, extensive stability testing was undertaken using a wide range of storage conditions. This method was found suitable for urine analysis of a poisoning involving ingestion of drink made from powdered root of shrub Tabernanthe iboga.
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References
Zubaran C (2000) CNS Drug Reviews 6: 219
Naranjo C (1969) Clin, Toxicol, 2:209
Goutarel R, Gollnhoffer O, Sillans R (1993) Psychedelic Monogr, Essays 6:71
Popik P, Skolnick P (1999) “Pharmacology of ibogaine and ibogaine-related alkaloids” in: “The alkaloids”, Cordell G.A., (ed) Academic Press, SanDiego, p. 197
Glick SD, Kuehne ME, Raucci J, Wilson TE, Larson E, Keller RW, Carlson JN (1994) Brain Res 657:14
Glick SD, Pearl SM, Cai J, Maisonneuve IM (1996) Brain Res 713:294
Glick SD, Maisonneuve IM (1998) Ann NY Acad Sci 844:214
Glick SD, Maisonneuve IM (2000) Ann NY Acad Sci 909:88
Mash DC, Kovera CA, Buck BE, Norenberg MD, Shapshak P, Hearn WL, Sanchez-Ramos J (1998) Ann NY Acad Sci 844:274
Mash DC, Kovera CA, Pablo J, Tyndale RF, Ervin FD, Williams IC, Singleton EG, Mayor M (2000) Ann NY Acad Sci 914:394
Mash DC, Kovera CA, Pablo J, Tyndale R, Ervin FR, Kamlet JD, Hearn WL (2001) Alkaloids 56:155.
Maisonneuve IM, Visker KE, Mann GL, Bandarage UK, Kuehne ME, Glick SD (1997) Eur, J, Pharmacol, 336:123
Wei D, Maisonneuve IM, Kuehne ME, Glick SD, (1998) Brain Res 800:260
Cappendijk SLT, Dzoljic MR (1993) Eur J Pharmacol 241:261
Rezvani AH, Overstreet DH, Lee YW (1995) Pharmacol Biochem Behav 52:615
Baumann MH, Pablo J, Ali SF, Rothman RB, Mash DC (2001) Alkaloids 56:79
Baumann MH, Rothman RB, Pablo J, Mash DC (2001) J Pharmacol ExpTher 297:531
Baumann MH, Pablo JP, Ali SF, Rothman RB, Mash DC, (2000) Ann NY Acad Sci 914:354
Obach RS, Pablo JP, Mash DC, (1998) Drug Metab Dispo 26:764
Pearl SM, Herrick-Davis K, Teitler M, Glick SD, (1995) Brain Res 675:342
Pablo JP, Mash DC, (1998) NeuroReport 9 109
Maisonneuve IM, Keller RW, Glick SD (1992) Brain Res 579:87
Dagnino D, Schripsema J, Peltenburg A, Verpoorte R, Teunis K (1991) J Nat Prod 54:1558
Cartoni GP, Giarusso A (1972) J Chromatogr 71:154
Gallagher CA, Hough LB, Keefner SM, Seyed-Mozaffari A, Archer S, Glick SD (1995) Biochem Pharmacol 49:73
Ley FR, Jeffcoat AR, Thomas BF (1996) J Chromatogr A 723:101
Hearn WL, Pablo J, Hime GW, Mash DC, (1995) J Anal Toxicol 19:427
Alburges ME, Foltz RL, Moody DE (1995) J Anal Toxicol 19:381
Bogusz MJ, Maier RD, Kruger KD, Kohls U, (1998) J Anal Toxicol 22:549
Kontrimavièiûtë V, Larroque M, Briedis V, Margout D, Bressolle F (2005) J Chromatogr B Analyt Technol Biomed Life Sci 822:285
Kontrimavièiûtë V, Breton H, Mathieu O, Balas L, Escale R, Mathieu-Daudé JC, Bressolle F, (2006) J Chromatogr B Analyt Technol Biomed Life Sci accepted
US Food and Drug Administration. Guidance for industry. Bioanalytical method validation. May 2001.(Accessed May 2004)
United States Pharmacopoeia XXXIII, The United States Pharmacopoeia Convention, Rockville, Md, 2003, p. 2439
Shah VP, Midha KK, Dighe S, McGilveray IJ, Skelly JP, Yacobi A, Layloff T, Viswanathan CT, Cook CE, McDowall RD, Pittman KA, Spector S (1992) J Pharm Sci 81:309
Bressolle F, Bromet-Petit M, Audran MJ, (1996) Chromatogr B 686:3
Matuszewski BK, Constanzer ML, (1998) Anal Chem 70:882
Taylor WI, “The iboga and Vocanca alkaloids” IN: “The alkaloids”, R.H.F. Manske (ed) Vol VIII. Chemistry and Physiology. Academic Press, New York/London, 1965, p. 203
Mikatos A, Panderi I (2004) Anal Chim Acta 505:107
Clivio P, Richard B, Deverre JR, Sevenet T, Zeches M, Le Men-Oliver L (1991) Phytochemistry 30:3785
Jenks CW (2002) Natural Product Letters 16: 71
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V. Kontrimavičiūtė and H. Breton contributed equally to this work.
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Kontrimavičiūtė, V., Breton, H., Barnay, F. et al. Liquid Chromatography-Electrospray Mass Spectrometry Determination of Ibogaine and 12-Hydroxy-Ibogamine in Human Urine. Chroma 63, 533–541 (2006). https://doi.org/10.1365/s10337-006-0795-9
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DOI: https://doi.org/10.1365/s10337-006-0795-9