Journal of Medical Toxicology

, Volume 10, Issue 1, pp 45–50 | Cite as

2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25I-NBOMe): Clinical Case with Unique Confirmatory Testing

  • Samuel J. Stellpflug
  • Samantha E. Kealey
  • Cullen B. Hegarty
  • Gregory C. Janis
Toxicology Observation

Abstract

Introduction

2C designer drugs have been in use since the 1970s, but new drugs continue to develop from substitutions to the base phenethylamine structure. This creates new clinical profiles and difficulty with laboratory confirmation. 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25I-NBOMe) is a relatively new 2C drug that is more potent than structural 2C analogs; exposure reports are rare. Testing for 2C drugs is developing; specific testing for new analogs such as 25I-NBOMe is a challenge. These drugs do not reliably trigger a positive result on rapid drug immunoassays. Additionally, most facilities with confirmatory testing capabilities will not identify 25I-NBOMe; methods for detecting 25I-NBOMe in biological samples have not been clearly described nor have optimal metabolic targets for detecting 25I-NBOMe ingestion.

Case Report

An 18-year-old female presented following use of 25I-NBOMe. She had an isolated brief seizure, tachycardia, hypertension, agitation, and confusion. She improved with intravenously administered fluids and benzodiazepines and was discharged 7 h postingestion. Urine was analyzed using quantitative LC-MS/MS methodology for 25I-NBOMe, 2-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)-methyl]ethanamine (25C-NBOMe), and 2-(2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine (25H-NBOMe). 25I-NBOMe was found at a concentration of 7.5 ng/mL, and 25H-NBOMe was detected as well. Additional testing was pursued to characterize the metabolism of 25I-NBOMe; the sample was reanalyzed with UPLC–time-of-flight mass spectrometry to identify excreted metabolites. The sample was additionally analyzed for the presence of 2,5-dimethoxy-4-iodophenethylamine (2C-I), 4-bromo-2,5-dimethoxyphenethylamine (2C-B), and 1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane (2C-E).

Discussion

This is a report of a patient presenting following exposure to 25I-NBOMe, a dangerous member of the evolving 2C drug class. The exposure was confirmed in a unique manner that could prove helpful in guiding further patient analysis and laboratory studies.

Keywords

25-I 25i Phenethylamine Hallucinogen Shulgin 

References

  1. 1.
    Rosenbaum CD, Carreiro SP, Babu KM (2012) Here today, gone tomorrow…and back again? A review of herbal marijuana alternatives (K2, Spice), synthetic cathinones (bath salts), kratom, Salvia divinorum, methoxetamine, and piperazines. J Med Toxicol 8:15–32PubMedCrossRefPubMedCentralGoogle Scholar
  2. 2.
    Shulgin AT, Shulgin A (1991) PIHKAL: a chemical love story. Transform, BerkeleyGoogle Scholar
  3. 3.
    Dean BV, Stellpflug SJ, Burnett AB, Engebretsen KM (2013) 2C or not 2C: phenethylamine designer drug review. J Med Toxicol 9:172–178PubMedCrossRefGoogle Scholar
  4. 4.
    Rupar A (2012) Adam Budge, 18, charged with murder following friend’s synthetic drug overdose. Minneapolis: City Pages [updated 21 Jun 2012]. http://blogs.citypages.com/blotter/2012/06/adam_budge_18_charged_with_murder_following_friends_synthetic_drug_overdose.php. Accessed 16 Feb 2013
  5. 5.
    Walsh P (2012) U.S. indicts four in synthetic drug deaths. Minneapolis: Star Tribune [updated 27 Dec 2012]. http://www.startribune.com/printarticle/?id=184934801. Accessed 16 Feb 2013
  6. 6.
    Erowid.com (2012) 25I-NBOMe (2C-I-NBOMe) fatalities/deaths [updated 12 Sep 2012]. http://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml. Accessed 16 Feb 2013
  7. 7.
    U.S. Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research (CDER), Center for Veterinary Medicine (CVM) (2001) Guide for industry: bioanalytical validation. http://www.fda.gov/downloads/Drugs/Guidances/ucm070107.pdf. Accessed 16 Feb 2013
  8. 8.
    Scientific Working Group for Forensic Toxicology (SWGTOX) (2012) Standard practices for method validation in forensic toxicology. http://www.swgtox.org/documents/Validation_public_comment.pdf. Accessed 16 Feb 2013
  9. 9.
    Drug Enforcement Administration (2011) 4-Bromo-2,5-dimethoxyphenethylamine information sheet. Washington, DC: Drug Enforcement Administration [updated 16 Feb 2011]. http://www.deadiversion.usdoj.gov/drugs_concern/bromo_dmp/bromo_dmp.pdf. Accessed 12 Feb 2013
  10. 10.
    112th Congress (2012) S. 3187: Food and Drug Administration Safety and Innovation Act. Section 1152. Washington, DC: Library of Congress [updated 10 Jul 2012]. http://beta.congress.gov/bill/112th-congress/senate-bill/3187. Accessed 12 Feb 2013
  11. 11.
    Nichols DE (2004) Hallucinogens. Pharmacol Ther 101:131–181PubMedCrossRefGoogle Scholar
  12. 12.
    Nichols DE, Frescas SP, Chemel BR, Rehder KS, Zhong D, Lewin AH (2008) High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high affinity 5-HT2A receptor-selective agonist radioligand. Bioorg Med Chem 16:6116–6123PubMedCrossRefPubMedCentralGoogle Scholar
  13. 13.
    Marek GJ, Wright RA, Schoepp DD, Monn JA, Aghajanian GK (2000) Physiological antagonism between 5-hydroxytryptamine2A and group II metabotropic glutamate receptors in prefrontal cortex. J Pharmacol Exp Ther 292:76–87PubMedGoogle Scholar
  14. 14.
    Braden MR, Parrish JC, Naylor JC, Nichols DE (2007) Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists. Mol Pharmacol 70:1956–1964CrossRefGoogle Scholar
  15. 15.
    Kelly A, Eisenga B, Riley B, Judge B (2012) Case series of 25I-NBOMe exposures with laboratory confirmation. Clin Toxicol 50:70CrossRefGoogle Scholar
  16. 16.
    Rose SR, Cumpston KL, Stromberg PE, Wills BK (2012) Severe poisoning following self-reported use of 25-I, a novel substituted amphetamine. Clin Toxicol 50:70CrossRefGoogle Scholar
  17. 17.
    Rose SR, Poklis JL, Poklis A (2013) A case of 25I-NBOMe (25-I) intoxication: a new potent 5-HT2A agonist designer drug. Clin Toxicol 51(3):174–177CrossRefGoogle Scholar

Copyright information

© American College of Medical Toxicology 2013

Authors and Affiliations

  • Samuel J. Stellpflug
    • 1
    • 2
  • Samantha E. Kealey
    • 1
  • Cullen B. Hegarty
    • 1
  • Gregory C. Janis
    • 3
  1. 1.Clinical Toxicology Service and Department of Emergency MedicineRegions HospitalSt. PaulUSA
  2. 2.Department of Emergency MedicineRegions HospitalSaint PaulUSA
  3. 3.MedTox LaboratoriesSaint PaulUSA

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