Forensic Toxicology

, Volume 34, Issue 1, pp 166–173 | Cite as

A phenethylamine derivative 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(3,4-methylenedioxyphenyl)methyl]ethanamine (25I-NB34MD) and a piperazine derivative 1-(3,4-difluoromethylenedioxybenzyl)piperazine (DF-MDBP), newly detected in illicit products

  • Nahoko Uchiyama
  • Ruri Kikura-Hanajiri
  • Takashi Hakamatsuka
Original Article


Two new psychoactive substances (NPSs), a phenethylamine derivative 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(3,4-methylenedioxyphenyl)methyl]ethanamine (25I-NB34MD, 1) and a piperazine derivative 1-(3,4-difluoromethylenedioxybenzyl)piperazine (DF-MDBP, 2), were identified in illicit products distributed from January to March 2015 in Japan. The identification was based on liquid chromatography–mass spectrometry (LC–MS), gas chromatography–mass spectrometry (GC–MS), high-resolution MS and nuclear magnetic resonance (NMR) analyses. Compound 1 has a 3,4-methylenedioxybenzyl moiety that is an analog of N-benzylmethoxy derivatives of 2,5-dimethoxyphenethylamines (“NBOMe”-compounds), e.g., 25I-NBOMe. Compound 2 is a difluoromethylenedioxy analog of the known designer drug 1-(3,4-methylenedioxybenzyl)piperazine (MDBP). To our knowledge, this is the first report of compounds 1 and 2 detected as NPSs in illicit products. Although there is no chemical or pharmaceutical information for compound 1, a 2,3-methylenedioxy isomer of 1, 25I-NBMD, was reported to have a binding affinity for 5-HT2A receptor. In the GC–MS and LC–MS analyses, compound 1 (25I-NB34MD) showed spectra that are very similar to those of the isomer 25I-NBMD. The structure of compound 1 was determined here by an NMR analysis. Considering these results, we should be careful when analyzing NPSs in illicit products to prevent their misidentification as isomers of other NPSs. It is important to directly compare an unknown substance with an authentic substance by using multiple instruments such as GC–MS and LC–MS.


2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(3,4-methylenedioxyphenyl)methyl]ethanamine (25I-NB34MD) 1-(3,4-difluoromethylenedioxybenzyl)piperazine (DF-MDBP) New psychoactive substance Illicit product Phenethylamine Piperazine 



A portion of this work was supported by a Health and Labor Sciences Research Grant from the Ministry of Health, Labour, and Welfare, Japan.

Compliance with ethical standards

Conflicts of interest

There are no financial or other relations that could lead to a conflict of interest.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.


  1. 1.
    EMCDDA (2015) EMCDDA-Europol 2014 Annual Report on the implementation of council decision 2005/387/JHA, July 2015. Accessed Nov 2015
  2. 2.
    UNODC (2015) Global SMART update 2015—vol 14, September 2015. Accessed Nov 2015
  3. 3.
    Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014) Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products identified in illegal products. Forensic Toxicol 32:105–117CrossRefGoogle Scholar
  4. 4.
    EMCDDA (2014) EMCDDA–Europol Joint Report on a new psychoactive substance: 25I-NBOMe. EMCDDA-Europol, Lisbon, January 2014. Accessed Nov 2015
  5. 5.
  6. 6.
    Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) URB-754: a new class of designer drug and 12 synthetic cannabinoids detected in illegal products. Forensic Sci Int 227:21–32PubMedCrossRefGoogle Scholar
  7. 7.
    Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products. Forensic Toxicol 31:223–240CrossRefGoogle Scholar
  8. 8.
    Zuba D, Sekula K (2013) Analytical characterization of three hallucinogenic N-(2-methoxy)benzyl derivatives of the 2C-series of phenethylamine drugs. Drug Test Anal 5:634–645PubMedCrossRefGoogle Scholar
  9. 9.
    Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM (2011) Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers. Eur J Nucl Med Mol Imaging 38:681–693PubMedCrossRefGoogle Scholar
  10. 10.
    Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (2014) Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chem Neurosci 5:243–249PubMedPubMedCentralCrossRefGoogle Scholar
  11. 11.
    Liu J, Fitzgerald AE, Mani NS (2012) Reductive amination by continuous-flow hydrogenation: direct and scalable synthesis of a benzylpiperazine. Synthesis 44:2469–2473CrossRefGoogle Scholar

Copyright information

© Japanese Association of Forensic Toxicology and Springer Japan 2015

Authors and Affiliations

  • Nahoko Uchiyama
    • 1
  • Ruri Kikura-Hanajiri
    • 1
  • Takashi Hakamatsuka
    • 1
  1. 1.National Institute of Health SciencesTokyoJapan

Personalised recommendations