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Identification of 1-(thiophene-2-carbonyl)-LSD from blotter paper falsely labeled “1D-LSD”

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Abstract

Purpose

Since the mid-2010s, lysergic acid diethylamide (LSD) analogs made for substance abuse have periodically emerged. In this case, three pieces of blotter paper labeled “1D-LSD” and presumably impregnated with this LSD analog, were seized. Several websites indicate that 1D-LSD is 1-(1,2-dimethylcyclobutane-1-carbonyl)-LSD. Because this analog is much more difficult to synthesize than previously reported LSD analogs, we doubted that the blotter paper contained 1D-LSD. Herein, we determined the structure of the absorbed compound.

Methods

One of the seized specimens was extracted and analyzed using gas chromatography/mass spectrometry (GC/MS), liquid chromatography/mass spectrometry (LC/MS), high-resolution mass spectrometry (HRMS), and nuclear magnetic resonance (NMR) spectroscopy to estimate the extract components. The estimated compound was then synthesized, yielding an authentic standard. The contents of the seized specimens were identified using authentic standard analysis with GC/MS, LC/MS, and NMR spectroscopy.

Results

Instrumental analyses confirmed the active compound to be 1-(thiophene-2-carbonyl)-LSD, which was inconsistent with the labeling on drug-infused blotter paper.

Conclusion

As in this case, similar blotter paper analyses should consider the possibility of a mismatch between the label and ingredient. To the authors’ knowledge, this is the first case report in which 1-(thiophene-2-carbonyl)-LSD was seized and the first seizure of an LSD analog in which an aromatic carboxylic acid had been condensed to LSD. This type of lysergamide may become prevalent in the near future, and we should remain alert for newly appearing lysergamides.

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Acknowledgements

We would like to thank Editage (www.editage.com) for English language editing.

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Authors and Affiliations

  1. Third Department of Forensic Science, National Research Institute of Police Science, 6-3-1 Kashiwanoha, Kashiwa, Chiba, 277-0882, Japan

    Yuki Okada, Hiroki Segawa, Tadashi Yamamuro, Kenji Kuwayama, Kenji Tsujikawa, Tatsuyuki Kanamori & Yuko T. Iwata

  2. Forensic Science Laboratory, Kochi Prefectural Police Headquarters, 2-4-30, Marunouchi, Kochi, Kochi, 780-8544, Japan

    Kazuki Ueno, Noriko Nishiwaki & Toshihiko Nishimura

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  1. Yuki Okada
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  2. Kazuki Ueno
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  10. Yuko T. Iwata
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Correspondence to Yuki Okada.

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Supplementary Information

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Supplementary file 1: Figure S1.

1H NMR spectrum of synthesized 1T-LSD. Figure S2. 13C NMR spectrum of synthesized 1T-LSD. Figure S3. 1H-13C HMBC spectrum (full-scale) of synthesized 1T-LSD. Figure S4. 1H-13C HMBC spectrum (zoom) of synthesized 1T-LSD. Figure S5. TIC and EIC at m/z 433 by GC/MS for a specimen 1, b specimen 2, c specimen 3, and d synthesized 1T-LSD. Figure S6. Mass spectra of the peak with a retention time of 26.2 min by GC/MS for a specimen 1, b specimen 2, c specimen 3, and d synthesized 1T-LSD. Figure S7. TIC by LC/MS of a specimen 1, b specimen 2, c specimen 3, and d synthesized 1T-LSD. Figure S8. Mass spectra of the peak with a retention time of 9.3 min by LC/MS for a specimen 1, b specimen 2, c specimen 3, and d synthesized 1T-LSD.

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Okada, Y., Ueno, K., Nishiwaki, N. et al. Identification of 1-(thiophene-2-carbonyl)-LSD from blotter paper falsely labeled “1D-LSD”. Forensic Toxicol 42, 93–101 (2024). https://doi.org/10.1007/s11419-023-00668-8

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  • DOI: https://doi.org/10.1007/s11419-023-00668-8

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