Metabolic Fate of Hallucinogenic NBOMes
Open accessAbstract
2,5-Dimethoxy-N-benzylphenethylamines (NBOMes) are very potent 5-HT2AR agonists. Illicit use of these psychedelic compounds has emerged in recent years, and several fatalities have been linked to their recreational use. In its [(11)C]-labeled form, one NBOMe (25B-NBOMe) was recently developed as a PET-ligand for clinical investigations of 5HT2AR ([(11)C]Cimbi-36). Herein, we have identified the phase I and phase II metabolites of 25B-NBOMe in pigs as well as in humans. We find that the primary route of metabolism is 5'-demethylation, followed by conjugation to glucuronic acid. Carbon-11 labeling of 25B-NBOMe in three different positions followed by in vivo evaluation in pigs and humans corroborated these findings.
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Diemethoxyphenethylamines such as [11C]-Cimbi-36 are metabolized in pigs and humans by demethylation, usually in the 5-position, and subsequently glucuronation.
“The diemethoxyphenethylamines such as [11C]-Cimbi-36 are metabolized in pigs and humans by demethylation, usually in the 5-position, and subsequently glucuronation [116].”
From Molecular and Functional Imaging Studies of Psychedelic Drug Action in Animals and Humans. (2021) · cites this paper as [116]
Cites
Studerus, E., Kometer, M., Hasler, F., & Vollenweider, F. X. (2011) · Journal of Psychopharmacology · doi:10.1177/0269881110382466 · Cited by 532 · see citing works
Psychedelics and mental health: a population study
Krebs, T. S., & Johansen, P.-Ø. (2013) · PLoS ONE · doi:10.1371/journal.pone.0063972 · Cited by 347 · see citing works
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Nichols, D. E. (2016) · Pharmacological Reviews · doi:10.1124/pr.115.011478 · Cited by 1,762 · see citing works
Molecular and Functional Imaging Studies of Psychedelic Drug Action in Animals and Humans.
Cumming, P., Scheidegger, M., Dornbierer, D., Palner, M., Quednow, B. B., & Martin-Soelch, C. (2021) · Molecules · doi:10.3390/molecules26092451 · Cited by 43 · see citing works
- Authors
- Leth-Petersen, S., Gabel-Jensen, C., Gillings, N., Lehel, S., Hansen, H. D., Knudsen, G. M., & Kristensen, J. L.
- Affiliations
- Department of Drug Design and Pharmacology and ‡Department of Pharmacy, University of Copenhagen, DK-2100 Copenhagen, Denmark
- University of Copenhagen (DK)
- Corresponding author
- Kristensen, Jesper L.
- Venue
- Chemical Research in Toxicology
- Publisher
- American Chemical Society (ACS)
- Published
- 2015-12-29
- Volume
- 29
- Issue
- 1
- Pages
- 96-100
- ISSN
- 0893-228X (ISSN-L)
- 1520-5010
- OpenAlex
- W2210848389
- Cited by
- 43
- References
- 2
- Citations by year
- 2026: 1 · 2025: 1 · 2024: 1 · 2023: 2 · 2021: 8 · 2020: 4 · 2019: 6 · 2018: 5 · 2017: 8 · 2016: 7
- FWCI
- 5.31
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Chemical Research in Toxicology (publishedVersion, other-oa)
- PubMed (publishedVersion)
- Research at the University of Copenhagen (University of Copenhagen) (submittedVersion)
- Funders
- Lundbeckfonden
- Topics
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Forensic Toxicology and Drug Analysis
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
- Social Sciences › Psychology › Clinical Psychology › Psychedelics and Drug Studies
- Keywords
- NBOMe, 5-HT2A receptor agonists, hallucinogens, drug metabolism, phase I metabolism, phase II metabolism, glucuronidation, carbon-11 radiolabeling, PET radiotracer
- MeSH terms
- Animals, Hallucinogens, Humans, Microsomes, Liver, Phenethylamines, Swine, Molecular Structure, Positron-Emission Tomography
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