C30-NBOMe

C30-NBOMe
Clinical data
Other namesN-(3,4,5-Trimethoxybenzyl)-4-chloro-2,5-dimethoxyphenethylamine; 25C-NB345OMe; 30C-NBOMe
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 2-(4-chloro-2,5-dimethoxyphenyl)-N-[(3,4,5-trimethoxyphenyl)methyl]ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H26ClNO5
Molar mass395.88 g·mol−1
3D model (JSmol)
  • COC1=CC(=CC(=C1OC)OC)CNCCC2=CC(=C(C=C2OC)Cl)OC
  • InChI=1S/C20H26ClNO5/c1-23-16-11-15(21)17(24-2)10-14(16)6-7-22-12-13-8-18(25-3)20(27-5)19(9-13)26-4/h8-11,22H,6-7,12H2,1-5H3
  • Key:ZQYYVTABADQBTJ-UHFFFAOYSA-N

C30-NBOMe, or 30C-NBOMe, also known as N-(3,4,5-trimethoxybenzyl)-4-chloro-2,5-dimethoxyphenethylamine or as 25C-NB345OMe, is a serotonin receptor modulator of the phenethylamine, 2C, and 25-NB (NBOMe) families.[1][2][3] It is an analogue of 25C-NBOMe with three methoxy groups on the benzyl ring, located at the 3, 4, and 5 positions.[1][2][3][4] The drug was encountered as a novel designer drug in Sweden in 2013.[4][1] However, C30-NBOMe showed greater than or equal to 1,000-fold lower potency as a serotonin 5-HT2A receptor agonist in vitro compared to conventional 25-NB drugs like 25I-NBOMe and 25B-NBOMe (EC50Tooltip half-maximal effective concentration = 1,251 nM vs. 0.40–1.2 nM, respectively).[3] Its affinity for the serotonin 5-HT2A receptor was similarly low (Ki = 515 nM, versus 0.82 nM for 25C-NBOMe).[5] The chemical identification of C30-NBOMe has been studied and described.[2][6][7]

See also

References

  1. 1 2 3 Awuchi CG, Aja MP, Mitaki NB, Morya S, Amagwula IO, Echeta CK, et al. (2 February 2023). "New Psychoactive Substances: Major Groups, Laboratory Testing Challenges, Public Health Concerns, and Community-Based Solutions". Journal of Chemistry. 2023: 1–36. doi:10.1155/2023/5852315. ISSN 2090-9071.
  2. 1 2 3 Martin M, Germaine D, Tracy E, Chepaitis P (13 November 2015), "Analytical Profile of 30C-NBOMe" (PDF), Forensic Drug Review, Cayman Chemical Company, 30C-NBOMe is a N-alkylated analogue of the phenethylamine 2C-C, a known hallucinogen that stimulates monoamine receptor activity and inhibits the reuptake of serotonin (IC50 = 31uM) and norepinephrine (IC50 = 63uM) in rat brain synaptosomes.1,2 30C-NBOMe exhibits a 3,4,5 tri-methoxy benzyl group bridged by the nitrogen to the 2C-C core. The aryl benzyl moiety has been shown to increase affinity and selectivity for the 5-HT2A receptor in the non-chlorinated 2C-H phenethylamine series3 . Moreover, the 3,4,5 tri-methoxy benzyl group resembles the hallucinogenic alkaloid mescaline, less one carbon in the alkyl chain. The physiological and toxicological properties of this compound are not known.
  3. 1 2 3 Åstrand A, Guerrieri D, Vikingsson S, Kronstrand R, Green H (December 2020). "In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT1A, and 5-HT2A receptors-On-target receptor potency and efficacy, and off-target effects". Forensic Science International. 317 110553. doi:10.1016/j.forsciint.2020.110553. PMID 33160102. The three compounds of the NBOMe series with the lowest potency were 25I-NBOMe, 25T4-NBOMe and C30- NBOMe. 25I-NBOMe and 25T4-NBOMe presented EC50-values one order of magnitude lower than LSD (Table 3B) while the EC50 of C30-NBOMe was orders of magnitude higher (1251 nM, 95 % CI 653–2581 nM).
  4. 1 2 "EMCDDA–Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA". Isomerdesign.com. Retrieved 12 June 2026.
  5. ↑ Wang S, Zhu A, Paudel S, Jang CG, Lee YS, Kim KM (March 2023). "Structure-Activity Relationship and Evaluation of Phenethylamine and Tryptamine Derivatives for Affinity towards 5-Hydroxytryptamine Type 2A Receptor". Biomolecules & Therapeutics. 31 (2): 176–182. doi:10.4062/biomolther.2022.096. PMC 9970836. PMID 36224112.
  6. ↑ Lum BJ, Brophy JJ, Hibbert DB (2 January 2016). "Identification of 4-substituted 2-(4-x-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25X-NBOMe) and analogues by gas chromatography–mass spectrometry analysis of heptafluorobutyric anhydride (HFBA) derivatives". Australian Journal of Forensic Sciences. 48 (1): 59–73. doi:10.1080/00450618.2015.1026274. ISSN 0045-0618.
  7. ↑ Clancy L, Philp M, Shimmon R, Fu S (May 2021). "Development and validation of a color spot test method for the presumptive detection of 25-NBOMe compounds". Drug Testing and Analysis. 13 (5): 929–943. doi:10.1002/dta.2905. PMID 32744773.
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