Chemistry:C30-NBOMe

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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 (EC50 = 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

  • 25-NB (psychedelics)

References

  1. ↑ 1.0 1.1 1.2 "New Psychoactive Substances: Major Groups, Laboratory Testing Challenges, Public Health Concerns, and Community-Based Solutions". Journal of Chemistry 2023: 1–36. 2 February 2023. doi:10.1155/2023/5852315. ISSN 2090-9071. 
  2. ↑ 2.0 2.1 2.2 "Analytical Profile of 30C-NBOMe", Forensic Drug Review (Cayman Chemical Company), 13 November 2015, https://isomerdesign.com/bitnest/fdr/30C-NBOMe.pdf, "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. ↑ 3.0 3.1 3.2 "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. December 2020. 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. ↑ 4.0 4.1 https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2013
  5. ↑ "Structure-Activity Relationship and Evaluation of Phenethylamine and Tryptamine Derivatives for Affinity towards 5-Hydroxytryptamine Type 2A Receptor". Biomolecules & Therapeutics 31 (2): 176–182. March 2023. doi:10.4062/biomolther.2022.096. PMID 36224112. 
  6. ↑ "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. 2 January 2016. doi:10.1080/00450618.2015.1026274. ISSN 0045-0618. 
  7. ↑ "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. May 2021. doi:10.1002/dta.2905. PMID 32744773. 



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