25C-NBOH

25-C-NBOH (2C-C-NBOH, NBOH-2CC) is a derivative of the phenethylamine derived hallucinogen 2C-C which has been sold as a designer drug. It has similar serotonin receptor affinity to the better-known compound 25C-NBOMe.[1][2]

25C-NBOH
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
IUPAC name
  • 2-({[2-(4-chloro-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC17H20ClNO3
Molar mass321.80 g·mol−1
3D model (JSmol)
SMILES
  • COc1cc(Cl)c(OC)cc1CCNCc2ccccc2O
InChI
  • InChI=1S/C17H20ClNO3/c1-21-16-10-14(18)17(22-2)9-12(16)7-8-19-11-13-5-3-4-6-15(13)20/h3-6,9-10,19-20H,7-8,11H2,1-2H3
  • Key:VHWXICYYQMMZCW-UHFFFAOYSA-N

Analogues and derivatives

Analytical chemistry

25C-NBOH undergoes degradation under routine Gas Chromatography (GC) conditions, as well as other NBOH's substances, into 2C-C.[3][4] An alternative method proposed for reliable identification of 25I-NBOH using GC/MS may be used for 25C-NBOH analysis.[5][6]

Legality

United Kingdom

This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.[7]

References
  1. Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (March 2014). "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience. 5 (3): 243–9. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.
  2. Hansen M (2010-12-16). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (Ph.D. thesis). University of Copenhagen. doi:10.13140/RG.2.2.33671.14245.
  3. Arantes LC, Júnior EF, de Souza LF, Cardoso AC, Alcântara TL, Lião LM, et al. (2017). "2A receptor agonist identified in blotter paper seizures in Brazil". Forensic Toxicology. 35 (2): 408–414. doi:10.1007/s11419-017-0357-x. PMC 5486617. PMID 28706567.
  4. Machado Y, Lordeiro RA, Neto JC, Alves RB, Piccin E (2019). "Identification of new NBOH drugs in seized blotter papers: 25B-NBOH, 25C-NBOH, and 25E-NBOH". Forensic Toxicology. 38 (2): 203–215. doi:10.1007/s11419-019-00509-7.
  5. Neto JC, Andrade AF, Lordeiro RA, Machado Y, Elie M, Júnior EF, Arantes LC (2017). "Preventing misidentification of 25I-NBOH as 2C-I on routine GC–MS analyses" (PDF). Forensic Toxicology. 35 (2): 415–420. doi:10.1007/s11419-017-0362-0. S2CID 32432586.
  6. Machado Y, Lordeiro RA, Neto JC, Alves RB, Piccin E (2019). "Identification of new NBOH drugs in seized blotter papers: 25B-NBOH, 25C-NBOH, and 25E-NBOH". Forensic Toxicology. 38 (2): 203–215. doi:10.1007/s11419-019-00509-7.
  7. "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
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