25C-NBOH

25C-NBOH
Clinical data
Other names	2C-C-NBOH; NBOH-2CC
Routes of; administration	Sublingual
Drug class	Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); DE: NpSG (Industrial and scientific use only); UK: Class A;
Pharmacokinetic data
Onset of action	Up to 45 minutes
Identifiers
	IUPAC name 2-({[2-(4-chloro-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol;
CAS Number	1391488-16-6 ;
PubChem CID	125181419;
ChemSpider	58191432;
UNII	P8BP3X5EBR;
Chemical and physical data
Formula	C17H20ClNO3
Molar mass	321.80 g·mol−1
3D model (JSmol)	Interactive image;
	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;

25C-NBOH (2C-C-NBOH, NBOH-2CC) is a psychedelic drug and derivative of the phenethylamine derived hallucinogen 2C-C. It has similar serotonin receptor affinity to the better-known compound 25C-NBOMe.^[3]^[4] The drug has been encountered as a novel designer drug.^[1]

Use and effects

25C-NBOH is said to have a dose of 100 to 750 μg sublingually and an onset of up to 45 minutes.^[1]

Interactions

Chemistry

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.^[5]^[6] An alternative method proposed for reliable identification of 25I-NBOH using GC/MS may be used for 25C-NBOH analysis.^[7]^[8]

Society and culture

Legal status

Canada

25C-NBOH is a controlled substance in Canada under phenethylamine blanket-ban language.^[9]

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.^[10]

References

1 2 3 4 "25C-NBOH". АИПСИН (in Russian). Retrieved 2 January 2026.
↑ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
↑ 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.
↑ 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.
↑ 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.
↑ 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. S2CID 209672508.
↑ 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.
↑ 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. S2CID 209672508.
↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.

External links

[Aipsin-1] 1 2 3 4 "25C-NBOH". АИПСИН (in Russian). Retrieved 2 January 2026.

[2] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[3] 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.

[4] 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.

[5] 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.

[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. S2CID 209672508.

[7] 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.

[8] 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. S2CID 209672508.

[CDSA-9] "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

[10] "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.

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