25C-NBOH

{{Infobox drug

| Verifiedfields =

| verifiedrevid =

| IUPAC_name = 2-({[2-(4-chloro-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol

| image = NBOH-2CC_structure.png

| tradename =

| legal_BR = F2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

| legal_DE = NpSG

| legal_UK = Class A

| CAS_number = 1391488-16-6

| CAS_number_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = P8BP3X5EBR

| PubChem = 125181419

| ChemSpiderID_Ref =

| ChemSpiderID = 58191432

| C=17 | H=20 | Cl=1 | N=1 | O=3

| smiles = COc1cc(Cl)c(OC)cc1CCNCc2ccccc2O

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = VHWXICYYQMMZCW-UHFFFAOYSA-N

}}

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.{{cite journal | vauthors = Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL | title = Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists | journal = ACS Chemical Neuroscience | volume = 5 | issue = 3 | pages = 243–9 | date = March 2014 | pmid = 24397362 | pmc = 3963123 | doi = 10.1021/cn400216u }}{{cite thesis | vauthors = Hansen M | title = Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. | degree = Ph.D. | publisher = University of Copenhagen | date = 2010-12-16 | doi = 10.13140/RG.2.2.33671.14245}}

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.{{cite journal | vauthors = Arantes LC, Júnior EF, de Souza LF, Cardoso AC, Alcântara TL, Lião LM, Machado Y, Lordeiro RA, Neto JC, Andrade AF | display-authors = 6 | title = 2A receptor agonist identified in blotter paper seizures in Brazil | journal = Forensic Toxicology | volume = 35 | issue = 2 | pages = 408–414 | year = 2017 | pmid = 28706567 | pmc = 5486617 | doi = 10.1007/s11419-017-0357-x }}{{cite journal | vauthors = Machado Y, Lordeiro RA, Neto JC, Alves RB, Piccin E | title = Identification of new NBOH drugs in seized blotter papers: 25B-NBOH, 25C-NBOH, and 25E-NBOH | journal = Forensic Toxicology | volume = 38 | issue = 2 | pages = 203–215 | year = 2019 | doi = 10.1007/s11419-019-00509-7 | s2cid = 209672508 | doi-access = free }} An alternative method proposed for reliable identification of 25I-NBOH using GC/MS may be used for 25C-NBOH analysis.{{cite journal | vauthors = Neto JC, Andrade AF, Lordeiro RA, Machado Y, Elie M, Júnior EF, Arantes LC | title = Preventing misidentification of 25I-NBOH as 2C-I on routine GC–MS analyses| journal = Forensic Toxicology| volume = 35| issue = 2| pages = 415–420| year = 2017 | doi = 10.1007/s11419-017-0362-0 | s2cid = 32432586| url = http://eprints.lincoln.ac.uk/26957/7/25i-nboh%20aceito.pdf}}{{cite journal | vauthors = Machado Y, Lordeiro RA, Neto JC, Alves RB, Piccin E | title = Identification of new NBOH drugs in seized blotter papers: 25B-NBOH, 25C-NBOH, and 25E-NBOH | journal = Forensic Toxicology | volume = 38 | issue = 2 | pages = 203–215 | year = 2019 | doi = 10.1007/s11419-019-00509-7 | s2cid = 209672508 | doi-access = free }}

Legality

=United Kingdom=

References

Category:25-NB (psychedelics)

Category:Chlorobenzene derivatives

Category:Designer drugs

Category:Serotonin receptor agonists