25B-NBOH
- 2-({[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol
- 1335331-46-8 Y
- 125181394
- 58191433
- KHR1SJ9L0Y
- DTXSID401017175
- Interactive image
- BrC2=CC(=C(CCNCC1=C(C=CC=C1)O)C=C2OC)OC
- InChI=1S/C17H20BrNO3/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:RSUNJYKZRKIBNB-UHFFFAOYSA-N
25B-NBOH (2C-B-NBOH, NBOH-2C-B) is a derivative of the phenethylamine derived hallucinogen 2C-B which has been sold as a designer drug. It acts as a potent serotonin receptor agonist with similar affinity to the better-known compound 25B-NBOMe at 5-HT2A and 5-HT2C receptors with pKis[clarification needed] values of 8.3 and 9.4, respectively.[2][3][4][5][6][7]
Legal status
Sweden
The Riksdag added 25B-NBOH to Narcotic Drugs Punishments Act under Swedish Schedule I ("substances, plant materials and fungi which normally do not have medical use") as of January 26, 2016, published by Medical Products Agency (MPA) in regulation HSLF-FS 2015:35 listed as 25B-NBOH, and 2-([2-(4-bromo-2,5-dimetoxifenyl)etylamino]metyl)fenol.[8]
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.[9]
Analogues and derivatives
Analogues and derivatives of 2C-B:
25-N:
- 25B-N1POMe
- 25B-NAcPip
25-NM:
- 25B-NMe7BF
- 25B-NMe7BT
- 25B-NMe7Bim
- 25B-NMe7Box
- 25B-NMe7DHBF
- 25B-NMe7Ind
- 25B-NMe7Indz
- 25B-NMePyr
- 2C-B-FLY
- 2CBFly-NBOMe (NBOMe-2CB-Fly)
- DOB-FLY
- DOB-2-DRAGONFLY-5-BUTTERFLY
N-(2C)-fentanyl:
Other:
- BOB
- BOH-2C-B, β-Hydroxy-2C-B, βOH-2CB[12][13]
- BMB
- 2C-B-5-hemifly
- 2C-B-aminorex (2C-B-AR)
- 2C-B-AN
- 2C-B-BZP
- 2C-B-FLY-NB2EtO5Cl
- 2C-B-PP
- 2CB-Ind
- βk-2C-B (beta-keto 2C-B)
- N-Ethyl-2C-B
- TCB-2 (2C-BCB)
References
- ^ 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.
- ^ Heim R (19 March 2004). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur (Ph.D. thesis). Freie Universität Berlin. Archived from the original on 16 April 2012. Retrieved 27 June 2015.
- ^ 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.
- ^ Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, et al. (April 2011). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–93. doi:10.1007/s00259-010-1686-8. PMID 21174090. S2CID 12467684.
- ^ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. Bibcode:2011JCAMD..25...51S. CiteSeerX 10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982. S2CID 3103050.
- ^ Braden MR, Parrish JC, Naylor JC, Nichols DE (December 2006). "Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists". Molecular Pharmacology. 70 (6): 1956–64. doi:10.1124/mol.106.028720. PMID 17000863. S2CID 15840304.
- ^ "Läkemedelsverkets föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotik" [The Swedish Medicines Agency's regulations on amendments to the Swedish Medicines Agency's regulations (LVFS 2011: 10) on lists of drugs] (PDF). Läkemedelsverket.
- ^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
- ^ "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.
- ^ "Explore N-(2C-FLY)-Fentanyl | PiHKAL · info". isomerdesign.com.
- ^ Glennon, Richard A.; Bondarev, Mikhail L.; Khorana, Nantaka; Young, Richard; May, Jesse A.; Hellberg, Mark R.; McLaughlin, Marsha A.; Sharif, Najam A. (November 2004). "β-Oxygenated Analogues of the 5-HT2ASerotonin Receptor Agonist 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–6041. doi:10.1021/jm040082s. ISSN 0022-2623. PMID 15537358.
- ^ Beta-hydroxyphenylalkylamines and their use for treating glaucoma
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(5-HT2A
agonists)
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(NMDAR
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antagonists)
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