25I-NBOH

25I-NBOH
Systematic (IUPAC) name
	2-((2-(4-iodo-2,5-dimethoxyphenyl)ethylamino)methyl)phenol
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	919797-20-9
ATC code	?
PubChem	CID 10001761
ChemSpider	8177342
Chemical data
Formula	C17H20INO3
Mol. mass	413.249 g/mol
	SMILES Oc2ccccc2CNCCc(c(OC)cc1I)cc1OC;
	InChI InChI=1S/C17H20INO3/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:FEUZHYRXGQTBRO-UHFFFAOYSA-N ;
(what is this?) (verify);

25I-NBOH (NBOH-2CI, Cimbi-27) is a derivative of the phenethylamine derived hallucinogen 2C-I. It acts as a potent agonist for the 5HT_2A receptor,^[1]^[2] with a Ki of 0.061nM at the human 5HT_2A receptor, making it some twelve times the potency of 2C-I itself. In vitro tests showed this compound acted as an agonist but animal studies have not been reported. While the N-benzyl derivatives of 2C-I were significantly increased in potency compared to 2C-I, the N-benzyl derivatives of DOI were inactive.^[3]

It was discovered in 2006 by a team at Purdue University.

[edit] See also

2CBCB-NBOMe (NBOMe-TCB-2)
2CBFly-NBOMe (NBOMe-2CB-Fly)
25B-NBOMe (NBOMe-2CB)
2C-C-NBOMe (NBOMe-2CC)
25I-NBMD (NBMD-2CI)
25I-NBOMe (NBOMe-2CI)
2C-TFM-NBOMe (NBOMe-2C-TFM)
25I-NBF (NBF-2CI)

[edit] References

^ Ettrup, A. E. A. ; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M. et al. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging 38 (4): 681–693. doi:10.1007/s00259-010-1686-8. ISBN 0025901016868. PMID 21174090. |displayauthors= suggested (help) edit
^ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor". Journal of Computer-aided Molecular Design 25 (1): 51–66. doi:10.1007/s10822-010-9400-2. PMID 21088982.
^ Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE (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.

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[1] Ettrup, A. E. A. ; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M. et al. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging 38 (4): 681–693. doi:10.1007/s00259-010-1686-8. ISBN 0025901016868. PMID 21174090. |displayauthors= suggested (help) edit

[pmid21088982-2] Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor". Journal of Computer-aided Molecular Design 25 (1): 51–66. doi:10.1007/s10822-010-9400-2. PMID 21088982.

[3] Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE (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.

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[2]

[3]

25I-NBOH

[edit] See also

[edit] References

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