25I-NBOMe

25I-NBOMe
(IUPAC) ime
	2-(4-jodo-2,5-dimetoksifenil)-N-[(2-metoksifenil)metil]etanamin
Klinički podaci
Identifikatori
CAS broj	919797-19-6 ; 1043868-97-8 (hidrohlorid)
ATC kod	nije dodeljen
PubChem	10251906
ChemSpider	8427392
Hemijski podaci
Formula	C18H22INO3
Mol. masa	427,2784 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C18H22INO3/c1-21-16-7-5-4-6-14(16)12-20-9-8-13-10-18(23-3)15(19)11-17(13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3 ; Key: ZFUOLNAKPBFDIJ-UHFFFAOYSA-N
Farmakoinformacioni podaci
Trudnoća	?
Pravni status
Način primene	Sublingualno, potkožno, intravenozno, intramuskularno, rektalno

25I-NBOMe (2C-I-NBOMe) je derivat fenetilaminskog psihodelika 2C-I.^[4]^[5]

25I-NBOMe deluje kao visoko potentan pun agonist ljudskog 5-HT_2A receptora,^[6]^[7] sa K_i od 0,044 nM, te je šesnaest puta potentniji od 2C-I liganda. Radio obeležena forma 25I-NBOMe se može koristiti za mapiranje distribucije 5-HT_2A receptora u mozgu.^[8] In vitro testovi su pokazali da ovo jedinjenje deluje kao agonist, ali rezultati životinjskih studija nisu objavljeni. Dok N-benzilni derivati 2C-I znatno povećavaju potentnost, N-benzilni derivati 2,5-dimetoksi-4-jodoamfetamina su neaktivni.^[9]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ „Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)”. Diss.fu-berlin.de. 28. 2. 2010.. Pristupljeno 8. 8. 2012.
↑ „Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007”. Proquest.umi.com. Pristupljeno 8. 8. 2012.
↑ Ettrup, A. 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. PMID 21174090.
↑ 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.
↑ Nichols DE, Frescas SP, Chemel BR, Rehder KS, Zhong D, Lewin AH (June 2008). „High Specific Activity Tritium-Labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): A High Affinity 5-HT2A Receptor-Selective Agonist Radioligand”. Bioorganic & Medicinal Chemistry 16 (11): 6116–23. DOI:10.1016/j.bmc.2008.04.050. PMC 2719953. PMID 18468904.
↑ 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.

Povezano

Spoljašnje veze

	Portal Medicina
	Portal Hemija

INBMeO

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] „Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)”. Diss.fu-berlin.de. 28. 2. 2010.. Pristupljeno 8. 8. 2012.

[5] „Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007”. Proquest.umi.com. Pristupljeno 8. 8. 2012.

[6] Ettrup, A. 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. PMID 21174090.

[pmid21088982-7] 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.

[pmid18468904-8] Nichols DE, Frescas SP, Chemel BR, Rehder KS, Zhong D, Lewin AH (June 2008). „High Specific Activity Tritium-Labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): A High Affinity 5-HT2A Receptor-Selective Agonist Radioligand”. Bioorganic & Medicinal Chemistry 16 (11): 6116–23. DOI:10.1016/j.bmc.2008.04.050. PMC 2719953. PMID 18468904.

[9] 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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