25I-NBOMe

25I-NBOMe
IUPAC ime
	2-(4-jodo-2,5-dimetoksifenil)-N-[(2-metoksifenil)metil]etanamin
Klinički podaci
Način primene	Sublingualno, potkožno, intravenozno, intramuskularno, rektalno
Identifikatori
CAS broj	919797-19-6 ; 1043868-97-8 (hidrohlorid)
ATC kod	none
PubChem	CID 10251906
ChemSpider	8427392
Hemijski podaci
Formula	C18H22INO3
Molarna masa	427,2784 g/mol
	SMILES COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)I)OC; ;
	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 ;

25I-NBOMe (2C-I-NBOMe) je derivat fenetilaminskog psihodelika 2C-I.^[1]^[2]

25I-NBOMe deluje kao visoko potentan pun agonist ljudskog 5-HT_2A receptora,^[3]^[4] 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.^[5] 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.^[6]

Reference

^ „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. Приступљено 8. 8. 2012.
^ „Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007”. Proquest.umi.com. Приступљено 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. PMID 21174090. doi:10.1007/s00259-010-1686-8. ISBN 0-02-590101686-8.
^ Silva ME, Heim R, Strasser A, Elz S, Dove S (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. PMID 21088982. doi:10.1007/s10822-010-9400-2.
^ Nichols DE, Frescas SP, Chemel BR, Rehder KS, Zhong D, Lewin AH (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. PMC 2719953 . PMID 18468904. doi:10.1016/j.bmc.2008.04.050.
^ 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. PMID 17000863. doi:10.1124/mol.106.028720.

Vidi još

2CBCB-NBOMe (NBOMe-TCB-2)
2CBFly-NBOMe (NBOMe-2CB-Fly)
25C-NBOMe (NBOMe-2CC)
25B-NBOMe (NBOMe-2CB)
25I-NBMD (NBMD-2CI)
25I-NBOH (NBOH-2CI)
25I-NBF (NBF-2CI)
5-MeO-NBpBrT

Spoljašnje veze

INBMeO

[1] „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. Приступљено 8. 8. 2012.

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

[3] 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. PMID 21174090. doi:10.1007/s00259-010-1686-8. ISBN 0-02-590101686-8.

[pmid21088982-4] Silva ME, Heim R, Strasser A, Elz S, Dove S (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. PMID 21088982. doi:10.1007/s10822-010-9400-2.

[pmid18468904-5] Nichols DE, Frescas SP, Chemel BR, Rehder KS, Zhong D, Lewin AH (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. PMC 2719953 . PMID 18468904. doi:10.1016/j.bmc.2008.04.050.

[6] 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. PMID 17000863. doi:10.1124/mol.106.028720.

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