25I-NBMD

25I-NBMD
Identifiers
	IUPAC name 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2,3-methylenedioxyphenyl)methyl]ethanamine;
CAS Number	919797-25-4 ;
ChemSpider	26234932 ;
CompTox Dashboard (EPA)	DTXSID70726967 ;
Chemical and physical data
Formula	C18H20INO4
Molar mass	441.259 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c13OCOc3cccc1CNCCc(c(OC)cc2I)cc2OC;
	InChI InChI=1S/C18H20INO4/c1-21-16-9-14(19)17(22-2)8-12(16)6-7-20-10-13-4-3-5-15-18(13)24-11-23-15/h3-5,8-9,20H,6-7,10-11H2,1-2H3 ; Key:NJNMIPDEUMTYNV-UHFFFAOYSA-N ;
	(verify)

25I-NBMD (NBMD-2C-I, Cimbi-29) is a derivative of the phenethylamine hallucinogen 2C-I, discovered in 2006 by a team at Purdue University led by David Nichols. It acts as a potent partial agonist for the 5HT_2A receptor with a Ki of 0.049nM at the human 5HT_2A receptor.^[1]^[2]^[3] The corresponding 4-bromo analogue 25B-NBMD has been used for molecular dynamics studies on the shape of the 5-HT_2A receptor.^[4] Common doses are reported to be between 500 Mcg and 1.5 mg. Although the low end of the dose response curve is similar to LSD, being active at 500 Mcg, some reports show 1.5–2.0 mg being a low dose, making it up to four times less active than its nbome counterpart 25I-NBOMe. Because it is a research chemical and has not been on the open market for long, there are very few reports about its use.

References

^ 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.
^ Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.
^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1007/s00259-010-1686-8, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1007/s00259-010-1686-8 instead.
^ Isberg V, Balle T, Sander T, Jørgensen FS, Gloriam DE (2011). "G protein- and agonist-bound serotonin 5-HT2A receptor model activated by steered molecular dynamics simulations". Journal of Chemical Information and Modeling. 51 (2): 315–25. doi:10.1021/ci100402f. PMID 21261291. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

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[1] 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.

[2] Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.

[3] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1007/s00259-010-1686-8, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1007/s00259-010-1686-8 instead.

[pmid21261291-4] Isberg V, Balle T, Sander T, Jørgensen FS, Gloriam DE (2011). "G protein- and agonist-bound serotonin 5-HT2A receptor model activated by steered molecular dynamics simulations". Journal of Chemical Information and Modeling. 51 (2): 315–25. doi:10.1021/ci100402f. PMID 21261291. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

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See also

References