25I-NBMD

25I-NBMD
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Class A;
Identifiers
	IUPAC name N-[(2H-1,3-benzodioxol-4-yl)methyl]-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine;
CAS Number	919797-25-4 ;
PubChem CID	57507899;
ChemSpider	26234932 ;
UNII	R99110126K;
CompTox Dashboard (EPA)	DTXSID70726967 ;
Chemical and physical data
Formula	C18H20INO4
Molar mass	441.265 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 ;
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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 0.049 nM 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]

^ 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.
^ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.
^ 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.
^ Isberg V, Balle T, Sander T, Jørgensen FS, Gloriam DE (February 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.

[1] 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.

[2] Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.

[3] 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.

[pmid21261291-4] Isberg V, Balle T, Sander T, Jørgensen FS, Gloriam DE (February 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.

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