25I-NBMD

25I-NBMD
Systematic (IUPAC) name
	2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2,3-methylenedioxyphenyl)methyl]ethanamine
Identifiers
CAS Number	919797-25-4
ChemSpider	26234932
UNII	R99110126K
Chemical data
Formula	C18H20INO4
Molar mass	441.259 g/mol
	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 0.049nM 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 µg and 1.5 mg. Although the low end of the dose response curve is similar to LSD, being active at 500 µg, 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. As a recreational drug, 25I-NBMD has not been on the open market for long; therefore there are very few reports about its use.

Legality[edit]

Sweden's public health agency suggested to classify 25I-NBMD as hazardous substance on November 10, 2014.^[5]

References[edit]

^ 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.
^ Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J.; et al. (2010). "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.
^ 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.
^ "Cannabinoider föreslås bli klassade som hälsofarlig vara". Retrieved 29 June 2015.

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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] Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J.; et al. (2010). "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.

[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.

[5] "Cannabinoider föreslås bli klassade som hälsofarlig vara". Retrieved 29 June 2015.

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25I-NBMD

Legality[edit]

See also[edit]

References[edit]

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