25I-NBMD: Difference between revisions

{{Short description|Chemical compound}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 452164662

| IUPAC_name = ''N''-[(2''H''-1,3-benzodioxol-4-yl)methyl]-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine

| image = 25I-NBMD.svg

| legal_DE = NpSG

| legal_UK = Class A

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 919797-25-4

| PubChem = 57507899

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 26234932

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = R99110126K

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NJNMIPDEUMTYNV-UHFFFAOYSA-N

| C=18 | H=20 | I=1 | N=1 | O=4

'''25I-NBMD''' ('''NBMD-2C-I''', '''Cimbi-29''') is a derivative of the [[phenethylamine]] [[Psychedelic drug|hallucinogen]] [[2C-I]], discovered in 2006 by a team at [[Purdue University]] led by [[David E. Nichols|David Nichols]]. It acts as a potent [[partial agonist]] for the [[5HT2A receptor|5HT_2A]] [[Receptor (biochemistry)|receptor]] with a [[Dissociation constant|Ki]] of 0.049 nM at the human 5HT_2A receptor.<ref>{{cite journal | vauthors = Braden MR, Parrish JC, Naylor JC, Nichols DE | title = Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists | journal = Molecular Pharmacology | volume = 70 | issue = 6 | pages = 1956–64 | date = December 2006 | pmid = 17000863 | doi = 10.1124/mol.106.028720 | s2cid = 15840304 }}</ref><ref>{{cite thesis | url = https://www.proquest.com/docview/304838368 | first = Michael Robert | last = Braden | name-list-style = vanc | degree = Ph.D. | title = Towards a biophysical understanding of hallucinogen action. | publisher = Purdue University | date = 2007 | id = {{ProQuest|304838368}} }}</ref><ref>{{cite journal | vauthors = Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM | display-authors = 6 | title = Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers | journal = European Journal of Nuclear Medicine and Molecular Imaging | volume = 38 | issue = 4 | pages = 681–93 | date = April 2011 | pmid = 21174090 | doi = 10.1007/s00259-010-1686-8 | s2cid = 12467684 }}</ref> The corresponding 4-bromo analogue 25B-NBMD has been used for molecular dynamics studies on the shape of the 5-HT_2A receptor.<ref name="pmid21261291">{{cite journal | vauthors = Isberg V, Balle T, Sander T, Jørgensen FS, Gloriam DE | title = G protein- and agonist-bound serotonin 5-HT2A receptor model activated by steered molecular dynamics simulations | journal = Journal of Chemical Information and Modeling | volume = 51 | issue = 2 | pages = 315–25 | date = February 2011 | pmid = 21261291 | doi = 10.1021/ci100402f }}</ref>

==Legality==

===Sweden===

[[Riksdag|The Riksdag]] added 25I-NBMD to [[:sv:Narkotikastrafflagen|Narcotic Drugs Punishments Act]] under ''swedish schedule I'' (''"substances, plant materials and fungi which normally do not have medical use"'') as of January 16, 2015, published by [[Medical Products Agency (Sweden)|Medical Products Agency (MPA)]] in regulation ''LVFS 2014:11'' listed as '''25I-NBMD''', and '''2-(4-jodo-2,5-dimetoxifenyl)-N-[(2,3-metylendioxifenyl)metyl]etanamin'''.<ref>{{Cite web |url=https://lakemedelsverket.se/upload/lvfs/LVFS_2014_11.pdf |title=Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika |trans-title=Regulations amending the Medical Products Agency's regulations (LVFS 2011:10) on lists of narcotics|lang=sv|access-date=2017-04-21 |archive-url=https://web.archive.org/web/20150316055728/http://www.lakemedelsverket.se/upload/lvfs/LVFS_2014_11.pdf |archive-date=2015-03-16 |url-status=dead }}</ref>

===United Kingdom===

{{N-benzylphenethylamine-Legality-United Kingdom}}

==Analogues and derivatives==

{{2C-I analogues and derivatives}}

== References ==

{{Hallucinogens}}

{{Serotonin receptor modulators}}

{{Phenethylamines}}

[[Category:25-NB (psychedelics)]]

[[Category:Designer drugs]]

[[Category:Iodobenzene derivatives]]

[[Category:Serotonin receptor agonists]]