25I-NBOMe

25I-NBOMe

Clinical data
Routes of administration	Buccal (sublabial), sublingual, insufflated, inhalation, intravenous, intramuscular, rectal
ATC code	none
Legal status
Legal status	DE: Anlage I (Controlled) UK: Class A US: Schedule I
Identifiers
IUPAC name 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number	919797-19-6 N
PubChem CID	10251906
ChemSpider	8427392 Y
UNII	547KGL06IP
ChEMBL	CHEMBL1908863 N
Chemical and physical data
Formula	C18H22INO3
Molar mass	427.28 g/mol
3D model (Jmol)	Interactive image
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 Y Key:ZFUOLNAKPBFDIJ-UHFFFAOYSA-N Y
NY (what is this?)

25I-NBOMe (2C-I-NBOMe, Cimbi-5, also shortened to "25I", and colloquially referred to as "N-bomb") is a psychedelic drug and derivative of the substituted phenethylamine psychedelic 2C-I. It was discovered in 2003 by chemist Ralf Heim at the Free University of Berlin, who published his findings in his PhD dissertation. The compound was subsequently investigated by a team at Purdue University led by David Nichols.

The carbon-11 labelled version of 25I-NBOMe, ^[11C]Cimbi-5, was synthesized and validated as a radiotracer for positron emission tomography (PET) in Copenhagen. Being the first 5-HT_2A receptor full agonist PET radioligand, ^[11C]-CIMBI-5 shows promise as a more functional marker of these receptors, particularly in their high affinity states.

Like other 2C-X-NBOMe molecules, 25I-NBOMe is a derivative of the 2C family of phenethylamines described by Alexander Shulgin in his book PiHKAL. Specifically, 25I-NBOMe is an N-benzyl derivative of the phenethylamine molecule 2C-I, formed by adding a 2-methoxybenzyl (BnOMe) onto the nitrogen (N) of the phenethylamine backbone. This substitution significantly increases the potency of the molecule.

25I-NBOMe can be synthesised from 2C-I and 2-methoxybenzaldehyde, via reductive alkylation. It can be done stepwise by first making the imine and then reducing the formed imine with sodium borohydride, or by direct reaction with sodium triacetoxyborohydride.

25I-NBOMe acts as a highly potent full agonist for the human 5-HT_2A receptor, with a K_i of 0.044 nM, making it some sixteen times the potency of 2C-I itself at this receptor. A radiolabelled form of 25I-NBOMe can be used for mapping the distribution of 5-HT_2A receptors in the brain.