25I-NBOMe

25I-NBOMe (2C-I-NBOMe, Cimbi-5, Smiles and also shortened to "25I") is a novel synthetic psychoactive substance with strong hallucinogenic properties, synthesized in 2003 for research purposes. Since 2010, it has circulated in the recreational drug scene, often misrepresented as LSD. The recreational usage of 25I is associated with severe intoxication and deaths in humans.

25I-NBOMe
Clinical data
Routes of
administration		Buccal (sublabial), sublingual, insufflated, inhalation, intravenous, intramuscular, rectal
ATC code
  • none
Legal status
Legal status
Identifiers
  • 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H22INO3
Molar mass427.282 g·mol−1
3D model (JSmol)
SMILES
  • COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)I)OC
  • 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?)  (verify)
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25I was synthesized for biochemistry research to map the brain's usage of the type 2A serotonin receptor. A derivative of the substituted phenethylamine 2C-I family, it is the most well-known member of the 25-NB family. 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-HT2A receptor full agonist PET radioligand, [11C]CIMBI-5 shows promise as a more functional marker of these receptors, particularly in their high affinity states.

Street and media nicknames for this drug are: "N-Bomb", "Solaris", "Smiles", and "Wizard", although the drug is frequently fraudulently sold as LSD.

Due to its physical effects and risk of overdose, there have been multiple deaths attributed to the drug. Its long term toxicity is unknown due to lack of existing research.

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