25B-NBOMe

25B-NBOMe
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Identifiers
	IUPAC name 2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine;
CAS Number	1026511-90-9 ;
PubChem CID	9977044;
ChemSpider	8152636 ;
UNII	S6NAA81PHK;
KEGG	C22773;
CompTox Dashboard (EPA)	DTXSID50907974 ;
Chemical and physical data
Formula	C18H22BrNO3
Molar mass	380.282 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)Br)OC;
	InChI InChI=1S/C18H22BrNO3/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 ; Key:SUXGNJVVBGJEFB-UHFFFAOYSA-N ;
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25B-NBOMe (NBOMe-2C-B, Cimbi-36, Nova, BOM 2-CB) is a derivative of the phenethylamine psychedelic 2C-B, discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent full agonist for the 5HT_2A receptor. Anecdotal reports from users suggest 25B-NBOMe to be an active hallucinogen at a dose of as little as 250–500 μg, making it a similar potency to other phenethylamine derived hallucinogens such as Bromo-DragonFLY. Duration of effects lasts about 12–16 hours, although the parent compound is rapidly cleared from the blood when used in the radiolabeled form in tracer doses. Recently, Custodio et al. (2019) evaluated the potential involvement of dysregulated dopaminergic system, neuroadaptation, and brain wave changes which may contribute to the rewarding and reinforcing properties of 25B-NBOMe in rodents.

The carbon-11 labeled version of this compound ([¹¹C]Cimbi-36) was synthesized and validated as a radioactive tracer for positron emission tomography (PET) in Copenhagen. As a 5-HT_2A receptor agonist PET radioligand, [¹¹C]Cimbi-36 was hypothesized to provide a more functional marker of these receptors. Also, [¹¹C]Cimbi-36 is investigated as a potential marker of serotonin release and thus could serve as an indicator of serotonin levels in vivo. [¹¹C]Cimbi-36 is now undergoing clinical trials as a PET-ligand in humans.

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