25B-NBOMe

25B-NBOMe
Clinical data
Other names	NBOMe-2C-B; Cimbi-36; Nova; BOM 2-CB; N-(2-Methoxybenzyl)-4-bromo-2,5-dimethoxyphenethylamine
Routes of; administration	Sublingual, others
Drug class	Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
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, also known as NBOMe-2C-B and Cimbi-36, is a psychedelic drug of the 25-NB (NBOMe) family derived from 2C-B. It acts as a potent full agonist for the 5HT_2A receptor. Duration of effects lasts about 3 to 10 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.

25B-NBOMe was first described in the scientific literature by Ralf Heim and colleagues at the Free University of Berlin by 1999.

Clinical data

Other names	NBOMe-2C-B; Cimbi-36; Nova; BOM 2-CB; N-(2-Methoxybenzyl)-4-bromo-2,5-dimethoxyphenethylamine
Routes of administration	Sublingual, others
Drug class	Serotonin 5-HT₂ receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
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^Y
PubChem CID	9977044
ChemSpider	8152636^Y
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^Y Key:SUXGNJVVBGJEFB-UHFFFAOYSA-N^Y
(verify)