2C-B-morpholine

2C-B-morpholine, also known as 2C-B-norphenmetrazine or as 2-(4-bromo-2,5-dimethoxyphenyl)morpholine, is a serotonin receptor modulator of the phenylmorpholine (phenmetrazine) and cyclized phenethylamine groups.^[1] It is a ligand of the serotonin 5-HT_2A receptor, with an affinity of 20.6 nM and an E_maxTooltip maximal efficacy of 4%.^[1] The drug showed 103-fold lower affinity for this receptor than R(–)-DOB and had minimal agonist activity (with R(–)-DOB having an E_max of 51% in the assay), so for practical purposes would act as an antagonist at the 5-HT_2A receptor under most circumstances, despite being technically classified as a partial agonist.^[1] 2C-B-morpholine was first described in the scientific literature by Richard Glennon and colleagues by 2004.^[1]

2C-B-morpholine

Clinical data
Other names	2C-B-Norphenmetrazine; 2-(4-Bromo-2,5-dimethoxyphenyl)morpholine
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor ligand
ATC code	None
Identifiers
IUPAC name 2-(4-bromo-2,5-dimethoxyphenyl)morpholine
CAS Number	807631-07-8
PubChem CID	11429275
ChemSpider	9604151
ChEMBL	ChEMBL191154
Chemical and physical data
Formula	C12H16BrNO3
Molar mass	302.168 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C=C1C2CNCCO2)OC)Br
InChI InChI=1S/C12H16BrNO3/c1-15-10-6-9(13)11(16-2)5-8(10)12-7-14-3-4-17-12/h5-6,12,14H,3-4,7H2,1-2H3 Key:OUTZYBJUJMETRJ-UHFFFAOYSA-N

See also

• Substituted phenethylamine § Cyclized phenethylamines
• Substituted phenylmorpholine
• 2C-B-aminorex
• 2C-B-BZP
• 2C-B-PP