2C-B-3PIP-POMe

2C-B-3PIP-POMe
Clinical data
Drug class	Serotonin receptor modulator; Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist
ATC code	None;
Identifiers
	IUPAC name 5-(4-bromo-2,5-dimethoxyphenyl)-2-(2-methoxyphenyl)piperidine;
PubChem CID	156735247;
Chemical and physical data
Formula	C20H24BrNO3
Molar mass	406.320 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC=CC=C1C2CCC(CN2)C3=CC(=C(C=C3OC)Br)OC;
	InChI InChI=1S/C20H24BrNO3/c1-23-18-7-5-4-6-14(18)17-9-8-13(12-22-17)15-10-20(25-3)16(21)11-19(15)24-2/h4-7,10-11,13,17,22H,8-9,12H2,1-3H3; Key:BDZXVOHNVCEDNQ-UHFFFAOYSA-N;

2C-B-3PIP-POMe is a serotonin receptor modulator of the phenethylamine, 2C, 3-phenylpiperidine (3PIP), and NBOMe families.^[1]^[2]^[3]^[4] It is a cyclized phenethylamine and along with 2C-B-3PIP-NBOMe is an NBOMe derivative of 2C-B-3PIP.^[1]^[2]^[3]^[4] The drug is a mixture of cis- and trans- isomers.^[1]^[2]^[4] Its isomers show weak affinity for the serotonin 5-HT_2A and 5-HT_2C receptors (K_i = 290–856 nM and 3,850–23,200 nM, respectively), with these affinities being profoundly reduced relative to those of 2C-B.^[1]^[2]^[4]^[5] The cis isomer is a low-potency agonist of the serotonin 5-HT_2A receptor (EC₅₀Tooltip half-maximal effective concentration = 480–2,300 nM; E_maxTooltip maximal efficacy = 87–94%), the serotonin 5-HT_2B receptor (EC₅₀ = 770 nM; E_max = 20%), and the serotonin 5-HT_2C receptor (EC₅₀ = 170–2,000 nM; E_max = 80–82%), whereas the trans isomer is inactive as an agonist of these receptors even at very high concentrations.^[3] The chemical synthesis of 2C-B-3PIP-POMe has been described.^[1]^[2]^[3] 2C-B-3PIP-POMe was first described in the scientific literature by Martin Hansen in 2010.^[1]^[2]^[3]^[4]