2C-B-3PIP

2C-B-3PIP, also known as 3-(4-bromo-2,5-dimethoxyphenyl)piperidine, is a serotonin receptor modulator of the phenethylamine, 2C, and 3-phenylpiperidine (3PIP) families related to the psychedelic drug LPH-5 ((S)-2C-TFM-3PIP).^[1][2][3][4] It is a cyclized phenethylamine and is the derivative of 2C-B in which the β position has been connected to the amine to form a piperidine ring.^[1][2][3][4]

2C-B-3PIP

Clinical data
Other names	3-(4-Bromo-2,5-dimethoxyphenyl)piperidine; β,N-Trimethylene-2C-B
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code	None
Identifiers
IUPAC name 3-(4-bromo-2,5-dimethoxyphenyl)piperidine
PubChem CID	82135182
ChemSpider	25749717
Chemical and physical data
Formula	C13H18BrNO2
Molar mass	300.196 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C=C1C2CCCNC2)OC)Br
InChI InChI=1S/C13H18BrNO2/c1-16-12-7-11(14)13(17-2)6-10(12)9-4-3-5-15-8-9/h6-7,9,15H,3-5,8H2,1-2H3 Key:ULJHXMHMDJQESG-UHFFFAOYSA-N

Pharmacology

Pharmacodynamics

The drug is a racemic mixture of (R)- and (S)- enantiomers.^[4] The eutomer or (S)- enantiomer is a serotonin 5-HT_2A receptor partial agonist with an EC₅₀Tooltip half-maximal effective concentration of 69 nM and an E_maxTooltip maximal efficacy of 37%, whereas this enantiomer was inactive as an agonist of the serotonin 5-HT_2C receptor (EC₅₀ = >50,000 nM) and instead showed low-potency antagonism at this receptor with an IC₅₀Tooltip half-maximal inhibitory concentration of 640 nM.^[4] The distomer or (R)- enantiomer is a serotonin 5-HT_2A receptor partial agonist with an EC₅₀ of 370 nM and E_max of 67% as well as a serotonin 5-HT_2C receptor partial agonist with an EC₅₀ of 1,900 nM and E_max of 34%.^[4] The enantiomers are both dramatically less potent as serotonin 5-HT_2A and 5-HT_2C receptor agonists than 2C-B, which had an EC₅₀ (E_max) of 1.6 nM (68%) at the serotonin 5-HT_2A receptor and an EC₅₀ (E_max) of 4.1 nM (74%) at the serotonin 5-HT_2C receptor.^[4] 2C-B-3PIP and its enantiomers were not assessed in animal behavioral studies and it is unknown whether they produce psychedelic-type effects.^[3][4]

Chemistry

The chemical synthesis of 2C-B-3PIP has been described.^[1][2][4] Derivatives of 2C-B-3PIP include the NBOMe-like 2C-B-3PIP-NBOMe and 2C-B-3PIP-POMe.^[1][2][5] Some notable analogues of 2C-B-3PIP include 2C-B, LPH-5 ((S)-2C-TFM-3PIP), 2C-B-PYR, ZC-B (2C-B-AZET), 2C-B-morpholine (2C-B-MOR), 2C-B-aminorex (2C-B-AR), 2C-B-PP, and DMBMPP, among others.^[4][5][1]

History

2C-B-3PIP was first described in the scientific literature by Martin Hansen in 2010.^[1] Its pharmacology was subsequently described by Emil Märcher-Rørsted and colleagues in association with Lophora in the 2020s.^[3][4] The closely related drug LPH-5, which is a selective serotonin 5-HT_2A receptor agonist and psychedelic drug, is under development by Lophora for the treatment of major depressive disorder.^{[6][4][7][8][9]}

See also

• Cyclized phenethylamine
• Substituted 3-phenylpiperidine
• Partial ergoline