2C-B-3PIP

2C-B-3PIP, also known as 3-piperidine, is a serotonin receptor modulator of the phenethylamine, 2C, and 3-phenylpiperidine families related to the psychedelic drug LPH-5. 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.

Pharmacology

Pharmacodynamics

The drug is a racemic mixture of - and - enantiomers. The eutomer or - enantiomer is a serotonin 5-HT_2A receptor partial agonist with an of 69nM and an of 37%, whereas this enantiomer was inactive as an agonist of the serotonin 5-HT_2C receptor and instead showed low-potency antagonism at this receptor with an of 640nM. The distomer or - enantiomer is a serotonin 5-HT_2A receptor partial agonist with an of 370nM and of 67% as well as a serotonin 5-HT_2C receptor partial agonist with an of 1,900nM and of 34%. The enantiomers are both dramatically less potent as serotonin 5-HT_2A and 5-HT_2C receptor agonists than 2C-B, which had an of 1.6nM at the serotonin 5-HT_2A receptor and an of 4.1nM at the serotonin 5-HT_2C receptor. 2C-B-3PIP and its enantiomers were not assessed in animal behavioral studies and it is unknown whether they produce psychedelic-type effects.

Chemistry

The chemical synthesis of 2C-B-3PIP has been described. Derivatives of 2C-B-3PIP include the NBOMe-like 2C-B-3PIP-NBOMe and 2C-B-3PIP-POMe. Some notable analogues of 2C-B-3PIP include 2C-B, LPH-5, 2C-B-PYR, ZC-B, 2C-B-morpholine, 2C-B-aminorex, 2C-B-PP, and DMBMPP, among others.

History

2C-B-3PIP was first described in the scientific literature by Martin Hansen in 2010. Its pharmacology was subsequently described by Emil Märcher-Rørsted and colleagues in association with Lophora in the 2020s. 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.