2C-B-3PIP
Pharmaceutical compound
From Wikipedia, the free encyclopedia
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]
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| Other names | 3-(4-Bromo-2,5-dimethoxyphenyl)piperidine; β,N-Trimethylene-2C-B |
| Drug class | Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist |
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| Formula | C13H18BrNO2 |
| Molar mass | 300.196 g·mol−1 |
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Pharmacology
Pharmacodynamics
The drug is a racemic mixture of (R)- and (S)- enantiomers.[4] The eutomer or (S)- enantiomer is a serotonin 5-HT2A receptor partial agonist with an EC50 of 69 nM and an Emax of 37%, whereas this enantiomer was inactive as an agonist of the serotonin 5-HT2C receptor (EC50 = >50,000 nM) and instead showed low-potency antagonism at this receptor with an IC50 of 640 nM.[4] The distomer or (R)- enantiomer is a serotonin 5-HT2A receptor partial agonist with an EC50 of 370 nM and Emax of 67% as well as a serotonin 5-HT2C receptor partial agonist with an EC50 of 1,900 nM and Emax of 34%.[4] The enantiomers are both dramatically less potent as serotonin 5-HT2A and 5-HT2C receptor agonists than 2C-B, which had an EC50 (Emax) of 1.6 nM (68%) at the serotonin 5-HT2A receptor and an EC50 (Emax) of 4.1 nM (74%) at the serotonin 5-HT2C 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-HT2A receptor agonist and psychedelic drug, is under development by Lophora for the treatment of major depressive disorder.[6][4][7][8][9]