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2T-2CTFM-3PIP

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2T-2CTFM-3PIP
Clinical data
Other names2T-2C-TFM-3PIP; 2-Thio-LPH-5; 2-Thio-2C-TFM-3PIP; 2C-2-TOTFM-3PIP; 3-(5-Methoxy-2-methylthio-4-(trifluoromethyl)phenyl)piperidine
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 3-[5-methoxy-2-(methylsulfanyl)-4-(trifluoromethyl)phenyl]piperidine
Chemical and physical data
FormulaC14H18F3NOS
Molar mass305.36 g·mol−1
3D model (JSmol)
  • CSc1cc(c(cc1C1CCCNC1)OC)C(F)(F)F
  • InChI=1S/C14H18F3NOS/c1-19-12-6-10(9-4-3-5-18-8-9)13(20-2)7-11(12)14(15,16)17/h6-7,9,18H,3-5,8H2,1-2H3
  • Key:RMTQZJORMPTXEF-UHFFFAOYSA-N

2T-2CTFM-3PIP, also known as 3-(5-methoxy-2-methylthio-4-(trifluoromethyl)phenyl)piperidine or as 2-thio-LPH-5, is a serotonin receptor modulator of the phenethylamine, thio-2C, and 3-phenylpiperidine (3PIP) families related to 2C-TFM and LPH-5 ((S)-2C-TFM-3PIP).[1] It is a cyclized phenethylamine and is the analogue of 2C-TFM in which the methoxy group at the 2 position has been replaced with a methylthio group and in which the β position has been connected to the amine to form a piperidine ring.[1] The drug is also the analogue of LPH-5 in which the 2-methoxy group has been replaced with a 2-methylthio group.[1]

2T-2CTFM-3PIP is a racemic mixture of (R)- and (S)- enantiomers.[1] Both enantiomers are potent and high-efficacy serotonin 5-HT2A receptor agonists.[1] They also show less-potent serotonin 5-HT2B and 5-HT2C receptor agonism.[1] The (S)- enantiomer, (S)-2T-2CTFM-3PIP, was the most potent serotonin 5-HT2A receptor agonist of a large series of evaluated 3PIP derivatives.[1] It had about 1.4- to 2.3-fold higher activational potency at the serotonin 5-HT2A receptor than LPH-5.[1] Unlike LPH-5, 2T-2CTFM-3PIP was not assessed in the head-twitch response test nor in other animal studies.[1]

2T-2CTFM-3PIP was patented and first described in the literature by Emil Märcher-Rørsted and colleagues in association with Lophora in 2021.[1] It is one of only a handful of thio-2Cs (as in 2- and/or 5-thio-substituted 2Cs) to have been described, with other examples including Alexander Shulgin's 2C-2-TOM (2-thio-2C-D) and 2C-5-TOET (5-thio-2C-E), which were mentioned in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) and other publications.[1][2][3]

See also

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References

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  1. 1 2 3 4 5 6 7 8 9 10 11 US 2021/0137908, Kristensen JL, Jensen AA, Märcher-Rørsted E, "5-HT2A Agonists for Use in Treatment of Depression.", published 13 May 2021, assigned to Lophora ApS.
  2. ↑ Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  3. ↑ Jacob P, Shulgin AT (May 1983). "Sulfur analogues of psychotomimetic agents. 2. Analogues of (2,5-dimethoxy-4-methylphenyl)-and (2,5-dimethoxy-4-ethylphenyl)isopropylamine". Journal of Medicinal Chemistry. 26 (5): 746–752. doi:10.1021/jm00359a021. PMID 6842515.
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