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2C-T-33
Pharmaceutical compound From Wikipedia, the free encyclopedia
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2C-T-33, also known as 4-(3-methoxybenzylthio)-2,5-dimethoxyphenethylamine, is a serotonin receptor agonist of the phenethylamine and 2C families.[1][2][3] It was first synthesized and described by Daniel Trachsel in 2003.[2][3] The drug is not known to have ever been tested in humans and its active human doses have not been reported.[3][4]
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2C-T-33 shows high affinity for the serotonin 5-HT2A receptor (Ki = 1.7 nM) and to a much lesser extent for the serotonin 5-HT2C receptor (Ki = 75 nM; 44-fold lower than for 5-HT2A).[5] In terms of serotonin 5-HT2A receptor activation, its EC50 is 26 nM and its Emax is 40%.[5] Hence, 2C-T-33 acts as a low-efficacy partial agonist of the serotonin 5-HT2A receptor.[6][5][7] The drug shows higher affinity for the serotonin 5-HT2A receptor but much lower potency and efficacy in activating the receptor compared to 2C-T or 2C-B (which had values of Ki = 6.9–49 nM, EC50 = 2.0–2.1 nM, and Emax = 75–92%).[5] In contrast to most other 2C drugs and serotonergic psychedelics, 2C-T-33 appears to be completely inactive as an agonist of the serotonin 5-HT2B receptor (EC50 > 10,000 nM).[5] The drug has also been assessed at a number of other targets.[5]
The drug did not significantly produce the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents, and hence may not have hallucinogenic effects in humans.[6] Its analogue 2C-T-27 (which lacks the methoxy group on the added benzyl ring) significantly and potently induces the HTR in rodents.[6] However, the HTR induced by 2C-T-27 is far weaker in magnitude than that induced by other 2C-T-X drugs and other serotonergic psychedelics.[6] For example, 2C-T (or 2C-T-1) induced about 7-fold more HTR events than 2C-T-33.[6] In contrast to the lack of assessment of 2C-T-33 in humans, 2C-T-27 has been evaluated and found to be active as a psychedelic in humans with a dose range of 80 to 130 mg.[6][1]
The lack of HTR with 2C-T-33 may be due to its low-efficacy partial agonism of the serotonin 5-HT2A receptor and the receptor not being activated strongly enoughly.[6] The potencies of psychedelics in inducing the HTR are positively correlated with their efficacies in activating the serotonin 5-HT2A receptor.[6] The bulky 4 substitution of 2C-T-33 may be too large to accommodate the binding pocket of the serotonin 5-HT2A receptor in terms of maintaining robust receptor activation.[6] Similar findings have been observed for other phenethylamines with bulky 4-position substitutions, such as DOHx, DOBz, and 4-PhPr-3,5-DMA.[6]
In addition to its potential psychoactive effects, 2C-T-33 has shown anti-inflammatory effects in animal studies similarly to other serotonin 5-HT2A receptor agonists and serotonergic psychedelics.[7] However, 2C-T-33 was the least effective assessed phenethylamine and was far less effective than other phenethylamines such as 2C-I, DOIB, 2C-B, (R)-DOI, and 2,5-DMA, among others.[7]
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