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TCB-2
Psychedelic drug From Wikipedia, the free encyclopedia
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TCB-2, also known as 2CBCB or 2C-BCB, is a putative psychedelic drug of the phenethylamine, 2C, and benzocyclobutene families related to 2C-B.[1][3][2][5] It is a cyclized phenethylamine and is the derivative of 2C-B in which the β position has been connected to the 6 position by a methylene bridge to form a benzocyclobutene ring system.[3][1][5] It is unclear whether TCB-2 produces hallucinogenic effects in humans and its route of administration and properties such as dose and duration are unknown.[1][2][3]
The drug is a highly potent serotonin receptor agonist, including of the serotonin 5-HT2A receptor among others.[3][6][1][5] TCB-2 produces psychedelic-like effects in animals.[3][1][7][8][5] It may be among the most potent known serotonin 5-HT2A receptor agonists and psychedelic phenethylamines.[3][5] TCB-2 is often employed as its more potent and selective enantiomer (R)-TCB-2 in scientific research.[3][1][5]
TCB-2 was first described in the scientific literature by Thomas McLean and colleagues of the lab of David E. Nichols at Purdue University in 2006.[1][5] It is not an explicitly controlled substance in the United States and is fully legal for use in scientific research in this country.[2][1] In 2025, TCB-2 was suggested as an alternative and replacement of the widely employed DOI for use in research.[2]
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Use and effects
TCB-2 does not appear to have been formally tested in humans and its properties and effects are unknown.[1][2][3][4] However, Daniel Trachsel has reported based on anonymous personal communication in 2009 that TCB-2 is psychoactive in the low-milligram range (route unspecified but presmably oral).[3] No additional details were provided, including notably with regard to the nature of the effects.[3] There are also a number of trip reports of TCB-2 on online forums, but such reports are unconfirmed and may not be reliable.[1] In relation to the preceding, it has been said that there are no valid data on TCB-2 in humans.[1]
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Interactions
Pharmacology
Summarize
Perspective
Pharmacodynamics
TCB-2 acts as a potent agonist of the serotonin 5-HT2A and 5-HT2C receptors.[1][3][5] Its affinity (Ki) for the serotonin 5-HT2A receptor has been reported to be 0.75 nM and to be similar to that of 2C-B (Ki = 0.88 nM).[1][3][5] The (R)-enantiomer shows 3-fold higher affinity for the serotonin 5-HT2A receptor as well as 2-fold higher activational potency at this receptor.[1][3][5] TCB-2 is a biased agonist of the serotonin 5-HT2A receptor, showing 65-fold higher potency in stimulating phosphoinositide turnover than in activating arachidonic acid release.[1][3][5] Besides the serotonin 5-HT2 receptors, TCB-2 might importantly stimulate the serotonin 5-HT1A receptor.[1][9] The comprehensive receptor interactions of TCB-2 have been studied.[6] It is a potent agonist of the serotonin 5-HT1A, 5-HT1B, 5-HT1D, 5-HT1E, 5-HT1F, 5-HT2A, 5-HT2B, and 5-HT2C receptors, with the highest activity at the serotonin 5-HT2A receptor.[6]
(R)-TCB-2 has been found to substitute for LSD and DOI in rodent drug discrimination tests.[1][3][5] It showed similar potency in this regard as LSD and 11- to 13-fold greater potency than DOI, making it one of the most potent known psychedelic drugs in this assay.[1][3][5] In contrast to (R)-TCB-2, (S)-TCB-2 was inactive in the test even at a more than 10-fold higher dose.[3][5] TCB-2 also produces the head-twitch response, another behavioral proxy of psychedelic effects, in rodents.[1][7][8][9] However, in contrast to drug discrimination, the drug required surprisingly high doses to produce the head-twitch response, showing similar potency to that of DOI in this assay.[1][8][10] This might be related to TCB-2's biased serotonin 5-HT2A receptor agonism.[1][8] In addition to its psychedelic-like effects, TCB-2 has been found to produce hyperlocomotion at lower doses and hypolocomotion at higher doses in rodents.[1][7][8][11] The drug produces rapid antidepressant-, anti-anhedonic-, and anxiolytic-like effects in animals.[12] TCB-2 shows anti-inflammatory effects in preclinical research, albeit with lower potency and efficacy than non-cyclized analogues.[13][14] Unlike other psychedelic phenethylamines, TCB-2 produces some behavioral serotonin syndrome-like effects in rodents.[1][9] Other animal studies have also been done.[8][15][16][17]
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Chemistry
Synthesis
The chemical synthesis of TCB-2 has been described.[5] The synthesis of TCB-2 has been described as tedious, such that its manufacture has been prevented from being economical, although it is still available commercially for use in scientific research.[18]
Analogues
Analogues of TCB-2 include 2C-B, DOB, β-methyl-2C-B (BMB), tomscaline, 2CB-Ind, jimscaline, LPH-5, 2CBCB-NBOMe (NBOMe-TCB-2), and ZC-B, among others.[3] 2CBCB-NBOMe, the NBOMe derivative of TCB-2, shows 2.7-fold higher affinity for the serotonin 5-HT2A receptor than TCB-2 itself.[19]
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History
TCB-2 was first described in the scientific literature by Thomas McLean and colleagues of the lab of David E. Nichols at Purdue University in 2006.[1][5] At the time of its discovery, it was the most potent known phenethylamine psychedelic, with (R)-TCB-2 having similar potency as the better-known LSD, at least on the basis of rodent drug discrimination assays.[5] However, subsequent studies using the head-twitch response found it to be much less potent.[1][7][8][9] In late 2025, TCB-2 was suggested as an alternative and replacement of the widely employed DOI for use in research.[2] This was due to DOI being poised to become a restricted Schedule I controlled substance in the United States.[2][20][21]
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Society and culture
Availability
TCB-2 is commercially available for use in scientific research.[18]
Legal status
United States
TCB-2 is not a controlled substance in the United States.[2][1] However, it could be considered an analogue of 2C-B under the Federal Analogue Act.[2] In any case, as it is not an explicitly controlled substance, there are no restrictions on use of TCB-2 for scientific research purposes.[2][1]
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See also
References
External links
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