Thiobuscaline
Pharmaceutical compound
From Wikipedia, the free encyclopedia
Thiobuscaline (TB), or 4-thiobuscaline (4-TB), also known as 3,5-dimethoxy-4-butylthiophenethylamine, is a psychoactive drug of the phenethylamine and scaline families related to the psychedelic drug mescaline.[1][2][3] It is the analogue of buscaline in which the butoxy group at the 4 position has been replaced with a butylthio group.[1][2][3] The drug is a non-hallucinogenic serotonin 5-HT2A receptor agonist with similar effects and potential uses to those of Ariadne.[1][4]
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| Other names | TB; 4-Thiobuscaline; 4-TB; 4-Butylthio-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-butylthiophenethylamine |
| Routes of administration | Oral[1] |
| Drug class | Non-hallucinogenic serotonin 5-HT2A and 5-HT2C receptor agonist; Psychoactive drug; Antidepressant |
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| Onset of action | ~1 hour[1] |
| Duration of action | ~8 hours[1] |
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| Formula | C14H23NO2S |
| Molar mass | 269.40 g·mol−1 |
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Use and effects
In his book PiHKAL (Phenethylamines I Have Known And Loved) and other publications, Alexander Shulgin lists thiobuscaline's dose range as 60 to 120 mg orally and its duration as about 8 hours.[1][2][3] Its onset is about 1 hour.[1] The effects of thiobuscaline have been reported to include a "benign and beautiful experience which never quite popped into anything psychedelic", subtle threshold effects, a vague awareness of something, being in a "wonderful place spiritually" but with "some dark edges", it being "pleasant, but certainly not psychedelic", and body discomfort.[1] No clear hallucinogenic effects were described.[1] Thiobuscaline is listed as being 4 times more potent as a psychoactive drug than mescaline.[2][3]
Thiobuscaline produced perpetual threshold psychoactive effects that did not further increase across a wide dose range of 35 to 120 mg orally.[1] Shulgin described it as "always the simple and ephemeral catalyst of euphoria without substance and without body".[1] In addition, he said that it could not easily be classified, for instance as a psychedelic or stimulant.[1] Instead, Shulgin likened thiobuscaline to Ariadne (4C-D), which he noted had been called an "antidepressant".[1] He hypothesized that thiobuscaline might be beneficial for treatment of depression in certain people in the exact same way as Ariadne.[1]
Interactions
Pharmacology
Pharmacodynamics
Thiobuscaline shows affinity for the serotonin 5-HT2A receptor (Ki = 602 nM).[4] It is a potent near-full agonist of the serotonin 5-HT2A and 5-HT2C receptors and to a much lesser extent a moderate-efficacy partial agonist of the serotonin 5-HT2B receptor, with EC50 (Emax) values of 3.86 nM (114%) at the serotonin 5-HT2A receptor, 89.6 nM (55.7%) at the serotonin 5-HT2B receptor, and 8.86 nM (95.9%) at the serotonin 5-HT2C receptor.[4] Conversely, it was inactive as an agonist of the serotonin 5-HT1A receptor.[4] The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[4]
Pharmacokinetics
The in-vitro metabolism of thiobuscaline has been studied.[4]
Chemistry
Synthesis
The chemical synthesis of thiobuscaline has been described.[1][4]
Analogues
Analogues of thiobuscaline include 4-thiomescaline, 4-thioescaline, and thioproscaline (4-thioproscaline), among others.[1][2][3][4]
History
Thiobuscaline was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1984.[5] Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.[1]
Society and culture
Legal status
Canada
Thiobuscaline is not a controlled substance in Canada as of 2025.[6]
United States
Thiobuscaline is not an explicitly controlled substance in the United States.[7] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.