Thiobuscaline

Thiobuscaline
Clinical data
Other names	TB; 4-Thiobuscaline; 4-TB; 4-Butylthio-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-butylthiophenethylamine
Routes of; administration	Oral
Drug class	Psychoactive drug; Antidepressant
ATC code	None;
Pharmacokinetic data
Duration of action	~8 hours
Identifiers
	IUPAC name 2-[4-(butylsulfanyl)-3,5-dimethoxyphenyl]ethan-1-amine;
CAS Number	90109-57-2 ;
PubChem CID	44349865;
ChemSpider	21106390 ;
UNII	45ZTS7GX2F;
ChEMBL	ChEMBL123840 ;
CompTox Dashboard (EPA)	DTXSID80658366 ;
Chemical and physical data
Formula	C14H23NO2S
Molar mass	269.40 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cc(cc(OC)c1SCCCC)CCN;
	InChI InChI=1S/C14H23NO2S/c1-4-5-8-18-14-12(16-2)9-11(6-7-15)10-13(14)17-3/h9-10H,4-8,15H2,1-3H3 ; Key:CPNWMHCBHUXITO-UHFFFAOYSA-N ;
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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]

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] 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]

The chemical synthesis of thiobuscaline has been described.^[1] Analogues of thiobuscaline include 4-thiomescaline, 4-thioescaline, and thioproscaline (4-thioproscaline), among others.^[1]^[2]^[3]

Thiobuscaline was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1984.^[4] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.^[1]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://www.erowid.org/library/books_online/pihkal/pihkal149.shtml
^ ^a ^b ^c ^d ^e Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025.
^ ^a ^b ^c ^d ^e Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
^ Jacob P, Shulgin AT (July 1984). "Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothio analogues". J Med Chem. 27 (7): 881–888. doi:10.1021/jm00373a013. PMID 6737431. Archived from the original on 2025-07-12.

External links

[PiHKAL-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://www.erowid.org/library/books_online/pihkal/pihkal149.shtml

[JacobShulgin1994-2] Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025.

[Shulgin2003-3] Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.

[JacobShulgin1984-4] Jacob P, Shulgin AT (July 1984). "Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothio analogues". J Med Chem. 27 (7): 881–888. doi:10.1021/jm00373a013. PMID 6737431. Archived from the original on 2025-07-12.

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[2]

[3]

[4]

See also

References

External links