2-Thioisomescaline

2-Thioisomescaline.svg skin-invert-image 250px Oral Psychoactive drug None Unknown 75510-74-6 20337296 15283967 L9542D99QQ 281325 2-TIM; 2-Methylthio-3,4-dimethoxyphenethylamine; 3,4-Dimethoxy-2-methylthiophenethylamine 2-(3,4-dimethoxy-2-methylsulfanylphenyl)ethanamine 11 17 1 2 1 COC1=C(C(=C(C=C1)CCN)SC)OC 1S/C11H17NO2S/c1-13-9-5-4-8(6-7-12)11(15-3)10(9)14-2/h4-5H,6-7,12H2,1-3H3 NJNFCDQQEIAOIF-UHFFFAOYSA-N 2-Thioisomescaline (2-TIM), also known as 2-methylthio-3,4-dimethoxyphenethylamine, is a chemical compound of the phenethylamine and scaline families related to mescaline. https://www.erowid.org/library/books_online/pihkal/pihkal152.shtml Jacob P, Shulgin AT Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs 74–91 Lin GC, Glennon RA Hallucinogens: An Update National Institute on Drug Abuse Research Monograph Series 146 1994 National Institute on Drug Abuse 8742795 https://archives.nida.nih.gov/sites/default/files/monograph146.pdf https://bibliography.maps.org/resources/download/11534 https://web.archive.org/web/20250713011914/https://bibliography.maps.org/resources/download/11534 13 July 2025 Shulgin AT Laing RR Basic Pharmacology and Effects Hallucinogens: A Forensic Drug Handbook 67–137 2003 Elsevier Science Forensic Drug Handbook Series 978-0-12-433951-4 https://books.google.com/books?id=l1DrqgobbcwC https://bibliography.maps.org/resources/download/12634 https://web.archive.org/web/20250713013624/https://bibliography.maps.org/resources/download/12634 13 July 2025 It is the analogue of isomescaline in which the methoxy group at the 2 position has been replaced with a methylthio group. The compound is one of two possible thioisomescaline (TIM) positional isomers, the others being 3-thioisomescaline (3-TIM) and 4-thioisomescaline (4-TIM). In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2-TIM's dose as greater than 240mg orally and its duration as unknown. At a dose of 160mg orally, there was some brief possible awareness. In addition, a small amount of alcohol later that day was quite intoxicating. On the other hand, there were no effects whatsoever at a higher dose of 240mg orally. Shulgin concluded that 2-TIM is inactive. The chemical synthesis of 2-TIM has been described. 2-TIM was first described in the scientific literature by Shulgin and Peyton Jacob III in 1981. Jacob P, Shulgin AT Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline J Med Chem 24 11 1348–1353 November 1981 7310812 10.1021/jm00143a017 https://bibliography.maps.org/resources/download/8602 https://web.archive.org/web/20250712232400/https://bibliography.maps.org/resources/download/8602 2025-07-12 Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991. See also Scaline 3-Thioisomescaline 4-Thioisomescaline References External links 2-TIM (2-Thioisomescaline) - Isomer Design 2-TIM (2-Thioisomescaline) - PiHKAL - Erowid 2-TIM (2-Thioisomescaline) - PiHKAL - Isomer Design Category:Methoxyphenethylamines Category:Methylthio compounds Category:Phenol ethers Category:PiHKAL Category:Psychoactive drugs Category:Thioscalines