2C-T-16

Last updated
2C-T-16
2CT16.svg
Names
Preferred IUPAC name
2-{2,5-Dimethoxy-4-[(prop-2-en-1-yl)sulfanyl]phenyl}ethan-1-amine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C13H19NO2S/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3
    Key: BXCMEIZBXNLJKM-UHFFFAOYSA-N
  • InChI=1S/C13H19NO2S/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3
    Key: BXCMEIZBXNLJKM-UHFFFAOYSA-N
  • COc1cc(SCC=C)c(OC)cc1CCN
Properties
C13H19NO2S
Molar mass 253.36 g·mol−1
Melting point 193–194 °C (379–381 °F; 466–467 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2C-T-16, also known as 4-allylthio-2,5-dimethoxyphenethylamine, is a lesser-known psychedelic drug. It was originally named by Alexander Shulgin as described in his book PiHKAL (Phenethylamines i Have Known And Loved), however while Shulgin began synthesis of this compound he only got as far as the nitrostyrene intermediate, and did not complete the final synthetic step. [1] Synthesis of 2C-T-16 was finally achieved by Daniel Trachsel some years later, [2] and it was subsequently reported as showing similar psychedelic activity to related compounds, with a dose range of 10–25 mg and a duration of 4–6 hours, [3] : 788–789  making it around the same potency as the better-known saturated analogue 2C-T-7, but with a significantly shorter duration of action. Binding studies in vitro showed 2C-T-16 to have a binding affinity of 44 nM at 5-HT2A and 15 nM at 5-HT2C. [3] : 791  2C-T-16 and related derivatives are potent partial agonists of the 5-HT1A, 5-HT2A, 5-HT2B and 5-HT2C receptors and induce a head-twitch response in mice. [4]

Contents

Legality

Canada

As of October 31, 2016, 2C-T-16 is a controlled substance (Schedule III) in Canada. [5]

See also

References

  1. ↑ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628.
  2. ↑ Daniel Trachsel (2003). "Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines)". Helvetica Chimica Acta . 86 (7): 2610–2619. doi:10.1002/hlca.200390210.
  3. 1 2 Daniel Trachsel; David Lehmann & Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN   978-3-03788-700-4.
  4. ↑ Luethi D, Trachsel D, Hoener MC, Liechti ME. Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs). Neuropharmacology. 2018 May; Volume 134, Part A: 141-148.Luethi, Dino; Trachsel, Daniel; Hoener, Marius C; Liechti, Matthias E (2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)" (PDF). Neuropharmacology. 134 (Pt A): 141–148. doi:10.1016/j.neuropharm.2017.07.012. PMID   28720478. S2CID   7135811.
  5. ↑ "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
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