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2C-T-16

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2C-T-16
Names
IUPAC name
2-[2,5-Dimethoxy-4-(prop-2-en-1-ylsulfanyl)phenyl]ethan-1-amine
Identifiers
3D model (JSmol)
  • 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 253.360 g/mol
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 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 44nM at 5-HT2A and 15nM at 5-HT2C.[3]: 791 

Legality

Canada

As of October 31, 2016, 2C-T-16 is a controlled substance (Schedule III) in Canada.[4]

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. ^ a b Daniel Trachsel; David Lehmann; Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4. {{cite book}}: Unknown parameter |last-author-amp= ignored (|name-list-style= suggested) (help)
  4. ^ http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php

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