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2c-t-16

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Title: 2c-t-16  
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Subject: 2C (psychedelics), 2,4,5-Trimethoxyphenethylamine, 2C-G, 2C-E, 2C-D
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2c-t-16

2C-T-16
Names
IUPAC name
2-[2,5-Dimethoxy-4-(prop-2-en-1-ylsulfanyl)phenyl]ethan-1-amine
Identifiers
 Y
(HCl)
Jmol-3D images Image
PubChem
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 10-25mg and a duration of 4-6 hours,[3] 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.[4] Some related compounds have been shown to be MAOIs,[5] and this may also be the case for 2C-T-16 in addition to its 5-HT2 agonist effects.


See also

References

  1. ^  
  2. ^ Trachsel D. 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. 2003; 86(7):2610–2619. doi:10.1002/hlca.200390210
  3. ^ Daniel Trachsel, David Lehmann and Christoph Enzensperger. Phenethylamine Von der Struktur zur Funktion, pp 788-789. Nachtschatten Verlag AG, 2013. ISBN 978-3-03788-700-4
  4. ^ Ibid., p 791.
  5. ^ Gallardo-Godoy, A; Fierro A; McLean TH; Castillo M; Cassels BK; Reyes-Parada M; Nichols DE. (April 7, 2005). "Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling". Journal of Medicinal Chemistry 48 (7): 2407–19.  

External links

  • , which mentions 2C-T-16PiHKALAleph-2 Entry in


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