2C-T-16

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2C-T-16
Clinical data
Other names2,5-Dimethoxy-4-allylthiophenethylamine; 4-Allylthio-2,5-dimethoxyphenethylamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action4–6 hours[1]
Identifiers
  • 2-{2,5-Dimethoxy-4-[(prop-2-en-1-yl)sulfanyl]phenyl}ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H19NO2S
Molar mass253.36 g·mol−1
3D model (JSmol)
Melting point193 to 194 °C (379 to 381 °F)
  • COc1cc(SCC=C)c(OC)cc1CCN
  • 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

2C-T-16, also known as 4-allylthio-2,5-dimethoxyphenethylamine, is a 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.[2] Synthesis of 2C-T-16 was finally achieved by Daniel Trachsel some years later.[3]

Use and effects

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Daniel Trachsel reported 2C-T-16 as showing similar psychedelic activity to related compounds, with a dose range of 10–25 mg and a duration of 4–6 hours,[1]: 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.

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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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.[1]: 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]

Society and culture

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Canada

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

See also

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References

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  1. ^ a b c d Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
  2. ^ Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  3. ^ Trachsel D (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.
  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 D, Trachsel D, Hoener MC, Liechti ME (May 2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)". Neuropharmacology. 134 (Pt A): 141–148. doi:10.1016/j.neuropharm.2017.07.012. PMID 28720478. S2CID 7135811.
  5. ^ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette. 4 May 2016.
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