:2C-T-16

{{Short description|Psychedelic drug}}

{{chembox

| ImageFile = 2CT16.svg

| PIN = 2-{2,5-Dimethoxy-4-[(prop-2-en-1-yl)sulfanyl]phenyl}ethan-1-amine

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| 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

| InChIKey = BXCMEIZBXNLJKM-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = CNK5SS3A5Q

| CASNo = 748131-14-8

| CASNo2 = 648957-42-0

| CASNo2_Comment = (HCl)

| PubChem = 12063256

| ChemSpiderID = 58191439

| SMILES = COc1cc(SCC=C)c(OC)cc1CCN

| StdInChI = 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

| StdInChIKey = BXCMEIZBXNLJKM-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=13 | H=19 | N=1 | O=2 | S=1

| Appearance =

| Density =

| MeltingPtC = 193-194

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

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.{{CitePiHKAL}} Synthesis of 2C-T-16 was finally achieved by Daniel Trachsel some years later,{{cite journal |author=Daniel Trachsel |year=2003 |title=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) |journal=Helvetica Chimica Acta |volume=86 |issue=7 |pages=2610–2619 |doi=10.1002/hlca.200390210}} 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,{{cite book |author=Daniel Trachsel |author2=David Lehmann |author3=Christoph Enzensperger |name-list-style=amp |year=2013 |title=Phenethylamine: Von der Struktur zur Funktion |publisher=Nachtschatten Verlag AG |isbn=978-3-03788-700-4}}{{rp|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-HT_2A and 15 nM at 5-HT_2C.{{rp|791}} 2C-T-16 and related derivatives are potent partial agonists of the 5-HT_1A, 5-HT_2A, 5-HT_2B and 5-HT_2C receptors and induce a head-twitch response in mice.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.{{Cite journal|doi=10.1016/j.neuropharm.2017.07.012|pmid=28720478|title=Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)|journal=Neuropharmacology|volume=134|issue=Pt A|pages=141–148|year=2018|last1=Luethi|first1=Dino|last2=Trachsel|first2=Daniel|last3=Hoener|first3=Marius C|last4=Liechti|first4=Matthias E|s2cid=7135811|url=https://edoc.unibas.ch/57358/1/20170920150712_59c2680084ec5.pdf}}