2C-T-16

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]

2C-T-16

Clinical data
Other names	2,5-Dimethoxy-4-allylthiophenethylamine; 4-Allylthio-2,5-dimethoxyphenethylamine
Routes of administration	Oral[1]
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Duration of action	4–6 hours[1]
Identifiers
IUPAC name 2-{{#parsoidfragment:2}}{2,5-Dimethoxy-4-[(prop-2-en-1-yl)sulfanyl]phenyl}ethan-1-amine
CAS Number	748131-14-8 Y 648957-42-0 (hydrochloride)
PubChem CID	12063256
ChemSpider	58191439 Y
UNII	CNK5SS3A5Q
CompTox Dashboard (EPA)	DTXSID301032255
Chemical and physical data
Formula	C13H19NO2S
Molar mass	253.36 g·mol−1
3D model (JSmol)	Interactive image
Melting point	193 to 194 °C (379 to 381 °F)
SMILES COc1cc(SCC=C)c(OC)cc1CCN
InChI 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

Use and effects

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

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

Pharmacology

Pharmacodynamics

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.^[1]: 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.^[4]

Society and culture

Legal status

Canada

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

See also

• 2C (psychedelics)
• 2C-AL
• 2C-T-3
• 2C-T-28
• 2C-T-29
• 3C-AL