2C-T-16, also known as 4-allylthio-2,5-dimethoxyphenethylamine, is a lesser-known
psychedelic drug
Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluc ...
. It was originally named by
Alexander Shulgin
Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...
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. Synthesis of 2C-T-16 was finally achieved by
Daniel Trachsel
Daniel Trachsel is a Swiss people, Swiss chemist who studies psychedelic drug, psychedelics and entactogens. He has developed and published on a large number of novel psychedelic and entactogen chemical compound, compounds, including their psycho ...
some years later, 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,
making it around the same potency as the better-known saturated analogue
2C-T-7
2C-T-7, also known as 4-propylthio-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family. In his book '' PiHKAL: A Chemical Love Story'', Alexander Shulgin lists the dosage range as 10–30 mg. 2C-T-7 is generall ...
, but with a significantly shorter duration of action. Binding studies ''in vitro'' showed 2C-T-16 to have a
binding affinity
In biochemistry and pharmacology, a ligand is a substance that forms a complex with a biomolecule to serve a biological purpose. The etymology stems from Latin ''ligare'', which means 'to bind'. In protein-ligand binding, the ligand is usuall ...
of 44 nM at
5-HT2A and 15 nM at
5-HT2C.
2C-T-16 and related derivatives are potent
partial agonist
In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...
s of the 5-HT
1A, 5-HT
2A, 5-HT
2B and 5-HT
2C receptors and induce a
head-twitch response
The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lys ...
in mice.
Legality
Canada
As of October 31, 2016, 2C-T-16 is a controlled substance (Schedule III) in Canada.
See also
*
2C-AL
*
2C-T-3
*
2C-T-28
*
3C-AL
*
Phenethylamine
Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...
*
Psychedelics, dissociatives and deliriants
Hallucinogens, also known as psychedelics, entheogens, or historically as psychotomimetics, are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mo ...
References
External links
Aleph-2 Entry in ''PiHKAL'', which mentions 2C-T-16
{{Phenethylamines
2C (psychedelics)
Entheogens
Thioethers
Allyl compounds
Psychedelic phenethylamines