2C-T-33, also known as 4-(3-methoxybenzylthio)-2,5-dimethoxyphenethylamine, is a

serotonin receptor agonist A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin (5-hydroxytryptamine; 5-HT), a neurotransmitter and hormone and the endogenous ligand of t ...

of the

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 ...

and 2C families. It was first synthesized and described 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 ...

in 2003. The drug is not known to have ever been tested in humans and its active human doses have not been reported.

Pharmacology

2C-T-33 shows high

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

for the

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT_2A receptor (K_i = 1.7nM) and to a much lesser extent for the serotonin 5-HT_2C receptor (K_i = 75nM; 44-fold lower than for 5-HT_2A). In terms of serotonin 5-HT_2A receptor activation, its is 26nM and its is 40%. Hence, 2C-T-33 acts as a low-efficacy

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 ...

of the serotonin 5-HT_2A receptor. The drug shows higher affinity for the serotonin 5-HT_2A receptor but much lower

potency Potency may refer to: * Potency (pharmacology), a measure of the activity of a drug in a biological system * Virility * Cell potency, a measure of the differentiation potential of stem cells * In homeopathic dilutions, potency is a measure of ho ...

and efficacy in activating the receptor compared to 2C-T or 2C-B (which had values of K_i = 6.9–49nM, = 2.0–2.1nM, and = 75–92%). In contrast to most other 2C drugs and serotonergic psychedelics, 2C-T-33 appears to be completely inactive as an agonist of the serotonin 5-HT_2B receptor ( > 10,000nM). The drug has also been assessed at a number of other

target Target may refer to: Warfare and shooting * Shooting target, used in marksmanship training and various shooting sports ** Bullseye (target), the goal one for which one aims in many of these sports ** Aiming point, in field artille ...

s. The drug did not significantly produce the

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 ...

(HTR), a behavioral proxy of psychedelic effects, in rodents, and hence may not have

hallucinogen 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 ...

ic effects in humans. Its analogue 2C-T-27 (which lacks the

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

group on the added benzyl ring) significantly and potently induces the HTR in rodents. However, the HTR induced by 2C-T-27 is far weaker in magnitude than that induced by other 2C-T-X drugs and other serotonergic psychedelics. For example, 2C-T (or 2C-T-1) induced about 7-fold more HTR events than 2C-T-33. In contrast to the lack of assessment of 2C-T-33 in humans, 2C-T-27 has been evaluated and found to be active as a psychedelic in humans with a dose range of 80 to 130mg. The lack of HTR with 2C-T-33 may be due to its low-efficacy partial agonism of the serotonin 5-HT_2A receptor and the receptor not being activated strongly enoughly. The potencies of psychedelics in inducing the HTR are positively correlated with their efficacies in activating the serotonin 5-HT_2A receptor. The bulky 4 substitution of 2C-T-33 may be too large to accommodate the binding pocket of the serotonin 5-HT_2A receptor in terms of maintaining robust receptor activation. Similar findings have been observed for other phenethylamines with bulky 4-position substitutions, such as DOHx, DOBz, and 4-PhPr-3,5-DMA. In addition to its potential psychoactive effects, 2C-T-33 has shown

anti-inflammatory Anti-inflammatory is the property of a substance or treatment that reduces inflammation, fever or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs reduce pain by inhibiting mechan ...

effects in animal studies similarly to other serotonin 5-HT_2A receptor agonists and serotonergic psychedelics. However, 2C-T-33 was the least effective assessed phenethylamine and was far less effective than other phenethylamines such as

2C-I 2C-I, also known as 2,5-dimethoxy-4-iodophenethylamine, is a phenethylamine of the 2C family with psychedelic effects. It was first synthesized by Alexander Shulgin, and is described in Shulgin's book ''PiHKAL'' (1991). The substance is con ...

, DOIB, 2C-B, (''R'')-DOI, and

2,5-DMA 2,5-Dimethoxyamphetamine (2,5-DMA), also known as DMA-4 or as DOH, is a drug of the substituted phenethylamine, phenethylamine and substituted amphetamine, amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional iso ...

, among others.

References

External links

2C-T-33 - isomer design
{{Phenethylamines 2C (psychedelics) Anti-inflammatory agents Non-hallucinogenic 5-HT2A receptor agonists Serotonin receptor agonists TAAR1 modulators Thioethers 3-Methoxyphenyl compounds

Pharmacology

See also

References

External links