2C-TFM
Encyclopedia
2C-TFM is a psychedelic
phenethylamine
of the 2C family
. It was first synthesized in the laboratory of David E. Nichols
. It has also been called 2C-CF3, a name derived from the para-trifluoromethyl group it contains.
phenethylamine
. The full name of the chemical is 2-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]ethanamine.
because of its structural similarities to 2C-B
and 2C-T-7
. However, 2C-TFM, unlike many other phenethylamines, has not been widely sold by internet retailers. In the wake of Operation Web Tryp
in July 2004, the issue of possession and sales of 2C-TFM and other similar chemicals will probably be resolved in the courtroom as well the fate of this rare but unique psychedelic
. There have been no reported deaths or hospitalizations from 2C-TFM.
serotonin receptor
agonist
in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines. 2C-TFM displaced radiolabelled ketanserin
from 5-HT2A/C receptors with a Ki of 74.5, as compared to a Ki of 80.9 for the more well known 5-HT2A agonist DOI
, indicating similar binding affinity at the receptor.
Psychedelic
The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...
phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
of the 2C family
2C (psychedelics)
2C is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of the benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and longer acting...
. It was first synthesized in the laboratory of David E. Nichols
David E. Nichols
David E. Nichols is an American pharmacologist and medicinal chemist.Presently the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichols has worked in the field of psychoactive drugs since 1969...
. It has also been called 2C-CF3, a name derived from the para-trifluoromethyl group it contains.
Chemistry
2C-TFM is a code that represents 4-trifluoromethyl-2,5-dimethoxyMethoxy
In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...
phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
. The full name of the chemical is 2-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]ethanamine.
Effects
Very little data exists, but some reports suggest 2C-TFM produces psychedelic (hallucinogenic/entheogenic) effects that may last 8–16 hours.Legality
2C-TFM is unscheduled and uncontrolled in the United States, but possession and sales of 2C-TFM could potentially be prosecuted under the Federal Analog ActFederal Analog Act
The Federal Analog Act, , is a controversial section of the United States Controlled Substances Act which allowed any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were also listed in those schedules, but only if intended for human...
because of its structural similarities to 2C-B
2C-B
2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred...
and 2C-T-7
2C-T-7
2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book PiHKAL: A Chemical Love Story, Alexander Shulgin lists the dosage range as 10 to 30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours...
. However, 2C-TFM, unlike many other phenethylamines, has not been widely sold by internet retailers. In the wake of Operation Web Tryp
Operation Web Tryp
Operation Web Tryp was a United States Drug Enforcement Administration operation that ended on July 21, 2004 with the arrests of 10 persons. Its purpose was to investigate web sites suspected of distribution of unscheduled, unregulated tryptamines and phenethylamines of questionable legality...
in July 2004, the issue of possession and sales of 2C-TFM and other similar chemicals will probably be resolved in the courtroom as well the fate of this rare but unique psychedelic
Psychedelic
The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...
. There have been no reported deaths or hospitalizations from 2C-TFM.
Pharmacology
The mechanism that produces the hallucinogenic and entheogenic effects of 2C-TFM is most likely to result from action as a 5-HT2A5-HT2A receptor
The mammalian 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor . This is the main excitatory receptor subtype among the GPCRs for serotonin , although 5-HT2A may also have an inhibitory effect on certain areas such...
serotonin receptor
5-HT receptor
The serotonin receptors, also known as 5-hydroxytryptamine receptors or 5-HT receptors, are a group of G protein-coupled receptors and ligand-gated ion channels found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory neurotransmission...
agonist
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines. 2C-TFM displaced radiolabelled ketanserin
Ketanserin
Ketanserin is a drug with affinity for multiple G protein-coupled receptors . Initially it was believed to be a highly selective antagonist for serotonin 5-HT2A receptors, however this is not true. Ketanserin only has moderate selectivity for 5-HT2A receptors over 5-HT2C receptors...
from 5-HT2A/C receptors with a Ki of 74.5, as compared to a Ki of 80.9 for the more well known 5-HT2A agonist DOI
2,5-Dimethoxy-4-iodoamphetamine
2,5-dimethoxy-4-iodoamphetamine is a psychedelic drug and a substituted amphetamine of the phenethylamine family. It is also a powerful anti-inflammatory that is effective at doses on the order of 100 micrograms in humans, far below its effective dose as a psychedelic. Despite being a substituted...
, indicating similar binding affinity at the receptor.