TFMBOX is a putative

serotonergic psychedelic 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 halluci ...

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 benzoxepin ("BOX") families. It is the

cyclized phenethylamine Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by ...

analogue of DOTFM and

2C-TFM 2C-TFM, also known as 4-trifluoromethyl-2,5-dimethoxyphenethylamine, is a serotonin 5-HT2 receptor agonist and psychedelic drug of the phenethylamine and 2C families. It has also been called 2C-CF3, a name derived from the '' para''-trifluorom ...

in which the α carbon has been connected to the 2-

methoxy group 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 ...

via an ethyl

chain A chain is a serial assembly of connected pieces, called links, typically made of metal, with an overall character similar to that of a rope in that it is flexible and curved in compression but linear, rigid, and load-bearing in tension. A ...

to form a benzoxepin

ring system A ring system is a disc or torus orbiting an astronomical object that is composed of solid material such as dust, meteoroids, planetoids, moonlets, or stellar objects. Ring systems are best known as planetary rings, common components of sate ...

. The drug was assessed at and showed

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 and 5-HT_1A receptors, with K_i values of 340nM and 1,300nM, respectively. Its affinity for the serotonin 5-HT_2A receptor was about 15-fold lower than that of

DOB DOB or Dob often refers to date of birth. DOB or Dob may also refer to: Biochemistry * 2,5-dimethoxy-4-bromoamphetamine, Bromo-DMA, a psychedelic drug ** Meta-DOB, related substance ** Methyl-DOB, related substance * HLA-DOB, human gene Organiz ...

and DOI, whereas its affinity for the serotonin 5-HT_1A receptor was the same as that of DOI and was about half that of DOB. TFMBOX also very weakly inhibited the reuptake of serotonin ( = 9,900nM), but did not affect

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic compound, organic chemical in the catecholamine family that functions in the brain and human body, body as a hormone, neurotransmitter and neuromodulator. The ...

reuptake Reuptake is the reabsorption of a neurotransmitter by a neurotransmitter transporter located along the plasma membrane of an axon terminal (i.e., the pre-synaptic neuron at a synapse) or glial cell after it has performed its function of transmi ...

( = >50,000–100,000nM). The drug fully substituted for

LSD Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a semisynthetic, hallucinogenic compound derived from ergot, known for its powerful psychological effects and serotonergic activity. I ...

in rodent

drug discrimination Drug discrimination (DD) is a technique in behavioral neuroscience used to evaluate the discriminative stimulus properties or interoceptive cues of psychoactive drugs. In drug discrimination, a subject is trained on a training drug, and then i ...

tests, albeit with about one-third of the

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 ...

of DOB and

2C-B 2C-B, also known as 4-bromo-2,5-dimethoxyphenethylamine or by the slang name Nexus, is a synthetic psychedelic drug of the 2C family, mainly used as a recreational drug. It was first synthesized by Alexander Shulgin in 1974 for use in psychoth ...

. TFMBOX was first described in the

scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...

by Nick Cozzi, a student of David E. Nichols, by 1994. Other "BOX" drugs that were assessed by the group include BOX (the cyclized analogue of

2C-H 2C-H, also known as 2,5-dimethoxyphenethylamine (2,5-DMPEA), is a lesser-known drug of the phenethylamine and 2C (4-substituted 2,5-dimethoxyphenethylamine) families. It is the parent compound of the 2C drugs. Use and effects There is no re ...

and DOH), BBOX (the cyclized analogue of 2C-B and DOB), and IBOX (the cyclized analogue of

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 ...

and DOI). However, BBOX and IBOX only partially substituted for LSD in drug discrimination tests.

References

External links

TFMBOX - Isomer Design

POD 81: Dr. Carl Hart and Dr. Nicholas Cozzi at the MAPS conference - Hamilton Morris - The Hamilton Morris Podcast

POD 69: The Alchemist with Dr. Tarik Peterson - Hamilton Morris - The Hamilton Morris Podcast

POD 99: February Q&A (finally) - Hamilton Morris - The Hamilton Morris Podcast
{{Phenethylamines Benzoxepines Methoxy compounds Psychedelic phenethylamines Serotonin receptor modulators Trifluoromethyl compounds Secondary amines

See also

References

External links