2C-T-27
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2C-T-27
2C-T-27, also known as 4-benzylthio-2,5-dimethoxyphenethylamine, is a serotonin 5-HT2A receptor agonist and serotonergic psychedelic of the phenethylamine and 2C families. It was first synthesized and described by Daniel Trachsel in 2003. In addition to the serotonin 5-HT2A receptor, 2C-T-27 interacts with the serotonin 5-HT2C receptor. It showed higher affinity for the serotonin 5-HT2A receptor than any other 2C drug (Ki = 1.6nM), but its activational potency and efficacy were among the lowest ( = 26nM; = 27%). The drug produces the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents. However, the HTR induced by 2C-T-27 is relatively weak. 2C-T-27 has been reported to produce hallucinogenic effects in humans. Its dosage was reported by Trachsel to be 80mg or more orally and no duration was listed. See also * 2C-T-33 * 2C-T-8 * Aleph-6 * 3C-BZ * Benzscaline Benzscaline (BZ), also known as 4-benzyloxy-3,5-dimethoxyphenethylamine (4-Bzl ...
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2C-T-33
2C-T-33, also known as 4-(3-methoxybenzylthio)-2,5-dimethoxyphenethylamine, is a serotonin receptor agonist of the phenethylamine and 2C families. It was first synthesized and described by Daniel Trachsel 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 for the serotonin 5-HT2A receptor (Ki = 1.7nM) and to a much lesser extent for the serotonin 5-HT2C receptor (Ki = 75nM; 44-fold lower than for 5-HT2A). In terms of serotonin 5-HT2A receptor activation, its is 26nM and its is 40%. Hence, 2C-T-33 acts as a low-efficacy partial agonist of the serotonin 5-HT2A receptor. The drug shows higher affinity for the serotonin 5-HT2A receptor but much lower potency and efficacy in activating the receptor compared to 2C-T or 2C-B (which had values of Ki = 6.9–49nM, = 2.0–2.1nM, and = 75–92%). In contrast to most other 2C drugs and serotonergic psychedelics, 2C-T-33 appear ...
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2C (psychedelics)
2C (2C-''x'') is a general name for the family of psychedelic drug, psychedelic substituted phenethylamine, phenethylamines containing Methoxy, methoxy groups on the 2 and 5 carbon, positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolism, metabolically stable and longer acting compounds. Most of the currently known 2C compounds were first synthesized by Alexander Shulgin in the 1970s and 1980s and published in his book ''PiHKAL'' (''Phenethylamines i Have Known And Loved''). Shulgin also coined the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group. 2C-B is the most popular of the 2C drugs. Use The 2C drugs are oral administration, orally active, are used at oral doses of 6 to 150mg depending on the drug, and have duration of action, durations of 3 to 48hours depending on the drug. However, many have doses in the range of 10 to 60mg an ...
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2C Series
2C (2C-''x'') is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of a 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 compounds. Most of the currently known 2C compounds were first synthesized by Alexander Shulgin in the 1970s and 1980s and published in his book ''PiHKAL'' (''Phenethylamines i Have Known And Loved''). Shulgin also coined the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group. 2C-B is the most popular of the 2C drugs. Use The 2C drugs are orally active, are used at oral doses of 6 to 150mg depending on the drug, and have durations of 3 to 48hours depending on the drug. However, many have doses in the range of 10 to 60mg and durations in the range of 4 to 12hours. The 2C drugs produce psychedelic effects. Some, such as 2C-B, have al ...
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2C-Ph
2C-Ph, also known as 2C-BI-1 or as 2,5-dimethoxy-4-phenylphenethylamine, is a serotonin receptor modulator of the phenethylamine and 2C families that was developed by Daniel Trachsel and David E. Nichols and colleagues. The drug's affinity (Ki) for the rat serotonin 5-HT2A receptor was 778nM. It was said to be an antagonist of this receptor. In a subsequent study, 2C-Ph was a weak partial agonist of the human serotonin 5-HT2A receptor (Ki = 630nM, = 1,596nM, = 23%). The drug also shows affinity for the serotonin 5-HT1A, 5-HT2B, and 5-HT2C receptors, but did not activate the serotonin 5-HT2B receptor. In addition, it interacted with other monoamine receptors, with the monoamine transporters, and was a potent and high-efficacy partial agonist of the human trace amine-associated receptor 1 (TAAR1) ( = 580nM, = 82%). Besides 2C-Ph itself, a variety of derivatives of 2C-Ph with substituents on the 4-position phenyl ring have been synthesized and studied by Trachsel and colle ...
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Benzscaline
Benzscaline (BZ), also known as 4-benzyloxy-3,5-dimethoxyphenethylamine (4-BzlO-3,5-DMPEA), is a serotonin receptor agonist and possible serotonergic psychedelic of the phenethylamine and scaline families. It is a potent serotonin 5-HT2A receptor partial agonist, with an affinity (Ki) of 150nM, an activational potency () of 27nM, and an efficacy () of 77%. Its affinity and activational potency were 63- and 370-fold more potent than those of mescaline, respectively, and it was the most potent assessed mescaline analogue. In addition, benzscaline was more efficacious in activating the receptor than mescaline ( = 56% vs. 77%, respectively). Benzscaline does not activate the serotonin 5-HT2B receptor ( = >10,000nM), but does show affinity for the serotonin 5-HT2C receptor (Ki = 440nM). It also shows high affinity for the rat trace amine-associated receptor 1 (TAAR1) (Ki = 110nM), but not for the mouse TAAR1 (Ki = 2,400nM), and does not activate the human TAAR1 ( = >10,000nM). T ...
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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 psychoactive drug, psychoactive effects. This has been in a manner similar to that of the psychedelic chemist Alexander Shulgin, which has caused Trachsel to sometimes be referred to as the "German Shulgin". However, unlike Shulgin, Trachsel has distanced himself from any personal self-experimentation, self-experiments. According to Hamilton Morris and Nick Cozzi in mid-2023, Trachel's book ''Phenethylamine: von der Struktur zur Funktion'' (''Phenethylamines: From Structure to Function'') is in the process of being translated into English. It is being independently translated by the Alexander Shulgin Research Institute (ASRI), with tentative publication by Transform Press, and also by chemist David Carlson. Compounds Compounds that were first k ...
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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 the serotonin receptors. Non-selective agonists Serotonergic psychedelics such as tryptamines (e.g., psilocybin, psilocin, , 5-MeO-DMT, bufotenin), lysergamides (e.g., , ergine ()), phenethylamines (e.g., mescaline, 2C-B, 25I-NBOMe), and amphetamines (e.g., , ) are non-selective agonists of serotonin receptors. Their hallucinogenic effects are specifically mediated by activation of the 5-HT2A receptor. Drugs that increase extracellular serotonin levels such as serotonin reuptake inhibitors (e.g., fluoxetine, venlafaxine), serotonin releasing agents (e.g., fenfluramine, ), and monoamine oxidase inhibitors (e.g., phenelzine, moclobemide) are indirect non-selective serotonin receptor agonists. They are used variously as antidepressant ...
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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 lysergic acid diethylamide (LSD) and psilocybin consistently induce the HTR in rodents. Because of this, the HTR is widely employed in scientific research as an animal behavioral model of hallucinogen effects and in the discovery of new psychedelic drugs. The HTR is one of the only behavioral paradigms for assessment of psychedelic-like effects in animals, with the other most notable test being drug discrimination. However, the HTR is far less costly and time-consuming than drug discrimination and hence has become much more popular in recent years. Limitations of the HTR include the fact that various other drugs besides serotonin 5-HT2A receptor agonists, such as NMDA receptor antagonists and muscarinic acetylcholine receptor antagonists, ...
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Psychedelic Phenethylamines
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 hallucinogens or serotonergic hallucinogens, the term ''psychedelic'' is sometimes used more broadly to include various other types of hallucinogens as well, such as those which are atypical or adjacent to psychedelia like salvia and MDMA, respectively. Classic psychedelics generally cause specific psychological, visual, and auditory changes, and oftentimes a substantially altered state of consciousness. They have had the largest influence on science and culture, and include mescaline, LSD, psilocybin, and DMT. There are a large number of both naturally occurring and synthetic serotonergic psychedelics. Most psychedelic drugs fall into one of the three families of chemical compounds: tryptamines, phenethylamines, or lysergamides. They produ ...
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5-HT2A Agonists
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, memory, and physiological processes such as vomiting and vasoconstriction. In the CNS, serotonin regulates mood, appetite, and sleep. Most of the body's serotonin—about 90%—is synthesized in the gastrointestinal tract by enterochromaffin cells, where it regulates intestinal movements. It is also produced in smaller amounts in the brainstem's raphe nuclei, the skin's Merkel cells, pulmonary neuroendocrine cells, and taste receptor cells of the tongue. Once secreted, serotonin is taken up by platelets in the blood, which release it during clotting to promote vasoconstriction and platelet aggregation. Around 8% of the body's serotonin is stored in platelets, and 1–2% is found in the CNS. Serotonin acts as both a vasoconstrictor and v ...
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3C-BZ
3C-BZ, also known as 4-benzyloxy-3,5-dimethoxyamphetamine or as 3C-benzscaline, is a lesser-known psychedelic drug and a substituted amphetamine. 3C-BZ was first synthesized by Alexander Shulgin. Use and effects In Shulgin's book ''PiHKAL'', the dosage range is listed as 25–200 mg and the duration as 18–24 hours. According to anecdotal reports from the substance's entry in PiHKAL, 3C-BZ's effects can vary significantly, ranging from intensified emotions and strange dreams, to effects similar to those of LSD or TMA. Chemistry Synthesis 3C-BZ was originally synthesized by Alexander Shulgin starting from 5-methoxyeugenol (4-allyl-2,6-dimethoxyphenol) through a reaction with benzyl chloride to form the benzyloxy derivative of 5-methoxyeugenol. The obtained benzyl derivative was reacted with tetranitromethane to form 1- -(benzyloxy)-3,5-dimethoxyphenyl2-nitro-1-propene, from which 3C-BZ is obtained by reduction of the nitropropene with lithium aluminium hydride. Another p ...
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Aleph-6
Aleph, or Aleph-1, also known as DOT or para-DOT or as 4-methylthio-2,5-dimethoxyamphetamine, is a psychedelic drug of the amphetamine and DOx families. Effects Aleph was first synthesized by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. In his book ''PiHKAL'', Shulgin lists the dosage range as 5 to 10mg, with effects typically lasting for 6 to 8hours. Pharmacology Like many other psychedelics, Aleph is a partial agonist at the 5-HT2A receptor ( EC50 = 10 nM). It has weak MAO-A inhibitory activity with an IC50 of 5.2 μM. For reference, amphetamine has an IC50 of 11 μM and 4-methylthioamphetamine has a value of 0.2 μM. Homologues Aleph-2 ''Dosage'': 4–8 mg ''Duration'': 8–16 hours ''Effects'': Strong visuals '' 2C analog'': 2C-T-2 CAS number: 185562-00-9 SMILES: C1(=C(C=C(C(=C1)SCC)OC)CC(C)N)OC Aleph-4 ''Dosage'': 7–12 mg ''Duration'': 12–20 hours ''Effects'': "''profound and deep learni ...
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