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2,5-Dimethoxy-4-hexylamphetamine
2,5-Dimethoxy-4-hexylamphetamine (DOHx or DOHE) is a non-hallucinogenic serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families. Pharmacology DOHx has shown the highest affinity for the serotonin 5-HT2A and 5-HT2C receptors of any other assessed DOx drug in multiple studies. In one study, its affinities for the human serotonin 5-HT2 receptors were 0.1nM for the 5-HT2A receptor, 30nM for the 5-HT2B receptor, and 0.7nM for 5-HT2C receptor. In the case of the serotonin 5-HT2A receptor, this was 6- to 14-fold higher than DOB, DOI, and DOC and was 9-fold higher than DOPR. In another study, DOHx showed 25-fold higher affinity for the serotonin 5-HT2A receptor than DOM or DOET, 23- to 28-fold higher affinity than DOPR and DOBU, and 2.8-fold higher affinity than DOAM. Conversely, it showed only slightly higher or roughly the same affinity for the receptor relative to DOCT (2.5nM vs. 3.0nM, respectively). In contrast to many other DOx drugs, DOHx, as well a ...
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4-substituted 2,5-dimethoxyamphetamine
4-Substituted-2,5-dimethoxyamphetamines (DO''x'') is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. They are 4-substituted derivatives of 2,5-dimethoxyamphetamine (2,5-DMA, DOH) and are structurally related to the naturally occurring phenethylamine psychedelic mescaline. The most well-known DOx drugs are DOM, DOI, DOB, DOET, and DOC. DOI is widely used in scientific research. DOM has been used as a recreational drug, while DOET was an experimental pharmaceutical drug. Most compounds of this class are potent and long-lasting psychedelic drugs, and act as selective 5-HT2A, 5-HT2B, and 5-HT2C receptor agonists. A few bulkier derivatives such as DOAM have similarly high affinity for 5-HT2 receptors but have reduced activational efficacy and do not produce psychedelic effects. DOI has been found to have ...
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DOAM (drug)
2,5-Dimethoxy-4-amylamphetamine (DOAM), also known as 2,5-dimethoxy-4-pentylamphetamine, is a lesser-known serotonin receptor agonist and serotonergic psychedelic of the amphetamine and DOx families. Effects DOAM was first synthesized by Alexander Shulgin. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'', the minimum dosage is listed as 10mg orally and the duration is unknown. DOAM was reported to produce a bare threshold and tenseness. In other publications however, DOAM has been said to produce threshold effects at 5 to 10mg orally and to be hallucinogenic at a dose of 40mg, with about 10-fold higher potency than mescaline. In any case, it shows far lower psychedelic potency than other DOx drugs such as DOM. No qualitative description of its effects at hallucinogenic doses is available. Pharmacology DOAM has been found to be a moderate-efficacy partial agonist of the serotonin 5-HT2A receptor. It also shows lower affinity for the serotonin 5-HT2C receptor, ...
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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, 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 vas ...
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DOPR (drug)
2,5-Dimethoxy-4-propylamphetamine (DOPR) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It was first synthesized by Alexander Shulgin, and was described in his book ''PiHKAL'' (''Phenethylamines i Have Known And Loved''). Very little data exists about the pharmacological properties, metabolism, and toxicity of DOPR. Use and effects According to Alexander Shulgin in ''PiHKAL'', the dosage of DOPR is 2.5 to 5mg and its duration is 20 to 30hours. He described DOPR as a "heavy duty psychedelic", complete with alterations of the thought process and visual distortion. Pharmacology Pharmacodynamics DOPR acts as an agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. It has very weak affinity for the serotonin 5-HT1 receptor. It produces the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents. As with many other psychedelics, DOPR shows an inverted U-shaped dose–re ...
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Side Chain
In organic chemistry and biochemistry, a side chain is a substituent, chemical group that is attached to a core part of the molecule called the "main chain" or backbone chain, backbone. The side chain is a hydrocarbon branching element of a molecule that is attached to a larger hydrocarbon backbone. It is one factor in determining a molecule's properties and reactivity. A side chain is also known as a pendant chain, but a pendant group (side group) has a different definition. Conventions The placeholder R is often used as a generic placeholder for alkyl (saturated hydrocarbon) group side chains in structural formulae. To indicate other non-carbon groups in structure diagrams, X, Y, or Z are often used. History The ''R'' symbol was introduced by 19th-century French chemist Charles Frédéric Gerhardt, who advocated its adoption on the grounds that it would be widely recognizable and intelligible given its correspondence in multiple European languages to the initial letter of "r ...
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Chemical Substituent
In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. The suffix ''-yl'' is used when naming organic compounds that contain a single bond replacing one hydrogen; ''-ylidene'' and ''-ylidyne'' are used with double bonds and triple bonds, respectively. In addition, when naming hydrocarbons that contain a substituent, positional numbers are used to indicate which carbon atom the substituent attaches to when such information is needed to distinguish between isomers. Substituents can be a combination of the inductive effect and the mesomeric effect. Such effects are also described as electron-rich and electron withdrawing. Additional steric effects result from the volume occupied by a substituent. The phrases ''most-substituted'' and ''least-substituted'' are frequently used to describe or compare molecules that are products of a chemical reaction. In this terminology, methane is ...
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Hexyl Group
In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula . Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula . Related concepts Alkylation is the addition of alkyl groups to molecules, often by alkylating agents such as alkyl halides. Alkylating antineoplastic agents are a class of compounds that are used to treat cancer. In such case, the term alkyl is used loosely. For example, nitrogen mustards are well-known alkylating agents, but they are not simple hydrocarbons. In chemistry, alkyl is a group, a substituent, that is attached to other molecular fragments. For e ...
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DOBU (drug)
2,5-Dimethoxy-4-butylamphetamine (DOBU) is a lesser-known serotonin receptor agonist and serotonergic psychedelic of the amphetamine and DOx families. Effects DOBU was first synthesized by Alexander Shulgin. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'' and other publications, he and colleagues stated that doses of 1 to 3mg orally produced clear threshold effects and it was active at a dosage of slightly more than twice that of DOM. It was stated that 10mg DOBU was required to produce hallucinogenic effects. The drug's duration was listed as "very long". There was limited investigation on the qualitative effects of DOAM. However, in ''PiHKAL'', at the assessed doses of 2.2mg and 2.8mg, it was described as producing paresthesia and difficulty sleeping with few other effects. Pharmacology Compared to shorter chain homologues such as DOM, DOET, and DOPR which are all potent hallucinogens, DOBU has an even higher serotonin 5-HT2 receptor affinity. It has be ...
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Alkyl Group
In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a Ring (chemistry), ring and has the general formula . Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula . Related concepts Alkylation is the addition of alkyl groups to molecules, often by alkylating agents such as Haloalkane, alkyl halides. Alkylating antineoplastic agents are a class of compounds that are used to treat cancer. In such case, the term alkyl is used loosely. For example, nitrogen mustards are well-known alkylating agents, but they are not simple hydrocarbons. In chemistry, alkyl is a group, a substituent, that is attached to ot ...
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Silent Antagonist
A receptor antagonist is a type of receptor ligand or drug that blocks or dampens a biological response by binding to and blocking a receptor rather than activating it like an agonist. Antagonist drugs interfere in the natural operation of receptor proteins.Pharmacology Guide: In vitro pharmacology: concentration-response curves
." '' GlaxoWellcome.'' Retrieved on December 6, 2007.
They are sometimes called blockers; examples include s,

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 it is tested with novel drugs to see if the novel drugs are experienced as similar to the training drug. In essence, the drug discrimination paradigm has the subject "tell" the experimenter "I think you gave me the training drug" or "I don't think you gave me anything". The discriminative stimulus properties of drugs are believed to reflect their subjective effects. When partial or full stimulus generalization of a test drug to a training drug occurs, the test drug can be assumed to have effects that are subjectively similar to those of the training drug. Drug discrimination tests are usually performed in animals, but have also been conducted in humans. Drug discrimination assays have been employed to assess whether drugs have stimulant- ...
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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 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 pro ...
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