Thioproscaline
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Thioproscaline
Thioproscaline, or 3,5-dimethoxy-4-propyl thio phenethylamine, is a lesser-known psychedelic drug. It is the 4-propyl thio analog of mescaline. Thioproscaline was first synthesized by Alexander Shulgin. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'', the dosage range is listed as 20–25 mg, and the duration listed as 10–15 hours. Thioproscaline causes closed-eye visuals, slight open-eye visuals, and a body load. Very little data exists about the pharmacological properties, metabolism, and toxicity of thioproscaline. See also * Phenethylamine * Psychedelics, dissociatives and deliriants * Mescaline * Proscaline Proscaline (4-propoxy-3,5-DMPEA) is a psychedelic and hallucinogenic drug. It has structural properties similar to the drugs mescaline, isoproscaline, and escaline. In '' PiHKAL'', Alexander Shulgin reports that a dose of 30–60 mg produ ... * Thiomescaline External links Thioproscaline entry in ''PiHKAL''Thioproscaline entry ...
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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 as an electron-donating group, but as an electron-withdrawing group if at the ''meta'' position. At the ''ortho'' position, steric effects are likely to cause a significant alteration in the Hammett equation prediction which otherwise follows the same trend as that of the ''para'' position. Occurrence The simplest of methoxy compounds are methanol and dimethyl ether. Other methoxy ethers include anisole and vanillin. Many alkoxides contain methoxy groups, e.g. tetramethyl orthosilicate and titanium methoxide. Such compounds are often classified as methoxides. Esters with a methoxy group can be referred to as methyl esters, and the —COOCH3 substituent is called a methoxycarbonyl. Biosynthesis In nature, methoxy groups are found on nucl ...
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Propyl
In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula for the linear form. This substituent form is obtained by removing one hydrogen atom attached to the terminal carbon of propane. A propyl substituent is often represented in organic chemistry with the symbol Pr (not to be confused with the element praseodymium). An isomeric form of propyl is obtained by moving the point of attachment from a terminal carbon atom to the central carbon atom, named 1-methylethyl or isopropyl. To maintain four substituents on each carbon atom, one hydrogen atom has to be moved from the middle carbon atom to the carbon atom which served as attachment point in the ''n''-propyl variant, written as . Linear propyl is sometimes termed normal and hence written with a prefix ''n''- (i.e., ''n-''propyl), as the absence of the prefix ''n''- does not indicate which attachment point is chosen, i.e. absence of prefix does not automatically exclude the possibility of it being ...
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Thio-
The prefix thio-, when applied to a chemical, such as an ion, means that an oxygen atom in the compound has been replaced by a sulfur atom. This term is often used in organic chemistry. For example, from the word ''ether,'' referring to an oxygen-containing compound having the general chemical structure , where R and R′ are organic functional groups and O is an oxygen atom, comes the word ''thioether'', which refers to an analogous compound with the general structure , where S is a sulfur atom covalently bonded to two organic groups. A chemical reaction involving the replacement of oxygen to sulfur is called thionation or thiation. Thio- can be prefixed with ''di-'' and ''tri-'' in chemical nomenclature. The word derives (which occurs in Greek epic poetry as grc, θέ(ϝ)ειον, théweion, label=none and may come from the same root as Latin (Indo-European ''dh-w'') and may have originally meant " fumigation substance".) Examples * Thioamide * Thiocyanate * Thioether * ...
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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 amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation. Phenethylamine is sold as a dietary supplement for purported mood and weight loss-related therapeutic benefits; however, in orally ingested phenethylamine, a significant amount is metabolized in the small intestine by monoa ...
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Psychedelics, Dissociatives And Deliriants
Hallucinogens are a large, diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mood, and perception as well as other changes. Most hallucinogens can be categorized as either being psychedelics, dissociatives, or deliriants. However, certain hallucinogens such as Fly agaric as well as other gabaergic hallucinogenics are more often considered to technically be hypnotics, therefore indicating another separate subcategory of drugs which can substantially alter visual perception. Etymology The word ''hallucinogen'' is derived from the word ''hallucination''. The term ''hallucinate'' dates back to around 1595–1605, and is derived from the Latin ''hallūcinātus'', the past participle of ''(h)allūcināri'', meaning "to wander in the mind." Characteristics Leo Hollister gave five criteria for classifying a drug as hallucinogenic.Glennon RA. Classical drugs: an introductory overview. In Lin GC and ...
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Analog (chemistry)
A structural analog (analogue in modern traditional English; Commonwealth English), also known as a chemical analog or simply an analog, is a compound having a structure similar to that of another compound, but differing from it in respect to a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced with other atoms, groups, or substructures. A structural analog can be imagined to be formed, at least theoretically, from the other compound. Structural analogs are often isoelectronic. Despite a high chemical similarity, structural analogs are not necessarily functional analogs and can have very different physical, chemical, biochemical, or pharmacological properties. In drug discovery, either a large series of structural analogs of an initial lead compound are created and tested as part of a structure–activity relationship study or a database is screened for structural analogs of a lead compound. Chemical analogues of i ...
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Mescaline
Mescaline or mescalin (3,4,5-trimethoxyphenethylamine) is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. Biological sources It occurs naturally in several species of cacti. It is also found in small amounts in certain members of the bean family, Fabaceae, including '' Acacia berlandieri''. However those claims concerning ''Acacia'' species have been challenged and have been unsupported in any additional analysis. History and use Peyote has been used for at least 5,700 years by Indigenous peoples of the Americas in Mexico. Europeans noted use of peyote in Native American religious ceremonies upon early contact, notably by the Huichols in Mexico. Other mescaline-containing cacti such as the San Pedro have a long history of use in South America, from Peru to Ecuador. While religious and ceremonial peyote use was widespread in the Aztec empire and nor ...
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Alexander Shulgin
Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamphetamine (MDMA, commonly known as "ecstasy") to psychologists in the late 1970s for psychopharmaceutical use and for the discovery, synthesis and personal bioassay of over 230 psychoactive compounds for their psychedelic and entactogenic potential. In 1991 and 1997, he and his wife Ann Shulgin compiled the books '' PiHKAL'' and '' TiHKAL'' (standing for '' Phenethylamines'' and ''Tryptamines I Have Known And Loved''), from notebooks that extensively described their work and personal experiences with these two classes of psychoactive drugs. Shulgin performed seminal work into the descriptive synthesis of many of these compounds. Some of Shulgin's noteworthy discoveries include compounds of the 2C* family (such as 2C-B) and compou ...
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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 amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation. Phenethylamine is sold as a dietary supplement for purported mood and weight loss-related therapeutic benefits; however, in orally ingested phenethylamine, a significant amount is metabolized in the small intestine by monoa ...
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Mescaline
Mescaline or mescalin (3,4,5-trimethoxyphenethylamine) is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. Biological sources It occurs naturally in several species of cacti. It is also found in small amounts in certain members of the bean family, Fabaceae, including '' Acacia berlandieri''. However those claims concerning ''Acacia'' species have been challenged and have been unsupported in any additional analysis. History and use Peyote has been used for at least 5,700 years by Indigenous peoples of the Americas in Mexico. Europeans noted use of peyote in Native American religious ceremonies upon early contact, notably by the Huichols in Mexico. Other mescaline-containing cacti such as the San Pedro have a long history of use in South America, from Peru to Ecuador. While religious and ceremonial peyote use was widespread in the Aztec empire and nor ...
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Proscaline
Proscaline (4-propoxy-3,5-DMPEA) is a psychedelic and hallucinogenic drug. It has structural properties similar to the drugs mescaline, isoproscaline, and escaline. In '' PiHKAL'', Alexander Shulgin reports that a dose of 30–60 mg produces effects lasting 8–12 hours. Chemistry Proscaline is in a class of compounds commonly known as phenethylamines, and is the 4-propoxy homolog of mescaline. The full name of the chemical is 4-propoxy-3,5-dimethoxyphenethylamine. Legality Proscaline is a Class A controlled substance in the UK. Proscaline is unscheduled and unregulated in the United States, but it could be considered an analog of a schedule I drug, mescaline, under the Federal Analog Act and thus be subject to the same control measures and penalties for possession and manufacture as a Schedule I drug. See also * Substituted phenethylamine * Allylescaline * 3C-P * Mescaline Mescaline or mescalin (3,4,5-trimethoxyphenethylamine) is a naturally occurring psyched ...
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