5-MeO-NMT
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5-MeO-NMT
5-MeO-NMT (5-methoxy-''N''-methyltryptamine) is an organic chemical compound, being the 5-methoxy analog (chemistry), analog of N-Methyltryptamine, ''N''-methyltryptamine (NMT). It was first isolated from ''Phalaris arundinacea'' (reed canary grass). It has also been synthesized by Alexander Shulgin and reported in his book ''TiHKAL''. Like other members of the ''N''-methyltryptamine family of compounds, 5-MeO-NMT is believed to produce few or no psychedelic effects, although very little data exists about its pharmacological properties or toxicity. Legal Status In the U.S. this substance is a schedule 1 isomer of Bufotenin. See also * Tryptamine * Dimethyltryptamine * Psychedelics, dissociatives and deliriants References

Tryptamines {{Psychoactive-stub ...
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Phalaris Arundinacea
''Phalaris arundinacea'', or reed canary grass, is a tall, perennial bunchgrass that commonly forms extensive single-species stands along the margins of lakes and streams and in wet open areas, with a wide distribution in Europe, Asia, northern Africa and North America. Other common names for the plant include gardener's-garters in English, ''alpiste roseau'' in French, ''Rohrglanzgras'' in German, ''kusa-yoshi'' in Japanese, ''caniço-malhado'' in Portuguese, and ''hierba cinta'' and ''pasto cinto'' in Spanish.''Phalaris arundinacea''.
USDA NRCS Plant Guide.


Description

The stems can reach in height.Waggy, Melissa, A. 2010.

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TiHKAL
''TIHKAL: The Continuation'' is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to '' PIHKAL: A Chemical Love Story'', ''TIHKAL'' is an acronym that stands for "Tryptamines I Have Known and Loved". Content ''TIHKAL'', much like its predecessor ''PIHKAL'', is divided into two parts. The first part, for which all rights are reserved, begins with a fictionalized autobiography, picking up where the similar section of ''PIHKAL'' left off; it then continues with a collection of essays on topics ranging from psychotherapy and the Jungian mind to the prevalence of DMT in nature, ayahuasca and the War on Drugs. The second part of ''TIHKAL'', which may be conditionally distributed for non-commercial reproduction (see external links An internal link is a type of hyperlink on a web page to another page or resource, such as an image or document, on the same website or domain. Hyperlinks are considered eit ...
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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 nucleosi ...
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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 il ...
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N-Methyltryptamine
''N''-Methyltryptamine (NMT) is a member of the substituted tryptamine chemical class and a natural product which is biosynthesized in the human body from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine ''N''-methyltransferase. It is a common component in human urine. NMT is an alkaloid derived from L-tryptophan that has been found in the bark, shoots and leaves of several plant genera, including ''Virola'', ''Acacia'', ''Mimosa'', and ''Desmanthus''—often together with the related compounds ''N'',''N''-dimethyltryptamine (DMT) and 5-methoxy-''N'',''N''-dimethyltryptamine (5-MeO-DMT). Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.Foye's principles of medicinal chemistry By William O. Foye, Thomas L. Lemke, David A. Williams However, it may become active upon combination with a MAOA inhibitor (MAOI). By vaporization NMT shows activity at 50–100 mg, with a duration o ...
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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 compounds of t ...
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Bufotenin
Bufotenin (5-HO-DMT, bufotenine) is a tryptamine derivative - more specifically, a DMT derivative - related to the neurotransmitter serotonin. It is an alkaloid found in some species of toads (especially the skin), mushrooms and plants. The name bufotenin originates from the toad genus ''Bufo'', which includes several species of psychoactive toads, most notably ''Incilius alvarius'', that secrete bufotoxins from their parotoid glands. Bufotenin is similar in chemical structure to the psychedelics psilocin (4-HO-DMT), 5-MeO-DMT, and DMT, chemicals which also occur in some of the same fungus, plant, and animal species as bufotenin. Nomenclature Bufotenin (bufotenine) is also known by the chemical names 5-hydroxy-''N'',''N''-dimethyltryptamine (5-HO-DMT), ''N'',''N''-dimethyl-5-hydroxytryptamine, dimethyl serotonin, and mappine. History Bufotenin was isolated from toad skin, and named by the Austrian chemist Handovsky at the University of Prague during World War I. The struct ...
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Tryptamine
Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan. The chemical structure is defined by an indole ─ a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the first one being the heterocyclic nitrogen). The structure of tryptamine is a shared feature of certain aminergic neuromodulators including melatonin, serotonin, bufotenin and psychedelic derivatives such as dimethyltryptamine (DMT), psilocybin, psilocin and others. Tryptamine has been shown to activate trace amine-associated receptors expressed in the mammalian brain, and regulates the activity of dopaminergic, serotonergic and glutamatergic systems. In the human gut, symbiotic bacteria convert dietary tryptophan to tryptamine, which activates 5-HT4 receptors and regulates gastrointestinal motility. Multiple tryptamine-derived drugs have been developed to treat migraines, while trace amine-associated receptors are being explored as a ...
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Dimethyltryptamine
''N'',''N''-Dimethyltryptamine (DMT or ''N'',''N''-DMT, SPL026) is a substituted tryptamine that occurs in many plants and animals, including human beings, and which is both a derivative and a structural analog of tryptamine. It is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen. DMT has a rapid onset, intense effects, and a relatively short duration of action. For those reasons, DMT was known as the "business trip" during the 1960s in the United States, as a user could access the full depth of a psychedelic experience in considerably less time than with other substances such as LSD or psilocybin mushrooms. DMT can be inhaled, ingested, or injected and its effects depend on the dose, as well as the mode of administration. When inhaled or injected, the effects last a short period of time: about five to 15 minutes. Effects can last three hours or more when orally ingested along with a monoamine oxidase inhibitor (MAOI), such as ...
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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 Gle ...
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