Diethyltryptamine
Encyclopedia
DET, also known under its chemical name N,N-diethyltryptamine and as T-9, is a psychedelic drug
closely related to DMT
and 4-HO-DET
. However, despite its structural similarity
to DMT it is active orally around 50–100 mg without the aid of MAO inhibitors
lasting about 2–4 hours.
hallucinogen N,N-Dimethyltryptamine or DMT. DET is sometimes preferred over DMT because it can be taken orally whereas DMT cannot. This is because the enzyme monoamine oxidase
degrades DMT into an inactive compound before it is absorbed. To overcome this, it must be administered in a different manner, i.e. intravenously, intramuscularly, by inhalation, by insufflation, or rectally. Because DET has ethyl groups attached to its nitrogen atom monoamine oxidase is unable to degrade it. This is true for many other tryptamines with larger nitrogen substitutents.
agonism
, much like other classic psychedelics.
compound with no known natural sources
it has been used with mycelium
of Psilocybe cubensis
to produce the synthetic chemicals 4-PO-DET (Ethocybin) and 4-HO-DET (Ethocin)
, as opposed the naturally occurring 4-PO-DMT (Psilocybin) and 4-HO-DMT (Psilocin). Isolation of the alkaloids resulted in 3.3% 4-HO-DET and 0.01-0.8% 4-PO-DET.
properties. Researchers theorized that abnormal metabolites of endogenous chemicals such as tryptamine
, serotonin
, and tryptophan
could be the explanation for mental disorders as schizophrenia
, or psychosis
. With the progression of science and pharmacological understanding this belief has been dismissed by most researchers.
Psychedelic tryptamines
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
closely related to DMT
Dimethyltryptamine
N,N-Dimethyltryptamine is a naturally occurring psychedelic compound of the tryptamine family. DMT is found in several plants, and also in trace amounts in humans and other mammals, where it is originally derived from the essential amino acid tryptophan, and ultimately produced by the enzyme INMT...
and 4-HO-DET
4-HO-DET
4-HO-DET, also known as 4-hydroxy-diethyl-tryptamine, CZ-74, or ethocin, is a hallucinogenic drug and psychedelic compound of moderate duration. 4-HO-DET is a substituted tryptamine, structurally related to psilocin and 4-HO-DIPT.-Analogs:...
. However, despite its structural similarity
Analog (chemistry)
In chemistry, a structural analog , also known as chemical analog or simply analog, is a compound having a structure similar to that of another one, but differing from it in respect of a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced...
to DMT it is active orally around 50–100 mg without the aid of MAO inhibitors
Monoamine oxidase inhibitor
Monoamine oxidase inhibitors are a class of antidepressant drugs prescribed for the treatment of depression. They are particularly effective in treating atypical depression....
lasting about 2–4 hours.
Chemistry
DET is an analogue of the common tryptamineTryptamine
Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived...
hallucinogen N,N-Dimethyltryptamine or DMT. DET is sometimes preferred over DMT because it can be taken orally whereas DMT cannot. This is because the enzyme monoamine oxidase
Monoamine oxidase
L-Monoamine oxidases are a family of enzymes that catalyze the oxidation of monoamines. They are found bound to the outer membrane of mitochondria in most cell types in the body. The enzyme was originally discovered by Mary Bernheim in the liver and was named tyramine oxidase...
degrades DMT into an inactive compound before it is absorbed. To overcome this, it must be administered in a different manner, i.e. intravenously, intramuscularly, by inhalation, by insufflation, or rectally. Because DET has ethyl groups attached to its nitrogen atom monoamine oxidase is unable to degrade it. This is true for many other tryptamines with larger nitrogen substitutents.
Pharmacology
The mechanism of action is thought to be serotonin receptor5-HT receptor
The serotonin receptors, also known as 5-hydroxytryptamine receptors or 5-HT receptors, are a group of G protein-coupled receptors and ligand-gated ion channels found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory neurotransmission...
agonism
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
, much like other classic psychedelics.
Biochemistry
Though DET is a syntheticChemical synthesis
In chemistry, chemical synthesis is purposeful execution of chemical reactions to get a product, or several products. This happens by physical and chemical manipulations usually involving one or more reactions...
compound with no known natural sources
Psychedelic plants
A list of plants that are used for psychedelic drugs. Some of them have been used for thousands of years for religious purposes. The plants are listed according to the substances they contain.-THC:Cannabis is a popular psychedelic plant...
it has been used with mycelium
Mycelium
thumb|right|Fungal myceliaMycelium is the vegetative part of a fungus, consisting of a mass of branching, thread-like hyphae. The mass of hyphae is sometimes called shiro, especially within the fairy ring fungi. Fungal colonies composed of mycelia are found in soil and on or within many other...
of Psilocybe cubensis
Psilocybe cubensis
Psilocybe cubensis is a species of psychedelic mushroom whose principal active compounds are psilocybin and psilocin. Commonly called Boomers, Cubes or Gold Caps, it belongs to the Strophariaceae family of fungi and was previously known as Stropharia cubensis.-Taxonomy and naming:The species was...
to produce the synthetic chemicals 4-PO-DET (Ethocybin) and 4-HO-DET (Ethocin)
4-HO-DET
4-HO-DET, also known as 4-hydroxy-diethyl-tryptamine, CZ-74, or ethocin, is a hallucinogenic drug and psychedelic compound of moderate duration. 4-HO-DET is a substituted tryptamine, structurally related to psilocin and 4-HO-DIPT.-Analogs:...
, as opposed the naturally occurring 4-PO-DMT (Psilocybin) and 4-HO-DMT (Psilocin). Isolation of the alkaloids resulted in 3.3% 4-HO-DET and 0.01-0.8% 4-PO-DET.
Psychosis model
Early studies of DET, as well as other psychedelics, mainly focused on the believed psychotomimeticPsychotomimetic
A drug with psychotomimetic actions mimics the symptoms of psychosis, including delusions and/or delirium, as opposed to just hallucinations. Some drugs of the opioid class have psychotomimetic effects, such as pentazocine and butorphanol....
properties. Researchers theorized that abnormal metabolites of endogenous chemicals such as tryptamine
Tryptamine
Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived...
, serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
, and tryptophan
Tryptophan
Tryptophan is one of the 20 standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG...
could be the explanation for mental disorders as schizophrenia
Schizophrenia
Schizophrenia is a mental disorder characterized by a disintegration of thought processes and of emotional responsiveness. It most commonly manifests itself as auditory hallucinations, paranoid or bizarre delusions, or disorganized speech and thinking, and it is accompanied by significant social...
, or psychosis
Psychosis
Psychosis means abnormal condition of the mind, and is a generic psychiatric term for a mental state often described as involving a "loss of contact with reality"...
. With the progression of science and pharmacological understanding this belief has been dismissed by most researchers.
See also
- TiHKALTiHKALTiHKAL: 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...
- 5-MeO-DET5-MeO-DET5-MeO-DET or 5-methoxy-N,N-diethyltryptamine is a hallucinogenic tryptamine.-Effects:Low dosages are reported to produce a relaxing body high and mild entheogenic effects. Shulgin reports in TiHKAL that higher dosages can produce very unpleasant reactions.-External links:**...
- 4-PO-DET (Ethocybin)EthocybinEthocybin is a homologue of the mushroom alkaloid psilocybin, and a semi-synthetic psychedelic alkaloid of the tryptamine family...
Psychedelic tryptamines