5-Ethoxy-DMT
Encyclopedia
5-Ethoxy-N,N-dimethyltryptamine (5-EtO-DMT, O-Ethylbufotenine) is a tryptamine
derivative, which has been previously synthesised as a chemical intermediate, but has not been studied to determine its pharmacology. Some closely related compounds have been studied and found to act as agonist
s at the 5-HT1A
and 5-HT1D
serotonin
receptors
, with increasing selectivity for 5-HT1D as the 5-alkoxy chain is lengthened, but generally reduced affinity with N,N-dialkylation. The affinity of larger 5-position substituted N,N-dialkyltryptamines at the 5-HT2 receptor
subtypes has in most cases not been studied, but the widespread recreational use of N,N-dialkylated 5-methoxytryptamine
derivatives including 5-MeO-DMT
, 5-MeO-MiPT
and 5-MeO-DiPT
has led to concern that the 5-ethoxy homologues of these drugs could emerge as novel designer drug
s, and consequently not only 5-EtO-DMT but also other derivatives including 5-EtO-DET, 5-EtO-DPT, 5-EtO-DiPT, 5-EtO-DALT, 5-EtO-MPT, 5-EtO-MiPT, 5-EtO-EiPT, 5-EtO-MET and 5-EtO-EPT, were synthesised as analytical standards
in order to facilitate future research into these compounds.
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...
derivative, which has been previously synthesised as a chemical intermediate, but has not been studied to determine its pharmacology. Some closely related compounds have been studied and found to act as agonist
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...
s at the 5-HT1A
5-HT1A receptor
The 5-HT1A receptor is a subtype of 5-HT receptor that binds the endogenous neurotransmitter serotonin . It is a G protein-coupled receptor that is coupled to Gi/Go and mediates inhibitory neurotransmission...
and 5-HT1D
5-HT1D receptor
5-hydroxytryptamine receptor 1D, also known as HTR1D, is a 5-HT receptor, but also denotes the human gene encoding it. 5-HT1D acts on the central nervous system, and affects locomotion and anxiety...
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...
receptors
Receptor (biochemistry)
In biochemistry, a receptor is a molecule found on the surface of a cell, which receives specific chemical signals from neighbouring cells or the wider environment within an organism...
, with increasing selectivity for 5-HT1D as the 5-alkoxy chain is lengthened, but generally reduced affinity with N,N-dialkylation. The affinity of larger 5-position substituted N,N-dialkyltryptamines at the 5-HT2 receptor
5-HT2 receptor
The 5-HT2 receptors are a subfamily of 5-HT receptors that bind the endogenous neurotransmitter serotonin . The 5-HT2 subfamily consists of three G protein-coupled receptors which are coupled to Gq/G11 and mediate excitatory neurotransmission, including 5-HT2A, 5-HT2B, and 5-HT2C...
subtypes has in most cases not been studied, but the widespread recreational use of N,N-dialkylated 5-methoxytryptamine
5-Methoxytryptamine
5-Methoxytryptamine , also known as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. 5-MT has been shown to occur naturally in the body in low levels. It is biosynthesized via the deacetylation of melatonin in the pineal gland.5-MT acts as a...
derivatives including 5-MeO-DMT
5-MeO-DMT
5-MeO-DMT is a powerful psychedelic tryptamine. It is found in a wide variety of plant and psychoactive toad species and, like its close relatives DMT and bufotenin , it has been used as an entheogen by South American shamans for thousands of years.-Chemistry:5-MeO-DMT was first synthesized in...
, 5-MeO-MiPT
5-MeO-MIPT
5-MeO-MiPT is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT...
and 5-MeO-DiPT
5-MeO-DIPT
5-methoxy-diisopropyltryptamine is a tryptamine psychedelic used as a recreational drug under the street names "foxy" and "foxy methoxy". 5-MeO-DiPT is orally active, and dosages between 6–20 mg are commonly reported. Many users note an unpleasant body load accompanies higher dosages...
has led to concern that the 5-ethoxy homologues of these drugs could emerge as novel designer drug
Designer drug
Designer drug is a term used to describe drugs that are created to get around existing drug laws, usually by preparing analogs or derivatives of existing drugs by modifying their chemical structure to varying degrees, or less commonly by finding drugs with entirely different chemical structures...
s, and consequently not only 5-EtO-DMT but also other derivatives including 5-EtO-DET, 5-EtO-DPT, 5-EtO-DiPT, 5-EtO-DALT, 5-EtO-MPT, 5-EtO-MiPT, 5-EtO-EiPT, 5-EtO-MET and 5-EtO-EPT, were synthesised as analytical standards
Analytical chemistry
Analytical chemistry is the study of the separation, identification, and quantification of the chemical components of natural and artificial materials. Qualitative analysis gives an indication of the identity of the chemical species in the sample and quantitative analysis determines the amount of...
in order to facilitate future research into these compounds.