Summary
α-Ethyltryptamine (αET, AET), also referred to as etryptamine (INN, BAN, USAN), is a member of the tryptamine class of compounds, exhibiting psychedelic, stimulant, and entactogenic properties. During the 1960s, it was initially created and introduced as an antidepressant by Upjohn, bearing the brand name Monase.
| Identifiers | |
|---|---|
| IUPAC name | |
| CAS Number | 2235-90-7 118-68-3 |
|---|---|
| PubChem CID | 8367 |
| PubChem SID | 46507084 |
| DrugBank | DB01546 |
| ChemSpider | 8064 |
| UNII | GR181O3R32 |
| KEGG | D04092 |
| ChEBI | CHEBI:134838 |
| ChEMBL | ChEMBL1619758 |
| CompTox Dashboard (EPA) | DTXSID1046764 |
| Chemical and physical data | |
| Formula | C12H16N2 |
| Molar mass | 188.274 g·mol−1 |
History
Initially, it was thought that α-ethyltryptamine primarily influenced its effects through monoamine oxidase inhibition. In the 1960s, Upjohn, a chemical company in the United States, developed α-ethyltryptamine as an antidepressant called Monase. However, it was withdrawn from consideration for commercial use due to cases of idiosyncratic agranulocytosis.
During the 1980s, α-ethyltryptamine gained modest popularity as a recreational designer drug. Later, in the United States, it was classified as a Schedule I substance in 1993, rendering it illegal.
Pharmacology
α-Ethyltryptamine is both structurally and pharmacologically linked to α-methyltryptamine (αMT). Interestingly, its central stimulant effects are not primarily attributed to its function as a monoamine oxidase inhibitor (MAOI). Instead, these effects are thought to be associated with its structural resemblance to indolic psychedelics. Compared to αMT, α-ethyltryptamine is characterized by being less stimulating and hallucinogenic. Its products are somewhat akin to entactogens like MDMA, often referred to as “Ecstasy.”
Like αMT, α-ethyltryptamine functions as a serotonin, norepinephrine, and dopamine-releasing agent, with serotonin being the primary neurotransmitter affected. Additionally, it acts as a non-selective serotonin receptor agonist. In a 1991 study involving rat subjects, there was evidence to suggest that α-ethyltryptamine might induce serotonergic neurotoxicity similar to that of MDMA. As is the case with various other serotonin-releasing agents, excessive doses or combinations with drugs like other MAOIs can lead to injury.
FAQ
- What is α-Ethyltryptamine (αET)?
- α-Ethyltryptamine, also known as αET or etryptamine, is a drug belonging to the tryptamine class. It has psychedelic, stimulant, and entactogenic properties. In the 1960s, it was initially developed and marketed as an antidepressant under the brand name Monase by Upjohn, a pharmaceutical company.
- Why was α-Ethyltryptamine developed as an antidepressant?
- α-Ethyltryptamine was initially intended to be used as an antidepressant due to its potential to influence mood and mental well-being. However, its development for this purpose was discontinued because of cases of idiosyncratic agranulocytosis.
- What happened to its commercial use as an antidepressant?
- Due to the occurrence of idiosyncratic agranulocytosis (a condition characterized by a significant decrease in white blood cells), the development of α-Ethyltryptamine as an antidepressant was halted, and it was not pursued for commercial use.
- Has α-Ethyltryptamine been used recreationally?
- Yes, α-Ethyltryptamine gained some popularity as a recreational designer drug during the 1980s. Its use, however, led to it being classified as a Schedule I controlled substance in the United States in 1993.
- How does α-Ethyltryptamine compare to other similar substances like α-methyltryptamine (αMT) and MDMA?
- α-Ethyltryptamine is structurally and pharmacologically related to αMT. Its central stimulant effects are thought not to result primarily from its activity as a monoamine oxidase inhibitor (MAOI) but from its structural resemblance to indolic psychedelics. Unlike αMT, α-ethyltryptamine is less stimulating and hallucinogenic. Its effects are often described as being more similar to entactogens like MDMA, also known as “Ecstasy.”
- What are the neurotransmitters affected by α-Ethyltryptamine?
- α-Ethyltryptamine acts as a releasing agent for serotonin, norepinephrine, and dopamine, with serotonin being the primary neurotransmitter affected. It also functions as a non-selective serotonin receptor agonist.
- Is α-Ethyltryptamine associated with any potential risks or dangers?
- Just like many other substances that release serotonin, α-Ethyltryptamine can pose risks when taken in excessive amounts or when combined with other drugs, particularly other MAOIs. These situations can lead to potential health concerns or adverse reactions.
- Is α-Ethyltryptamine legally regulated?
- In the United States, α-Ethyltryptamine is classified as a Schedule I controlled substance. Legal regulations regarding its status may vary from one country to another.
References
- Anvisa’s Regulatory Control: As of July 24, 2023, the Brazilian Health Regulatory Agency (Anvisa) has included α-Ethyltryptamine (αET) on its list of controlled substances. This regulatory action places αET under special control within the country, classifying it as a substance with specific regulatory restrictions. This move aims to manage and monitor the distribution and use of αET. Please note that the regulations and legal status of substances can change, and it’s essential to stay updated with your local authorities.
- Erowid Information: Erowid, a valuable online resource for drug-related information, provides a dedicated “α-ethyltryptamine (αET) Vault” where you can find information and community-contributed insights regarding αET. While this resource can offer valuable information, always exercise caution and critical thinking when researching or considering the use of any substances.
- Historical Clinical Development: α-Ethyltryptamine (αET) has an intriguing history. Initially, it was developed by the Upjohn chemical company in the United States during the 1960s under the name “Monase.” It was explored as a potential antidepressant, but its clinical development was discontinued due to the emergence of a medical condition known as agranulocytosis, which was deemed unacceptable.
- Structural and Pharmacological Relation: α-Ethyltryptamine (αET) is structurally and pharmacologically related to α-methyltryptamine (αMT) and other indolic psychedelics. Its central stimulant effects are thought to be associated with its structural similarities to these psychedelics. In contrast to αMT, αET is considered to be less stimulating and hallucinogenic. Instead, its effects are often described as more similar to entactogens like MDMA.
- Neurotransmitter Effects: α-Ethyltryptamine acts as a releasing agent for several neurotransmitters, including serotonin, norepinephrine, and dopamine. Among these, serotonin is the primary neurotransmitter affected. Additionally, it functions as a non-selective serotonin receptor agonist.
- Safety Considerations: As with many substances that influence serotonin, there can be risks associated with α-Ethyltryptamine. Excessive doses or combinations with other drugs, particularly other monoamine oxidase inhibitors (MAOIs), may lead to adverse reactions. It’s essential to be aware of potential health concerns when using such substances.
- Serotonin Releasers and MAOIs: Combining substances that release serotonin, like αET, with MAOIs can be problematic and even fatal. This combination can lead to serotonin toxicity, which can have severe consequences. It’s crucial to be cautious about potential interactions with other substances.