1,3-Benzodioxole-5-ethanamine
[CAS# 1484-85-1]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: 1,3-Benzodioxole-5-ethanamine
• Synonyms: 5-(2-Aminoethyl)benzodioxole; Homopiperonylamine; [2-(Benzodioxol-5-yl)ethyl]amine
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• CAS Registry Number: 1484-85-1
• EC Number: 216-060-8
• SMILES: C1OC2=C(O1)C=C(C=C2)CCN

Properties

• Solubility: Slightly soluble (2.3 g/L) (25 ºC), Calc.^*
• Density: 1.204±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 207-210 ºC^**
• Boiling point: 230 ºC (50 Torr)^***
• Flash point: 129.8±26.0 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2019 ACD/Labs)

^** Kondo, Heisaburo; Ann. Rept. ITSUU Lab. 1953, VNo. 4, P20-9.

^*** Malan, Jacques; Journal of the Chemical Society 1927, P2653-7.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H314-H315-H318-H319-H335
• Precautionary Statements: P260-P261-P264-P264+P265-P271-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P319-P321-P332+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314

Discovory and Applicatios

1,3-Benzodioxole-5-ethanamine, also known as 5-ethoxy-1,3-benzodioxole, is a chemical compound belonging to the class of substituted phenethylamines. It features a benzodioxole ring structure with an ethylamine group attached at the 5-position of the ring. This molecule is structurally related to a variety of psychoactive substances, with its core structure being similar to that of other substituted phenethylamines, such as mescaline, which is known for its hallucinogenic effects. The compound is primarily studied in the context of its chemical properties, potential pharmacological activities, and its role in the synthesis of novel compounds for use in medicinal chemistry.

The discovery of 1,3-benzodioxole-5-ethanamine can be traced back to research into the structure-activity relationships of psychoactive compounds. In the mid-20th century, scientists began exploring how different substitutions on the benzodioxole ring influenced the biological activity of related substances. The 5-position substitution, particularly the introduction of an ethylamine group, was identified as one that might enhance certain pharmacological properties while maintaining a degree of selectivity for certain receptor sites. This led to the development of 1,3-benzodioxole-5-ethanamine as a compound of interest in both synthetic chemistry and pharmacology.

Synthetically, 1,3-benzodioxole-5-ethanamine can be produced through several synthetic routes. One common method involves the alkylation of 1,3-benzodioxole with an ethylating agent, followed by the addition of an amine to form the ethylamine group. The synthesis of such compounds typically requires careful control of reaction conditions to avoid unwanted side reactions and ensure high yields of the desired product. Additionally, the presence of the benzodioxole ring can make the compound susceptible to certain oxidation or reduction processes, which can be exploited in further modifications of the molecule to create derivatives with varied biological properties.

1,3-Benzodioxole-5-ethanamine has potential applications in medicinal chemistry, particularly in the exploration of new psychoactive substances. Due to its structural similarity to known psychoactive compounds, it is studied for its possible effects on serotonin and other neurotransmitter systems in the brain. However, its precise pharmacological profile remains the subject of ongoing research. The compound may also serve as a precursor in the synthesis of other compounds that could have applications in drug discovery, particularly for conditions related to mood disorders, anxiety, or neurodegenerative diseases. Additionally, 1,3-benzodioxole-5-ethanamine may find use in the development of novel therapeutic agents through its incorporation into more complex molecular structures.

In conclusion, 1,3-benzodioxole-5-ethanamine is a promising compound with potential applications in both research and drug development. Its unique chemical structure and potential for modification make it a valuable target for synthetic chemists and pharmacologists alike. Further studies into its biological activities will determine whether it can be developed into a therapeutic agent for clinical use.

References

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2012. Application of chlorotrimethylsilane in Pictet-Spengler reaction. Monatshefte für Chemie - Chemical Monthly, 143(11).
DOI: 10.1007/s00706-012-0804-7