144035-23-4

Basic information

• Product Name: 5-(1H-1,2,4-Triazol-1-ylmethyl)-1H-indole-3-ethanamine
• Synonyms: 5-(1H-1,2,4-Triazol-1-ylmethyl)-1H-indole-3-ethanamine;2-(6-((1H-1,2,4-Triazol-1-yl)methyl)-1H-indol-3-yl)ethanamine;N10-DidesMethyl Rizatriptan
• CAS NO: 144035-23-4
• Molecular Formula: C₁₃H₁₅N₅
• Molecular Weight: 241.29
• EINECS: 604-604-1
• Mol File: 144035-23-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 528.8±60.0 °C(Predicted)
• Appearance: /
• Density: 1.35
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform, Methanol
• PKA: 16.95±0.30(Predicted)
• CAS DataBase Reference: 5-(1H-1,2,4-Triazol-1-ylmethyl)-1H-indole-3-ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(1H-1,2,4-Triazol-1-ylmethyl)-1H-indole-3-ethanamine(144035-23-4)
• EPA Substance Registry System: 5-(1H-1,2,4-Triazol-1-ylmethyl)-1H-indole-3-ethanamine(144035-23-4)

Safety Data

• Hazardous Substances Data: 144035-23-4(Hazardous Substances Data)

Usage

Description

5-(1H-1,2,4-Triazol-1-ylmethyl)-1H-indole-3-ethanamine is an organic compound with a unique chemical structure that features a triazole and indole ring system. It is known for its potential applications in various fields due to its chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
5-(1H-1,2,4-Triazol-1-ylmethyl)-1H-indole-3-ethanamine is used as an intermediate in the synthesis of various pharmaceutical compounds for the treatment of different medical conditions. Its unique structure allows for the development of new drugs with improved efficacy and reduced side effects.
Used in Chemical Research:
In the field of chemical research, 5-(1H-1,2,4-Triazol-1-ylmethyl)-1H-indole-3-ethanamine serves as a valuable compound for studying the properties and reactivity of triazole and indole ring systems. This can lead to the discovery of new chemical reactions and the development of novel synthetic methods.
Used in Material Science:
The compound may also find applications in material science, where its unique structure could be utilized in the design and synthesis of new materials with specific properties, such as improved conductivity, stability, or optical characteristics.
Used in the Synthesis of Rizatriptan (R545000) Related Compounds:
5-(1H-1,2,4-Triazol-1-ylmethyl)-1H-indole-3-ethanamine is used as an intermediate in the synthesis of N10-Didesmethyl Rizatriptan, which is related to Rizatriptan (R545000). Rizatriptan is a medication used to treat migraine headaches, and the synthesis of related compounds can potentially lead to the development of new treatments for migraines and other conditions.

Upstream product

• 29882-07-3 4-chlorobutanal dimethyl acetal 
• 144035-22-3 4-(1,2,4-triazol-1-ylmethyl)phenylhydrazine 
• 6346-09-4 4-aminobutyrylaldehyde diethylacetal 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 144235-64-3 4-(1,2,4-triazolylmethyl)phenylamine hydrochloride 
• 119192-09-5 1-(4-nitrophenyl)methyl-1,2,4-triazole 
• 154748-67-1 1-(4-hydrazinophenyl)-methyl-1,2,4-triazole dihydrochloride 

Downstream Products

• 144034-80-0 rizatriptan 
• 144035-40-5 N-Benzyl-2[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine 

Relevant articles and documents

N-Desmethyltriptans: One pot efficient synthesis of N-methyl-2-5- [substituted- 1H- indole-3-yl]ethanamines

A straightforward and highly improved method to synthesize N-methyl-2-[5-[substituted-lH-indole-3-yl]ethanamines 4-6, which are the metabolites of tryptans 1-3, is reported. The significance of the process is its simplicity and efficiency in isolating the N- desmethyltriptans derivatives as a free base.

Synthesis and serotonergic activity of N,N-dimethyl-2-[5-(1,2,4-triazol- 1-ylmethyl)-1H-indol-3-yl]ethylamine and analogues: Potent agonists for 5- HT(1D) receptors

The synthesis and the 5-HT receptor activity of a novel series of N,N- dimethyltryptamines substituted in the 5-position with an imidazole, triazole, or tetrazole ring are described. The objective of this work was to identify potent and selective 5-HT(1D) receptor agonists with high oral bioavailability and low central nervous system penetration. Compounds have been prepared in which the azole ring is attached through either nitrogen or carbon to the indole. Conjugated and methylene-bridged derivatives have been studied (n = 0 or 1). Substitution of the azole ring has been explored either α or β to the point of attachment to indole. In a series of N-linked azoles (X = N), simple unsubstituted compounds have high affinity and selectivity for 5-HT(1D) receptors. It is proposed that for good affinity and selectivity a hydrogen bond acceptor interaction with the 5-HT(1D) receptor, through a β-nitrogen in the azole ring, is required. In a series of C-linked triazoles and tetrazoles (X = C), optimal affinity and selectivity for the 5-HT(1D) receptor was observed when the azole ring is substituted at the 1-position with a methyl or ethyl group. This study has led to the discovery of the 1,2,4-triazole 10a (MK-462) as a potent and selective 5-HT(1D) receptor agonist which has high oral bioavailability and rapid oral absorption. The in vitro activity and the preliminary pharmacokinetics of compounds in this series are presented.