42381-05-5

Basic information

• Product Name: 2-aminoadamantane-2-carboxylic acid
• Synonyms: 2-aminoadamantane-2-carboxylic acid;2-AMino-2-adaMantanecarboxylic acid
• CAS NO: 42381-05-5
• Molecular Formula: C₁₁H₁₇NO₂
• Molecular Weight: 195.26
• Mol File: 42381-05-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 346.2 °C at 760 mmHg
• Flash Point: 163.2 °C
• Appearance: /
• Density: 1.238 g/cm³
• Vapor Pressure: 1.03E-05mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.49±0.20(Predicted)
• CAS DataBase Reference: 2-aminoadamantane-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-aminoadamantane-2-carboxylic acid(42381-05-5)
• EPA Substance Registry System: 2-aminoadamantane-2-carboxylic acid(42381-05-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 42381-05-5(Hazardous Substances Data)

Usage

Description

2-Aminoadamantane-2-carboxylic acid, also known as adamantanamine-2-carboxylic acid, is an organic compound with a unique adamantane framework. It features a nitrogen atom attached to the second carbon of the adamantane structure and a carboxylic acid group at the same position. This molecule is known for its potential applications in various fields due to its structural properties and interactions with biological systems.

Uses

Used in Pharmaceutical Industry:
2-Aminoadamantane-2-carboxylic acid is used as a γ-turn inducer for peptides, which can be crucial in the development of peptide-based drugs. Its ability to induce a specific secondary structure in peptides can enhance their stability and bioactivity, making it a valuable component in the design of novel therapeutic agents.
Used in Receptor Binding:
2-Aminoadamantane-2-carboxylic acid serves as a potential cholecystokinin-B (CCK-B) receptor selective ligand. This application is significant in the development of drugs targeting the CCK-B receptor, which is involved in various physiological processes, including appetite regulation, pain transmission, and cognitive functions.
Used in Cellular Transport Inhibition:
2-aminoadamantane-2-carboxylic acid is also known to inhibit the transport of L-leucine and L-methionine into Ehrlich ascites cells. This property can be exploited in the study of cellular transport mechanisms and the development of drugs targeting specific transport pathways, which may have implications in cancer therapy and other diseases related to cellular transport dysfunction.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 16, p. 823, 1973 DOI: 10.1021/jm00265a016

InChI:InChI=1/C11H17NO2/c12-11(10(13)14)8-2-6-1-7(4-8)5-9(11)3-6/h6-9H,1-5,12H2,(H,13,14)

Upstream product

• 50346-47-9 spiro[adamantane-2,4'-imidazolidine]-2',5'-dione 
• 700-58-3 2-Adamantanone 

Downstream Products

• 198492-70-5 2-methyl-4-(adamantane-2'-spiro)-oxazolin-5-one 
• 895167-23-4 2-{2-[2-(2-{2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyrylamino}-adamantane-2-carboxylic acid 
• 895167-06-3 2-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-adamantane-2-carboxylic acid 
• 32337-65-8 N-(2-adamantyl)phthalimide 
• 1612148-60-3 2-({[5-(2,6-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]carbonyl}amino)tricycle-[3.3.1.13,7]decane-2-carboxylic acid 
• 1613265-65-8 2-{[1-{4-[(3-DOTA(tBu)₃-aminopropyl)-(3-dimethylaminopropyl)carbamoyl]-2-isopropylphenyl}-5(2,6-dimethoxyphenyl)-1H-pyrazole-3-carbonyl]amino}adamantane-2-carboxylic acid 
• 1613265-61-4 2-{[1-{4-[(3-{[3-(DOTA(tBu)₃-methylamino)propyl]methylamino}propyl)methylcarbamoyl]-2-isopropylphenyl}-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carbonyl]amino}adamantane-2-carboxylic acid 
• 502937-07-7 2-amino-adamantane-2-carboxylic acid tert-butyl ester 
• 146362-70-1 merclinertant 
• 1443991-23-8 tert-butyl 2-[1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxamido]adamantane-2-carboxylate 
• 221051-06-5 2-acetamido-2-tricyclo[3.3.1.1.(3,7)]decanecarboxylic acid 
• 1022149-34-3 N,N-dimethyl-2-aminoadamantyl-2-carboxylic acid methyl ester 
• 1022149-33-2 N-methyl-2-aminoadamantyl-2-carboxylic acid methyl ester 
• 144876-68-6 2-aminoadamantyl-2-carboxylic acid methyl ester 

Relevant articles and documents

2-Aminoadamantane-2-carboxylic acid, a rigid, achiral, tricyclic alpha-amino acid with transport inhibitory properties.

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