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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.

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  • 42381-05-5 Structure
  • Basic information

    1. Product Name: 2-aminoadamantane-2-carboxylic acid
    2. Synonyms: 2-aminoadamantane-2-carboxylic acid;2-AMino-2-adaMantanecarboxylic acid
    3. CAS NO:42381-05-5
    4. Molecular Formula: C11H17NO2
    5. Molecular Weight: 195.26
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 42381-05-5.mol
    9. Article Data: 2
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 346.2 °C at 760 mmHg
    3. Flash Point: 163.2 °C
    4. Appearance: /
    5. Density: 1.238 g/cm3
    6. Vapor Pressure: 1.03E-05mmHg at 25°C
    7. Refractive Index: 1.57
    8. Storage Temp.: Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. PKA: 2.49±0.20(Predicted)
    11. CAS DataBase Reference: 2-aminoadamantane-2-carboxylic acid(CAS DataBase Reference)
    12. NIST Chemistry Reference: 2-aminoadamantane-2-carboxylic acid(42381-05-5)
    13. EPA Substance Registry System: 2-aminoadamantane-2-carboxylic acid(42381-05-5)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 42381-05-5(Hazardous Substances Data)

42381-05-5 Usage

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

Check Digit Verification of cas no

The CAS Registry Mumber 42381-05-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,2,3,8 and 1 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 42381-05:
(7*4)+(6*2)+(5*3)+(4*8)+(3*1)+(2*0)+(1*5)=95
95 % 10 = 5
So 42381-05-5 is a valid CAS Registry Number.
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)

42381-05-5Relevant articles and documents

The synthesis of neurotensin antagonist SR 48692 for prostate cancer research

Baxendale,Cheung,Kitching,Ley,Shearman

, p. 4378 - 4387 (2013/07/27)

An improved synthesis of the molecule SR 48692 is presented and its use as a neurotensin antagonist biological probe for use in cancer research is described. The preparation includes an number of enhanced chemical conversions and strategies to overcome some of the limiting synthetic transformations in the original chemical route.

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