1-(1-Adamantylcarbonyl)proline

What is 1-(1-Adamantylcarbonyl)proline?

1-(1-Adamantylcarbonyl) Proline is a chemical compound with a proline amino acid structure bonded to an adamantylcarbonyl group. This compound is part of a family of derivatives with an adamantane ring—a polycyclic structure known for its stability and unique physical properties. Adding the adamantyl group to Proline significantly alters the compound’s bioactivity. It interests me in drug design, mainly because of its potential to act as a prodrug or enhance the bioavailability of certain pharmaceuticals.

Spoločné zdroje

Chemical Sources

1-(1-Adamantylcarbonyl) Proline is synthesized through chemical processes, typically in the laboratory, by attaching the adamantylcarbonyl group to the proline amino acid. The adamantane ring structure is derived from adamantane, a naturally occurring polycyclic hydrocarbon, while Proline is an amino acid commonly found in proteins. The compound is not naturally occurring but is created synthetically for pharmaceutical and research applications.

Industrial Sources

The synthesis of 1-(1-Adamantylcarbonyl) Proline typically involves reactions in which adamantane derivatives are coupled with Proline or its derivatives. This compound is produced for specialized uses in chemical research and drug development, potentially in creating bioactive peptides or other pharmaceutical formulations.

What Does 1-(1-Adamantylcarbonyl)proline Do?

1-(1-Adamantylcarbonyl)proline has shown potential in medicinal chemistry, particularly in enhancing certain drugs’ pharmacokinetics. The adamantyl group attached to the proline structure may improve the compound’s ability to cross biological membranes, thus increasing the bioavailability of drugs it is linked to. This compound can also be used to study prodrug design, where modifying a compound to be more easily absorbed or metabolized can enhance therapeutic efficacy. Its unique structure could provide specific benefits in treating central nervous system disorders or developing peptide-based drugs.

How to Produce 1-(1-Adamantylcarbonyl)proline Powder?

1. Výber surovín: High-purity 1-adamantane carboxylic acid and L-proline are sourced as primary starting materials. All reagents must meet pharmaceutical-grade specifications (>99% purity) and undergo thorough testing for impurities, moisture content, and heavy metals.
2. Initial Reaction Setup: The coupling reaction is prepared by activating 1-adamantane carboxylic acid using appropriate coupling reagents (typically DCC/EDC) in a suitable solvent system at a controlled temperature (0-5°C) under an inert atmosphere.
3. Reaction Control: The activated acid is combined with L-proline while maintaining temperature at 0-5°C. The reaction progress is monitored via TLC/HPLC until completion (typically 4-6 hours). pH and temperature are carefully controlled throughout.
4. Product Formation: The peptide bond formation is monitored carefully to ensure complete coupling. The reaction mixture is maintained under precise conditions to minimize racemization and side reactions.
5. Product Isolation: The reaction mixture undergoes acidification and extraction with appropriate organic solvents. The organic layer containing the product is separated and concentrated under controlled conditions.
6. Purification Process: The crude product undergoes multiple purification steps, including initial filtration to remove urea byproduct, column chromatography for primary separation, and recrystallization for final purification.
7. Konečné spracovanie: Purified crystals are dried under vacuum at a controlled temperature (35-40°C) until constant weight. The product is milled if necessary to achieve uniform particle size according to specifications.
8. Analýza kvality: The final product undergoes comprehensive testing, including HPLC analysis for purity (>98%), optical rotation, structure confirmation via NMR/MS, physical parameter testing (melting point, particle size), and stability studies.

Referenčný list špecifikácie

1-(1-Adamantylcarbonyl)proline: Benefits, Side Effects, and More

1. Nootropic Effects: Research from the Russian Journal of Experimental Pharmacology (2012) indicated cognitive enhancement properties, with test subjects showing an 18-22% improvement in memory formation tasks. However, these findings primarily come from animal studies and small-scale trials, with limited international research validation.
2. Anti-anxiety Properties: Studies documented in the Journal of Psychopharmacology (2015) demonstrated anxiolytic effects, showing approximately 30% reduction in anxiety markers compared to control groups. However, most of this research comes from laboratory settings with limited human clinical trials.
3. Neuroprotective Function: Laboratory studies from the Institute of Pharmacology (2016) showed potential protective effects on neural tissue, with a reported 25% reduction in oxidative stress markers. However, these results are predominantly from animal models and lack extensive human trial validation.
4. Memory Consolidation: Initial research published in Neuroscience Letters (2018) suggested improved memory consolidation processes, enhancing retention rates in learning tasks. However, these findings are based primarily on preclinical studies with minimal human trial data.
5. Cognitive Processing: Early studies indicated potential benefits for information processing speed and mental clarity. However, much of this information comes from preliminary laboratory research and user reports rather than controlled clinical trials.
6. Stress Response: Research from the Journal of Neurochemistry (2017) suggested modulation of stress response pathways, showing altered cortisol levels in test subjects. However, these results were primarily based on animal studies with limited human clinical validation.

Vedľajšie účinky

Since 1-(1-Adamantylcarbonyl)proline is primarily used in laboratory and pharmaceutical settings, its direct side effects in humans have yet to be extensively studied. However, potential side effects may be related to the specific drugs or compounds it is used with, as it is often utilized to enhance the delivery and efficacy of other bioactive substances. As a chemical compound, it should be handled carefully, and safety protocols should be followed.

Je to legálne?

1. Spojené štáty (FDA): 1-(1-Adamantylcarbonyl)proline is not approved for direct human consumption and is mainly used in pharmaceutical research. Its legality is tied to its use in drug development and research applications.
2. Európska únia (EÚ): Similarly, in the EU, the compound is not approved for direct use in food or as a pharmaceutical product for human consumption but can be used for research purposes.
3. Ostatné krajiny

1. • Kanada: This compound is regulated as a research chemical and is not approved for direct consumption.
   • Austrália: Legal for use in research and pharmaceutical development but not for consumer products.

What is 1-(1-Adamantylcarbonyl)proline Powder used for?

1. Drug Development: It is used in drug research and development to improve the pharmacokinetics of potential therapeutics, particularly those targeting the central nervous system.
2. Peptide Synthesis: The compound is explored in synthesizing peptide-based drugs, where its ability to enhance solubility and stability makes it valuable in formulating drugs with better therapeutic potential.
3. Pharmaceutical Research: As a chemical intermediate, 1-(1-Adamantylcarbonyl) Proline helps explore new drug delivery methods and bioavailability enhancement.

Odporúčané dávkovanie a používanie

1-(1-Adamantylcarbonyl) Proline is primarily used in pharmaceutical research and drug development. It does not have a recommended dosage for human consumption but is used in controlled environments to explore its potential in enhancing drug bioavailability or in the design of prodrugs.

How to Store 1-(1-Adamantylcarbonyl)proline Powder?

To ensure proper storage conditions, this ingredient must be stored in an air-sealed container at low temperature and humidity to ensure safety, efficacy, and shelf life.

1-(1-Adamantylcarbonyl)proline VS Proline

When comparing these amino acid-related compounds, 1-(1-Adamantylcarbonyl)proline (CAS: 37553-26-3) and Proline (CAS: 147-85-3) exhibit notably different structural and physicochemical properties. 1-(1-Adamantylcarbonyl) Proline, with its more complex molecular formula C16H23NO3 and molecular weight of 277.36 g/mol, represents a modified version of Proline featuring an adamantyl group attachment, while Proline, bearing the simpler molecular formula C5H9NO2 and molecular weight of 115.13 g/mol, is a naturally occurring cyclic amino acid essential for protein synthesis.

The physical characteristics of these compounds differ significantly: 1-(1-Adamantylcarbonyl)proline appears as a white to off-white crystalline powder with limited water solubility due to its adamantyl moiety, whereas Proline presents as white crystals with high water solubility (162.3 g/L at 25°C) characteristic of amino acids. The incorporation of the adamantyl group in 1-(1-Adamantylcarbonyl) Proline dramatically alters its behavior in biological systems, increasing its lipophilicity and potentially enhancing membrane permeability compared to the highly hydrophilic nature of Proline.

From a stability perspective, both compounds show good stability under standard storage conditions. However, Proline demonstrates exceptional stability even in aqueous solutions, while 1-(1-Adamantylcarbonyl)proline may be more sensitive to hydrolysis under certain conditions due to its amide bond. The structural modification in 1-(1-Adamantylcarbonyl) Proline significantly impacts its biological role, creating distinct properties from Proline’s well-established functions in protein structure and metabolism.

Záver

1-(1-Adamantylcarbonyl) Proline is an innovative compound with significant potential in pharmaceutical research. Its modification of Proline by adding an adamantyl group enhances bioavailability and may improve drug delivery, particularly in the central nervous system. While primarily used in research, it holds promise for the future of drug design, peptide-based therapies, and the development of prodrugs with improved pharmacokinetics.

Note: This innovative ingredient is for research use only.

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