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N-(Phenylacetyl)-L-phenylalanine, also known as N-phenylacetyl-L-phenylalanine or NPP, is a chemical compound that belongs to the class of opioid analgesics. It is a potent and selective agonist for the μ-opioid receptor, which is the primary target for most clinically-relevant opioid analgesics. NPP has demonstrated potential in pain management and has shown promising results in preclinical trials. However, due to its structural similarity to other opioids such as fentanyl and sufentanil, NPP may also have potential for abuse and dependence. Ongoing research is being conducted to better understand its therapeutic potential and potential risks if utilized as a pharmaceutical drug.

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  • 738-75-0 Structure
  • Basic information

    1. Product Name: N-(PHENYLACETYL)-L-PHENYLALANINE
    2. Synonyms: (2S)-3-phenyl-2-[(2-phenylacetyl)amino]propanoic acid;(2S)-3-phenyl-2-[(2-phenylacetyl)amino]propionic acid;Phenylacetyl-L-Phenhylalanine;N-ALPHA-PHENYLACETYL-L-PHENYLALANINE;N-(PHENYLACETYL)-L-PHENYLALANINE;PHENYLAC-PHE-OH;PHENYLACETYL-L-PHENYLALANINE;n-(phenylacetyl)-l-phenylalaninemw283.3
    3. CAS NO:738-75-0
    4. Molecular Formula: C17H17NO3
    5. Molecular Weight: 283.32
    6. EINECS: 604-604-1
    7. Product Categories: Amino Acids;I - Z;Modified Amino Acids
    8. Mol File: 738-75-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 547.4 °C at 760 mmHg
    3. Flash Point: 284.8 °C
    4. Appearance: /
    5. Density: 1.213 g/cm3
    6. Vapor Pressure: 8.16E-13mmHg at 25°C
    7. Refractive Index: 1.595
    8. Storage Temp.: −20°C
    9. Solubility: N/A
    10. PKA: 3.60±0.10(Predicted)
    11. CAS DataBase Reference: N-(PHENYLACETYL)-L-PHENYLALANINE(CAS DataBase Reference)
    12. NIST Chemistry Reference: N-(PHENYLACETYL)-L-PHENYLALANINE(738-75-0)
    13. EPA Substance Registry System: N-(PHENYLACETYL)-L-PHENYLALANINE(738-75-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 738-75-0(Hazardous Substances Data)

738-75-0 Usage

Uses

Used in Pharmaceutical Industry:
N-(Phenylacetyl)-L-phenylalanine is used as an opioid analgesic for pain management due to its potent and selective agonist activity on the μ-opioid receptor. It has shown promising results in preclinical trials, making it a potential candidate for the development of new pain management therapies.
Used in Research and Development:
NPP is used in ongoing research to better understand its therapeutic potential and potential risks if utilized as a pharmaceutical drug. This includes studying its structural similarity to other opioids and its potential for abuse and dependence, as well as exploring novel drug delivery systems to enhance its efficacy and safety profile in pain management applications.

Check Digit Verification of cas no

The CAS Registry Mumber 738-75-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,3 and 8 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 738-75:
(5*7)+(4*3)+(3*8)+(2*7)+(1*5)=90
90 % 10 = 0
So 738-75-0 is a valid CAS Registry Number.
InChI:InChI=1/C17H17NO3/c19-16(12-14-9-5-2-6-10-14)18-15(17(20)21)11-13-7-3-1-4-8-13/h1-10,15H,11-12H2,(H,18,19)(H,20,21)/t15-/m0/s1

738-75-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-3-phenyl-2-[(2-phenylacetyl)amino]propanoic acid

1.2 Other means of identification

Product number -
Other names N-phenylacetyl-L-phenylalanine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:738-75-0 SDS

738-75-0Relevant articles and documents

GRANZYME B DIRECTED IMAGING AND THERAPY

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Page/Page column 82; 97, (2019/09/04)

Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.

A one-pot amidation of primary nitroalkanes

Schwieter, Kenneth E.,Johnston, Jeffrey N.

supporting information, p. 152 - 155 (2015/12/26)

It has been over a half-century since Kornblum demonstrated the conversion of a primary nitroalkane to a carboxylic acid; addition of an amine results in carboxylic acid formation as well. We describe the formation of amides from terminal nitroalkanes in a two-step, one-pot reaction involving tandem halogenation/umpolung amide synthesis (UmAS).

Intramolecular interactions of a phenyl/perfluorophenyl pair in the formation of supramolecular nanofibers and hydrogels

Hsu, Shu-Min,Lin, Yu-Chun,Chang, Jui-Wen,Liu, Yu-Hao,Lin, Hsin-Chieh

supporting information, p. 1921 - 1927 (2014/03/21)

A new system for the incorporation of a phenyl/perfluorophenyl pair in the structure of a peptide hydrogelator was developed. The strategy is based on the idea that the integration of an end-capped perfluorophenyl group and a phenylalanine with a phenyl moiety in the side chain forms an intramolecular phenyl/perfluorophenyl pair, which can be used to promote the formation of the supramolecular nanofibers and hydrogels. This work illustrates the importance of structure-hydrogelation relationship and provides new insights into the design of self-assembly nanobiomaterials. Intramolecular binding: The incorporation of a phenyl/perfluorophenyl pair into the structure of a peptide hydrogelator leads to the formation of the supramolecular nanofibers. The quadrupole-dipole- quadrupole (q-d-q) interactions between the aromatic rings facilitate self-assembly. This work illustrates the importance of the structure- hydrogelation relationship and provides new insights into the design of self-assembled nanobiomaterials. Copyright

Thermodynamics of phenylacetamides synthesis: Linear free energy relationship with the pK of amine

Guranda, Dorel T.,Ushakov, Gennadij A.,Yolkin, Petr G.,Svedas, Vytas K.

, p. 48 - 53 (2012/05/19)

The effective equilibrium constants K′C expressed through the total concentrations of the reagents for the synthesis of N-phenylacetyl-derivatives in aqueous medium from phenylacetic acid and various primary amino compounds have been determined with penicillin acylase as a catalyst. Broad specificity of penicillin acylase (EC 3.5.1.11) to amino components made possible to investigate the acylation of primary amines with different structures and physicochemical properties. Analysis of different components of the effective standard Gibbs energy change ΔGC o′ has revealed favorable thermodynamics for the synthesis of phenylacetamides from unionized substrates forms, however the ionization of reactants carboxy and amino groups in aqueous solutions pushes the equilibrium position to the hydrolysis especially in case of highly basic amines. A linear correlation between the standard Gibbs energy change for amide bond formation from the unionized reagents species and the basicity of amino group was observed: ΔGTo=-3.56pKamine+7.71(kJ/mol). The established linear free energy relationship (LFER) allows to predict the thermodynamic parameters for direct condensation of phenylacetic acid with any amine of known pK. Condensation of phenylacetic acid and amines with pK value within 1.5-8.5 was shown to be thermodynamically favorable in homogeneous aqueous solution. .

Alcaligenes faecalis penicillin G acylase-catalyzed enantioselective acylation of dl-phenylalanine and derivatives in aqueous medium

Gong, Xiangyu,Su, Erzheng,Wang, Pixiang,Wei, Dongzhi

supporting information; experimental part, p. 5398 - 5402 (2011/10/19)

A new strategy based on enantioselective acylation properties of relatively unknown penicillin G acylase from Alcaligenes faecalis has been developed for the production of pharmacologically interesting enantiomerically pure d-phenylalanine. In order to get high reaction rate and enantioselectivity, two key factors (pH and temperature) and eight different acyl donors were optimized, and the optimal acylation reaction was carried out at pH 10, 35 °C, using phenylacetamide as the acyl donor. This enantioselective acylating method is also illustrated by the effective production of five different p-substituted phenylalanine derivatives in enantiopure.

An improved method of amide synthesis using acyl chlorides

Zhang, Li,Wang, Xiao-jun,Wang, Jing,Grinberg, Nelu,Krishnamurthy, DhileepKumar,Senanayake, Chris H.

supporting information; experimental part, p. 2964 - 2966 (2009/08/07)

A simple, mild and highly efficient condition for amide synthesis from acyl chlorides has been developed to minimize hydrolysis, racemization and other side reactions. This method should expand capabilities in the peptide coupling area.

Selektive Umfunktionalisierung der terminalen Amidgruppe offenkettiger Polyamide via 2-Oxazolin-5-one als Zwischenstufen

Obrecht, Daniel,Heimgartner, Heinz

, p. 482 - 487 (2007/10/02)

Treatment of aqueous or alcoholic solutions of diamides of type 2 with HCl leads to the formation of amide-acids and amide-esters of type 3 (Scheme 1 and Table).It has been shown, that 2-oxazolin-5-ones of type 4 are intermediates of this selective transf

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