≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
p-Ethynylphenylalanine (4-Ethynyl-L-phenylalanine) is a potent, selective, reversible and competitive inhibitor of tryptophan hydroxylase (TPH) , with a K i of 32.6 μM
In Vitro
p-Ethynylphenylalanine selectively and reversibly inhibits the biosynthesis of serotonin. p-Ethynylphenylalanine has a low affinity for various recombinant 5-HT receptors (5-HT 1 , 5-HT 2 , 5-HT 4 , 5-HT 5 , 5-HT 6 , and 5-HT 7 ). MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
p-Ethynylphenylalanine (30 mg/kg; i.p.) decreases in 5-HT and 5-HIAA levels in the rat midbrain but not in tissue . p-Ethynylphenylalanine does not inhibit the aromatic amino acid decarboxylase . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Male Sprague-Dawley rats (200 g) Dosage: 30 mg/kg Administration: Intraperitoneal injection Result: Decreased in 5-HT and 5-HIAA levels in the rat midbrain.
Form:Solid
IC50& Target:Ki: 32.6 μM (TPH)
| Canonical Smiles | C#CC1=CC=C(C=C1)CC(C(=O)O)N |
|---|---|
| IUPAC Name | (2S)-2-amino-3-(4-ethynylphenyl)propanoic acid |
| InChIKey | PPDNGMUGVMESGE-JTQLQIEISA-N |
| INCHI | 1S/C11H11NO2/c1-2-8-3-5-9(6-4-8)7-10(12)11(13)14/h1,3-6,10H,7,12H2,(H,13,14)/t10-/m0/s1 |
| Isomeric SMILES | C#CC1=CC=C(C=C1)C[C@@H](C(=O)O)N |
| Alternate CAS | 278605-15-5 |
| PubChem CID | 25216972 |
| MeSH Entry Terms | p-ethynylphenylalanine;pEPA cpd |
| Molecular Weight | 189.21 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
| Direct Parent | Phenylalanine and derivatives |
| Alternative Parents | Phenylpropanoic acids L-alpha-amino acids Amphetamines and derivatives Aralkylamines Amino acids Monocarboxylic acids and derivatives Carboxylic acids Acetylides Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenylalanine or derivatives - 3-phenylpropanoic-acid - Alpha-amino acid - Amphetamine or derivatives - L-alpha-amino acid - Aralkylamine - Monocyclic benzene moiety - Benzenoid - Amino acid - Acetylide - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Primary amine - Primary aliphatic amine - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic oxygen compound - Amine - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
| External Descriptors | Not available |
| Solubility | 1M NaOH : 240 mg/mL (1268.43 mM; ultrasonic and adjust pH to 11 with NaOH) 1M HCl : 240 mg/mL (1268.43 mM; ultrasonic and adjust pH to 1 with HCl) DMSO : 2.22 mg/mL (11.73 mM; Need ultrasonic) |
|---|---|
| Molecular Weight | 189.210 g/mol |
| XLogP3 | -1.300 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 4 |
| Exact Mass | 189.079 Da |
| Monoisotopic Mass | 189.079 Da |
| Topological Polar Surface Area | 63.300 Ų |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Complexity | 245.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
