Dermorphin is a natural heptapeptide and a potent µ-opioid receptor (MOR) agonist, first isolated from the skin of South American frogs belonging to the genus *Phyllomedusa*.
It exhibits high selectivity and potency for mu-opioid receptors, making it approximately 30–40 times more potent than morphine. Dermorphin’s amino acid sequence is H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2.
Unlike typical peptides, it contains a D-alanine residue, which is not encoded by the genetic code and is synthesized through an unusual post-translational modification process involving an amino acid isomerase. T
his peptide is not found in humans or other mammals and has been primarily identified in bacteria, amphibians, and mollusks. Dermorphin has been illicitly used in horse racing as a performance-enhancing drug due to its potent painkilling effects.
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| Other Names | H-Tyr-D-ala-phe-gly-tyr-pro-ser-NH2, (2S)-N-[(2S)-1-amino-3-hydroxy-1-oxopropan-2-yl]-1-[(2S)-2-[[2-[[(2S)-2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]acetyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carboxamide, Tyrosyl-alanyl-phenylalanyl-glycyl-tyrosyl-prolyl-serinamide |
|---|---|
| IUPAC Name | (2S)-N-[(2S)-1-amino-3-hydroxy-1-oxopropan-2-yl]-1-[(2S)-2-[[2-[[(2S)-2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]acetyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carboxamide |
| CAS | 77614-16-5 |
| Molecular Weight | 802.9 |
| Molecular Formula | C40H50N8O10 |
| SMILES | C[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CO)C(=O)N)NC(=O)[C@H](CC4=CC=C(C=C4)O)N |