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Dermorphin

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Opioid agonist peptide compound

Dermorphin
Names


Other names Tyrosyl-alanyl-phenylalanyl-glycyl-tyrosyl-prolyl-serinamide
Identifiers
CAS Number	77614-16-5^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL278789^N
ChemSpider	4588650^N
PubChem CID	5485199
UNII	2SEC01B703^Y
CompTox Dashboard(EPA)	DTXSID40228281
InChI InChI=1S/C40H50N8O10/c1-23(44-37(55)29(41)18-25-9-13-27(50)14-10-25)36(54)46-30(19-24-6-3-2-4-7-24)38(56)43-21-34(52)45-31(20-26-11-15-28(51)16-12-26)40(58)48-17-5-8-33(48)39(57)47-32(22-49)35(42)53/h2-4,6-7,9-16,23,29-33,49-51H,5,8,17-22,41H2,1H3,(H2,42,53)(H,43,56)(H,44,55)(H,45,52)(H,46,54)(H,47,57)/t23-,29+,30+,31+,32+,33+/m1/s1^N Key: FHZPGIUBXYVUOY-VWGYHWLBSA-N^N InChI=1/C40H50N8O10/c1-23(44-37(55)29(41)18-25-9-13-27(50)14-10-25)36(54)46-30(19-24-6-3-2-4-7-24)38(56)43-21-34(52)45-31(20-26-11-15-28(51)16-12-26)40(58)48-17-5-8-33(48)39(57)47-32(22-49)35(42)53/h2-4,6-7,9-16,23,29-33,49-51H,5,8,17-22,41H2,1H3,(H2,42,53)(H,43,56)(H,44,55)(H,45,52)(H,46,54)(H,47,57)/t23-,29+,30+,31+,32+,33+/m1/s1 Key: FHZPGIUBXYVUOY-VWGYHWLBBR
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
Properties
Chemical formula	C₄₀H₅₀N₈O₁₀
Molar mass	802.886 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Dermorphin is a hepta-peptide first isolated from the skin of South Americanfrogs belonging to the genusPhyllomedusa.^[1] The peptide is a naturalopioid that binds as anagonist with high potency and selectivity tomu opioid receptors.^[2]^[3] Dermorphin is about 30–40 times more potent thanmorphine.^[4] The amino acid sequence of dermorphin is H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH₂.

Dermorphin is not found in humans or other mammals and similarD-amino acid peptides have only been found inbacteria,amphibians, andmolluscs.^[5] Dermorphin appears to be made in these through an unusualposttranslational modification carried out by an amino acidisomerase.^[6] This unusual process is needed because theD-alanine in this peptide is not among the 20 amino acids coded for in thegenetic code and thus the peptide cannot besynthesized in the usual way from the encodings in thegenome of anorganism.

Illicit use

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Dermorphin has been illegally used inhorse racing as aperformance-enhancing drug. Due to dermorphin's painkilling activity, horses treated with dermorphin may run harder than they would otherwise.^[7]