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Dermorphin
Skeletal formula of dermorphin
Space-filling model of the dermorphin molecule
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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
  • 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
C40H50N8O10
Molar mass 802.886 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Dermorphin is a hepta-peptide first isolated from the skin of South American frogs belonging to the genus Phyllomedusa.[1] The peptide is an agonist with high potency and selectivity to mu opioid receptors.[2][3] Dermorphin is about 30–40 times more potent than morphine.[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 similar D-amino acid containing peptides have only been found in bacteria, amphibians, and molluscs.[5] Dermorphin appears to be made via the posttranslational modification of a precursor peptide by an amino acid isomerase.[6] This unusual process is needed because the D-alanine in this peptide is not part of the standard genetic code.

Illicit use

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

See also

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References

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  1. ^ Melchiorri P, Negri L (1996). "The dermorphin peptide family". Gen. Pharmacol. 27 (7): 1099–107. doi:10.1016/0306-3623(95)02149-3. PMID 8981054.
  2. ^ Amiche M, Delfour A, Nicolas P (1998). "Opioid peptides from frog skin". D-Amino Acids in Sequences of Secreted Peptides of Multicellular Organisms. Vol. 85. pp. 57–71. doi:10.1007/978-3-0348-8837-0_4 (inactive 11 July 2025). ISBN 978-3-0348-9794-5. PMID 9949868. {{cite book}}: |journal= ignored (help)CS1 maint: DOI inactive as of July 2025 (link)
  3. ^ Erspamer V, Melchiorri P, Falconieri-Erspamer G, et al. (1989). "Deltorphins: a family of naturally occurring peptides with high affinity and selectivity for delta opioid binding sites". Proc. Natl. Acad. Sci. U.S.A. 86 (13): 5188–92. Bibcode:1989PNAS...86.5188E. doi:10.1073/pnas.86.13.5188. PMC 297583. PMID 2544892.
  4. ^ Broccardo M, Erspamer V, Falconieri Erspamer G, et al. (1981). "Pharmacological data on dermorphins, a new class of potent opioid peptides from amphibian skin". Br. J. Pharmacol. 73 (3): 625–31. doi:10.1111/j.1476-5381.1981.tb16797.x. PMC 2071698. PMID 7195758.
  5. ^ Kreil G (15 April 1994). "Peptides containing a D-amino acid from frogs and molluscs". J. Biol. Chem. 269 (15): 10967–70. doi:10.1016/S0021-9258(19)78075-2. PMID 8157620.
  6. ^ Heck SD, Faraci WS, Kelbaugh PR, Saccomano NA, Thadeio PF, Volkmann RA (1996). "Posttranslational amino acid epimerization: enzyme-catalyzed isomerization of amino acid residues in peptide chains". Proc. Natl. Acad. Sci. U.S.A. 93 (9): 4036–9. Bibcode:1996PNAS...93.4036H. doi:10.1073/pnas.93.9.4036. PMC 39482. PMID 8633012.
  7. ^ Bogdanich W (19 June 2012). "Turning to Frogs for Illegal Aid in Horse Races". New York Times. Retrieved 19 June 2012.

📚 Artikel Terkait di Wikipedia

Kambo (drug)

effects. Peptides found in the frog secretions include the opioid peptides dermorphin and deltorphin, the vasodilator sauvagine, and dermaseptin, which exhibits

DALDA

agonist of the mu opioid receptor. It is a metabolically stable analogue of dermorphin, a naturally occurring opioid peptide secreted by some species of South

Rostral ventromedial medulla

with a dermorphin-saporin conjugate reduced the duration of allodynia and hyperalgesia caused by a nerve injury. Treatment with the dermorphin-saporin

Phyllomedusa bicolor

contains the opioid peptides deltorphin, deltorphin I, deltorphin II and dermorphin. The secretion, known as Kambo or Sapo, has seen increasing popularity

Mitragyna speciosa

Casokefamide Cebranopadol Chloroxymorphamine Codeine DADLE DAMGO (DAGO) Dermorphin Desmetramadol (desmethyltramadol) Desomorphine Deumitragynine Dextromoramide

List of psychoactive plants, fungi, and animals

opioid peptides, including deltorphin, deltorphin I, deltorphin II, and dermorphin Hallucinogenic fish Ocean life containing DMT analogs: Smenospongia aurea:

Lean (drug)

Casokefamide Cebranopadol Chloroxymorphamine Codeine DADLE DAMGO (DAGO) Dermorphin Desmetramadol (desmethyltramadol) Desomorphine Deumitragynine Dextromoramide

List of opioids

DALDA (Tyr-D-Arg-Phe-Lys-NH2)[49] Deltorphin I Deltorphin II Deprolorphin Dermorphin DPDPE  Frakefamide Gliadorphin Gluten exorphins Hemorphin-4 Metkefamide