Dermorphin

Source: Wikipedia, the free encyclopedia.
Dermorphin
Skeletal formula of dermorphin
Space-filling model of the dermorphin molecule
Names
Other names
Tyrosyl-alanyl-phenylalanyl-glycyl-tyrosyl-prolyl-serinamide
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-

mu opioid receptors.[2][3] Dermorphin is about 30–40 times more potent than morphine, but theoretically may be less likely to produce drug tolerance and addiction due to its high potency.[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-

posttranslational modification carried out by an amino acid isomerase.[6] This unusual process is needed because the D-alanine in this peptide is not among the 20 amino acids coded for in the genetic code and thus the peptide cannot be synthesized in the usual way from the encodings in the genome of an organism
.

Illicit use

Dermorphin has been illegally used in

performance-enhancing drug. Due to dermorphin's painkilling activity, horses treated with dermorphin may run harder than they would otherwise.[7]

See also

References

  1. PMID 8981054
    .
  2. PMID 9949868. {{cite book}}: |journal= ignored (help)CS1 maint: DOI inactive as of January 2024 (link
    )
  3. PMID 2544892
    .
  4. PMID 7195758
    .
  5. PMID 8157620
    .
  6. PMID 8633012
    .
  7. ^ Bogdanich W (19 June 2012). "Turning to Frogs for Illegal Aid in Horse Races". New York Times. Retrieved 19 June 2012.
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