Dermorphin Chemical Properties

Melting point:

157-159 °C

Boiling point:

1323.8±65.0 °C(Predicted)

Density 

1.363±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Soluble in DMSO

pka

9.83±0.15(Predicted)

form 

powder

color 

white to off-white

Sequence

H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2

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

InChIKey

FHZPGIUBXYVUOY-VWGYHWLBSA-N

SMILES

C(N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N)(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)[C@@H](N)CC1C=CC(O)=CC=1)CC1C=CC=CC=1)CC1C=CC(O)=CC=1

Safety Information

WGK Germany 

3

Dermorphin Usage And Synthesis

Description

Dermorphin was first isolated from the skin of the skin of South American frogs of the genus Phyllomedusa.  It is a high potency natural opiate peptide that binds selectively to mu-opioid receptors.

Uses

A mu-opioid receptor agonist

Definition

ChEBI: Dermorphin is an oligopeptide.

Side effects

Like μ-opiate agonists, dermorphins produce antinociception and also catalepsy, respiratory depression, constipation, tolerance, and dependence, although at a lower degree than morphine does[1].

in vitro

Dermorphin, a peptide isolated from the skin of Phyllomedusa frogs and the peptide receptor (NOP) component by the endogenous agonist nociceptin/orphanin FQ (N/OFQ). In displacement binding studies at CHOhMu, Dermorphin and DeNo displac the binding of [3H]-DPN in a concentration dependent and saturable manner. Dermorphin displays an affinity of 7.17, while N/OFQ fails to displace [3H]-DPN at the Delta receptor. Dermorphin and DeNo stimulate the binding of GTPγ[35S] in a concentration dependent and saturable manner at the Mu receptor.

References

[1] Negri, L. P. Melchiorri and R. Lattanzi. “Opioid and Bv8 Peptides.”Handbook of Biologically Active Peptides (Second Edition) 2013:376-383.

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