DADLE

DADLE ([D-Ala2, D-Leu5]-Enkephalin) is a synthetic opioid peptide with analgesic properties. Although it is often considered a selective delta opioid receptor agonist, it also binds to the μ1 subtype of mu opioid receptors.

DADLE
Names
IUPAC name
(2R)-2-[[(2S)-2-[[2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
Other names
• [D-Ala2, D-Leu5]-Enkephalin
• L-Tyrosyl-D-alanylglycyl-L-phenylalanyl-D-Leucine
• N-(N-(N-(N-L-tyrosyl-D-alanyl)glycyl)-L-phenylalanyl)-D-Leucine
• Tyr-D-Ala-Gly-Phe-D-Leu-OH
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.059.337
PubChem CID
UNII
InChI
  • InChI=1S/C29H39N5O7/c1-17(2)13-24(29(40)41)34-28(39)23(15-19-7-5-4-6-8-19)33-25(36)16-31-26(37)18(3)32-27(38)22(30)14-20-9-11-21(35)12-10-20/h4-12,17-18,22-24,35H,13-16,30H2,1-3H3,(H,31,37)(H,32,38)(H,33,36)(H,34,39)(H,40,41)/t18-,22+,23+,24-/m1/s1 N
    Key: ZHUJMSMQIPIPTF-IBURTVSXSA-N N
  • InChI=1/C29H39N5O7/c1-17(2)13-24(29(40)41)34-28(39)23(15-19-7-5-4-6-8-19)33-25(36)16-31-26(37)18(3)32-27(38)22(30)14-20-9-11-21(35)12-10-20/h4-12,17-18,22-24,35H,13-16,30H2,1-3H3,(H,31,37)(H,32,38)(H,33,36)(H,34,39)(H,40,41)/t18-,22+,23+,24-/m1/s1
    Key: ZHUJMSMQIPIPTF-IBURTVSXBS
SMILES
  • N[C@H](C(N[C@H](C)C(NCC(N[C@@H](CC1=CC=CC=C1)C(N[C@H](CC(C)C)C(O)=O)=O)=O)=O)=O)CC2=CC=C(O)C=C2
Properties
Chemical formula
 C29H39N5O7
Molar mass 569.659 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 YN ?)
Infobox references

Treatment with DADLE results in transient depression of mean arterial blood pressure and heart rate.[1][2]

Its peptide sequence is Tyr-D-Ala-Gly-Phe-D-Leu.

See also

References
  1. "Medical Dictionary Online". Archived from the original on 2007-08-28. Retrieved 2007-11-10.
  2. Online Medical Dictionary, enkephalin, leucine-2-alanine



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