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E7384

Sigma-Aldrich

[D-Ala2, N-Me-Phe4, Gly5-ol]-Enkephalin acetate salt

≥97% (HPLC)

Synonyme(s) :

DAGO, DAMGO, Tyr-D-Ala-Gly-N-methyl-Phe-Gly-ol

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About This Item

Formule empirique (notation de Hill):
C26H35N5O6
Numéro CAS:
100929-53-1
Poids moléculaire :
513.59
Numéro MDL:
MFCD00133215
Code UNSPSC :
12352209
ID de substance PubChem :
329799071
Nomenclature NACRES :
NA.32

Pureté

≥97% (HPLC)

Température de stockage

−20°C

Chaîne SMILES 

CC(O)=O.C[C@@H](NC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)NCC(=O)N(C)[C@@H](Cc2ccccc2)C(=O)NCCO

InChI

1S/C26H35N5O6.C2H4O2/c1-17(30-25(36)21(27)14-19-8-10-20(33)11-9-19)24(35)29-16-23(34)31(2)22(26(37)28-12-13-32)15-18-6-4-3-5-7-18;1-2(3)4/h3-11,17,21-22,32-33H,12-16,27H2,1-2H3,(H,28,37)(H,29,35)(H,30,36);1H3,(H,3,4)/t17-,21+,22+;/m1./s1

Clé InChI

XZZYKCKUDLGXJA-NJUGUJQKSA-N

Informations sur le gène

human ... OPRM1(4988)
mouse ... OPRM1(18390)
rat ... OPRM1(25601)

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Amino Acid Sequence

Tyr-Ala-Gly-Nme-Phe-Gly-ol

Description générale

[D-Ala2, N-Me-Phe4, Gly5-ol]-Enkephalin acetate salt or DAMGO is a full agonist of the μ-opioid receptor. μ-opioid receptor is encoded by the OPRM1 gene, which has a predominant expression in reward-processing areas of brain. It acts as a receptor for endogenous opioids such as β-endorphin, encephalin, as well as foreign opioids such as morphine, heroin, and methadone.

Application

[D-Ala2, N-Me-Phe4, Gly5-ol]-Enkephalin acetate salt or DAMGO has been used:
  • for use as a positive control in the assay of G-protein activation with μ-opioid receptor, to assay the inhibition of cAMP inhibition by DAMGO
  • for the determination of the suppression of contraction by opioid receptors
  • to determine whether the peripheral application of DAMGO suppresses the hypertonic saline (HS)-induced masseter nociception in slightly anaesthetized rats

Actions biochimiques/physiologiques

Enkephalin analog that is a selective agonist at μ-opioid receptors.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Autres remarques

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Frank J Meye et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 32(46), 16120-16128 (2012-11-16)
μ-Opioid receptors (MORs) in the ventral tegmental area (VTA) are pivotally involved in addictive behavior. While MORs are typically activated by opioids, they can also become constitutively active in the absence of any agonist. In the current study, we present
Javier Llorente et al.
The European journal of neuroscience, 36(12), 3636-3642 (2012-09-26)
There is considerable controversy over whether μ-opioid receptor (MOPr) desensitization is homologous or heterologous and over the mechanisms underlying such desensitization. In different cell types MOPr desensitization has been reported to involve receptor phosphorylation by various kinases, including G-protein-coupled receptor
Raza Qazi et al.
Nature biomedical engineering, 3(8), 655-669 (2019-08-07)
Both in vivo neuropharmacology and optogenetic stimulation can be used to decode neural circuitry, and can provide therapeutic strategies for brain disorders. However, current neuronal interfaces hinder long-term studies in awake and freely behaving animals, as they are limited in
Ken W K Lee et al.
Journal of psychiatry & neuroscience : JPN, 40(1), 38-45 (2014-10-01)
Preference for fatty foods is a risk factor for obesity. It is a complex behaviour that involves the brain reward system and is regulated by genetic and environmental factors, such as the opioid receptor mu-1 gene (OPRM1) and prenatal exposure
B Driessen et al.
British journal of pharmacology, 108(2), 443-447 (1993-02-01)
1. Effects of opioid agonists on the purinergic and adrenergic components of neurogenic contractions and in some experiments on transmitter overflow were studied in the mouse isolated vas deferens. 2. When the vas deferens was stimulated every 2 min by
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