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E7384

Sigma-Aldrich

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

≥97% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C26H35N5O6
CAS Number:
100929-53-1
Molecular Weight:
513.59
MDL number:
MFCD00133215
UNSPSC Code:
12352209
PubChem Substance ID:
329799071
NACRES:
NA.32

Quality Level

100

assay

≥97% (HPLC)

storage temp.

−20°C

SMILES string

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

InChI key

XZZYKCKUDLGXJA-NJUGUJQKSA-N

Gene Information

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

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Amino Acid Sequence

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

General description

[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

Biochem/physiol Actions

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
Roberta Lattanzi et al.
Frontiers in pharmacology, 9, 1002-1002 (2018-09-21)
Pain, particularly chronic pain, is still an unsolved medical condition. Central goals in pain control are to provide analgesia of adequate efficacy and to reduce complications associated with the currently available drugs. Opioids are the mainstay for the treatment of
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