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Merck
CN

E7384

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

≥97% (HPLC), μ-opioid receptors agonist

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
UNSPSC Code:
12352209
PubChem Substance ID:
329799071
NACRES:
NA.32
MDL number:
MFCD00133215

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Product Name

[D-Ala2, N-Me-Phe4, Gly5-ol]-Enkephalin acetate salt, ≥97% (HPLC)

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 key

XZZYKCKUDLGXJA-NJUGUJQKSA-N

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

assay

≥97% (HPLC)

storage temp.

−20°C

Quality Level

100

Gene Information

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

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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.

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.

Other Notes

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM7967
BCCG3203
BCCD3810
BCBW8370
BCBT7410

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Jami L Saloman et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 36(42), 10769-10781 (2016-11-01)
Designer receptors exclusively activated by designer drugs (DREADDs) are an advanced experimental tool that could potentially provide a novel approach to pain management. In particular, expression of an inhibitory (Gi-coupled) DREADD in nociceptors might enable ligand-dependent analgesia. To test this
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
Mariana Spetea et al.
British journal of pharmacology, 174(15), 2444-2456 (2017-05-12)
The κ receptor has a central role in modulating neurotransmission in central and peripheral neuronal circuits that subserve pain and other behavioural responses. Although κ receptor agonists do not produce euphoria or lead to respiratory suppression, they induce dysphoria and
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
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
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