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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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$64.70
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$210.00
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$359.00
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$1,440.00

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1 MG
$64.70
5 MG
$210.00
10 MG
$359.00
50 MG
$1,440.00

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

$64.70

In StockDetails

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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.[1] 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.[2]

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 [1]
  • for the determination of the suppression of contraction by opioid receptors [3]
  • to determine whether the peripheral application of DAMGO suppresses the hypertonic saline (HS)-induced masseter nociception in slightly anaesthetized rats [4]

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)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG3203
BCCD3810
BCBW8370
BCBT7410
BCBP2032V

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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
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
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
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
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
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