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DAMGO

IUPAC name (2S)-2-[[2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl) propanoyl]amino]propanoyl]amino]acetyl]-methylamino]- N-(2-hydroxyethyl)-3-phenylpropanamide
Other names Ala²-MePhe⁴-Glyol⁵-Enkephalin, DAGO, DAMGE
Identifiers
CAS number	78123-71-4
PubChem	5462471
ChemSpider	4575423
ChEMBL	CHEMBL38874^Y
IUPHAR ligand	1647
Jmol-3D images	Image 1
SMILES C[C@@H](NC([C@@H](N)CC1=CC=C(O)C=C1)=O)C(NCC(N([C@H](C(NCCO)=O)CC2=CC=CC=C2)C)=O)=O
InChI InChI=1S/C26H35N5O6/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/h3-11,17,21-22,32-33H,12-16,27H2,1-2H3,(H,28,37)(H,29,35)(H,30,36)/t17-,21+,22+/m1/s1 Key: HPZJMUBDEAMBFI-WTNAPCKOSA-N InChI=1/C26H35N5O6/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/h3-11,17,21-22,32-33H,12-16,27H2,1-2H3,(H,28,37)(H,29,35)(H,30,36)/t17-,21+,22+/m1/s1 Key: HPZJMUBDEAMBFI-WTNAPCKOBV
Properties
Molecular formula	C₂₆H₃₅N₅O₆
Molar mass	513.59 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

DAMGO ([D-Ala², N-MePhe⁴, Gly-ol]-enkephalin) is a synthetic opioid peptide with high μ-opioid receptor specificity. It was synthesized as a biologically stable analog of δ-opioid receptor-preferring endogenous opioids, leu- and met-enkephalin.^[1]

Its structure is H-Tyr-D-Ala-Gly-N-MePhe-Gly-OH.

DAMGO has been used in experimental settings for the possibility of alleviating or reducing opiate tolerance for patients under the treatment of an opioid. Such treatment on rats, adding DAMGO to morphine administration, showed that after seven days morphine had as much of an effect at the same dosage as the first day when administered together with DAMGO to the rats.^[2]

References [edit]

^ Handa BK, Land AC, Lord JA, Morgan BA, Rance MJ, Smith CF. "Analogues of β-LPH61–64 possessing selective agonist activity at μ-opiate receptors." European Journal of Pharmacology. 1981 Apr 9;70(4):531-40. PMID 6263640. doi:10.1016/0014-2999(81)90364-2
^ http://www.unisci.com/stories/20021/0125025.htm Reducing Tolerance To Morphine Could Aid Pain Therapy. Endocytosis of the Mu Opioid Receptor Reduces Tolerance And a Cellular Hallmark of Opiate Withdrawal, A.K. Finn and J. Whistler, Neuron Vol. No. 32 [2001] 829-839

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DAMGO

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