DAMGO

{{Short description|Synthetic opioid peptide}}

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{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 403686009

| ImageFile = DAMGO Structure.svg

| ImageSize =

| IUPACName = (2S)-2-[[2-[[(2R)-2-[[(2S)-2-Amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]-methylamino]-N-(2-hydroxyethyl)-3-phenylpropanamide

| OtherNames = Ala²-MePhe⁴-Glyol⁵-Enkephalin, DAGO, DAMGE

|Section1={{Chembox Identifiers

| PubChem = 5462471

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4575423

| 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

| InChIKey = HPZJMUBDEAMBFI-WTNAPCKOBV

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = HPZJMUBDEAMBFI-WTNAPCKOSA-N

| IUPHAR_ligand = 1647

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 78123-71-4

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 38874

| 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 }}

|Section2={{Chembox Properties

| C=26 | H=35 | N=5 | O=6

| Appearance =

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|Section3={{Chembox Hazards

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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.{{cite journal | vauthors = Handa BK, Land AC, Lord JA, Morgan BA, Rance MJ, Smith CF | title =Analogues of β-LPH61–64 possessing selective agonist activity at μ-opiate receptors | journal = European Journal of Pharmacology | volume = 70 | issue = 4 | pages = 531–40 | date = April 1981 | pmid = 6263640 | doi = 10.1016/0014-2999(81)90364-2 }} Structures of DAMGO bound to the μ opioid receptor reveal a very similar binding pose to morphinans.{{cite journal | vauthors = Koehl A, Hu H, Maeda S, Zhang Y, Qu Q, Paggi JM, Latorraca NR, Hilger D, Dawson R, Matile H, Schertler GF, Granier S, Weis WI, Dror RO, Manglik A, Skiniotis G, Kobilka BK | title = Structure of the μ-opioid receptor–Gi | journal = Nature | volume = 558 | issue = 7711 | pages = 547–552 | date = June 2018 | pmid = 29899455 | pmc = 6317904 | doi = 10.1038/s41586-018-0219-7 }}{{Cite journal |last1=Zhuang |first1=Youwen |last2=Wang |first2=Yue |last3=He |first3=Bingqing |last4=He |first4=Xinheng |last5=Zhou |first5=X. Edward |last6=Guo |first6=Shimeng |last7=Rao |first7=Qidi |last8=Yang |first8=Jiaqi |last9=Liu |first9=Jinyu |last10=Zhou |first10=Qingtong |last11=Wang |first11=Xiaoxi |last12=Liu |first12=Mingliang |last13=Liu |first13=Weiyi |last14=Jiang |first14=Xiangrui |last15=Yang |first15=Dehua |date=2022-11-10 |title=Molecular recognition of morphine and fentanyl by the human μ-opioid receptor |journal=Cell |language=en |volume=185 |issue=23 |pages=4361–4375.e19 |doi=10.1016/j.cell.2022.09.041|pmid=36368306 |s2cid=253426623 |doi-access=free }}

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

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, whereas a separate control group of rats that were administered the same dosage of morphine over the course of the same week, but without DAMGO, displayed an increased tolerance and lessened analgesic efficacy toward the end of that week.{{cite web | first = Don | last = Radler | url = http://www.unisci.com/stories/20021/0125025.htm | title = Reducing Tolerance To Morphine Could Aid Pain Therapy | date = 25 January 2002 | work = Daily University Science News (UniSci) | publisher = UniScience News Net, Inc. }}{{cite journal | vauthors = Finn AK, Whistler JL | title = Endocytosis of the Mu Opioid Receptor Reduces Tolerance and a Cellular Hallmark of Opiate Withdrawal | journal = Neuron | volume = 32 | issue = 5 | pages = 829–839 | date = December 2001 | pmid = 11738029 | doi = 10.1016/S0896-6273(01)00517-7 | s2cid = 16396686 | doi-access = free }}{{cite journal | vauthors = He L, Fong J, von Zastrow M, Whistler JL | title = Regulation of Opioid Receptor Trafficking and Morphine Tolerance by Receptor Oligomerization | journal = Cell | volume = 108 | issue = 2 | pages = 271–82 | date = January 2002 | pmid = 11832216 | doi = 10.1016/S0092-8674(02)00613-X | s2cid = 15933405 | doi-access = free }}