DAMGO

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] The crystal structure of DAMGO bound to the µ opioid receptor reveals a very similar binding pose to morphinans.[2]

DAMGO

Names
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 Ala^2-MePhe^4-Glyol^5-Enkephalin, DAGO, DAMGE
Identifiers
CAS Number	78123-71-4^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL38874^Y
ChemSpider	4575423^N
IUPHAR/BPS	1647
PubChem CID	5462471
CompTox Dashboard (EPA)	DTXSID30228775
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^N Key: HPZJMUBDEAMBFI-WTNAPCKOSA-N^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
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
Properties
Chemical formula	C26H35N5O6
Molar mass	513.595 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

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.[3][4][5]

See also

• DADLE
• DPDPE
• Morphiceptin
• PTI-609

References

1. Handa, Balraj K.; Lane, Anthony C.; Lord, John A.H.; Morgan, Barry A.; Rance, Michael J.; Smith, Colin F.C. (1981). "Analogues of β-LPH61–64 possessing selective agonist activity at μ-opiate receptors". European Journal of Pharmacology. 70 (4): 531. doi:10.1016/0014-2999(81)90364-2. PMID 6263640.
2. Koehl, Antoine; Hu, Hongli; Maeda, Shoji; Zhang, Yan; Qu, Qianhui; Paggi, Joseph M.; Latorraca, Naomi R.; Hilger, Daniel; Dawson, Roger; Matile, Hugues; Schertler, Gebhard F. X. (2018-06-13). "Structure of the µ-opioid receptor–Gi protein complex". Nature. 558 (7711): 547–552. doi:10.1038/s41586-018-0219-7. ISSN 0028-0836. PMC 6317904. PMID 29899455.CS1 maint: PMC format (link)
3. "Reducing Tolerance To Morphine Could Aid Pain Therapy".
4. A.K. Finn and J. Whistler (2001). "Endocytosis of the Mu Opioid Receptor Reduces Tolerance And a Cellular Hallmark of Opiate Withdrawal". Neuron. 32 (5): 829–839. doi:10.1016/s0896-6273(01)00517-7. PMID 11738029.
5. He, Li; Fong, Jamie; von Zastrow, Mark; Whistler, Jennifer L (2002). "Regulation of Opioid Receptor Trafficking and Morphine Tolerance by Receptor Oligomerization". Cell. 108 (2): 271. doi:10.1016/S0092-8674(02)00613-X. PMID 11832216.