DAMGO

Short description: Synthetic opioid peptide

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

Ala2-MePhe4-Glyol5-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

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

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] Structures of DAMGO bound to the µ opioid receptor reveal a very similar binding pose to morphinans.[2][3]

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.[4][5][6]

## See also

* DADLE
* DPDPE
* Morphiceptin

## References

1. ↑ "Analogues of β-LPH61–64 possessing selective agonist activity at μ-opiate receptors". European Journal of Pharmacology 70 (4): 531–40. April 1981. doi:10.1016/0014-2999(81)90364-2. PMID 6263640.
2. ↑ "Structure of the µ-opioid receptor–Gi". Nature 558 (7711): 547–552. June 2018. doi:10.1038/s41586-018-0219-7. PMID 29899455.
3. ↑ Zhuang, Youwen; Wang, Yue; He, Bingqing; He, Xinheng; Zhou, X. Edward; Guo, Shimeng; Rao, Qidi; Yang, Jiaqi et al. (2022-11-10). "Molecular recognition of morphine and fentanyl by the human μ-opioid receptor" (in en). Cell 185 (23): 4361–4375.e19. doi:10.1016/j.cell.2022.09.041. PMID 36368306.
4. ↑ Radler, Don (25 January 2002). "Reducing Tolerance To Morphine Could Aid Pain Therapy". Daily University Science News (UniSci). UniScience News Net, Inc.. http://www.unisci.com/stories/20021/0125025.htm.
5. ↑ "Endocytosis of the Mu Opioid Receptor Reduces Tolerance and a Cellular Hallmark of Opiate Withdrawal". Neuron 32 (5): 829–839. December 2001. doi:10.1016/S0896-6273(01)00517-7. PMID 11738029.
6. ↑ "Regulation of Opioid Receptor Trafficking and Morphine Tolerance by Receptor Oligomerization". Cell 108 (2): 271–82. January 2002. doi:10.1016/S0092-8674(02)00613-X. PMID 11832216.

* v
* t
* e

Opioid receptor modulators

MOR|

* Agonists (abridged; see here for a full list): 3-HO-PCP
* 7-Acetoxymitragynine
* 7-Hydroxymitragynine
* ψ-Akuammigine
* α-Chlornaltrexamine
* α-Narcotine
* Acetyldihydrocodeine
* Acetylfentanyl
* Acrylfentanyl
* Adrenorphin (metorphamide)
* AH-7921
* Akuammicine
* Akuammidine
* Alfentanil
* Anileridine
* Apparicine
* β-Endorphin
* BAM-12P
* BAM-18P
* BAM-22P
* Benzhydrocodone
* Benzylmorphine
* Bezitramide
* Biphalin
* BU08070
* Buprenorphine
* Butorphan
* Butorphanol
* Butyrfentanyl
* BW373U86
* Carfentanil
* Casokefamide
* Cebranopadol
* Chloroxymorphamine
* Codeine
* DADLE
* DAMGO (DAGO)
* Dermorphin
* Desmetramadol (desmethyltramadol)
* Desomorphine
* Dextromoramide
* Dextropropoxyphene (propoxyphene)
* Dezocine
* Dimenoxadol
* Dimethylaminopivalophenone
* Eluxadoline
* Diamorphine (heroin)
* Dihydrocodeine
* Dihydroetorphine
* Dihydromorphine
* Dinalbuphine sebacate
* Diphenoxylate
* Dipipanone
* Dynorphin A
* Embutramide
* Endomorphin-1
* Endomorphin-2
* Eseroline
* Ethylmorphine
* Etorphine
* Fentanyl
* Fluorophen
* Frakefamide
* Furanylfentanyl
* Hemorphin-4
* Herkinorin
* Hodgkinsine
* Hydrocodone
* Hydromorphinol
* Hydromorphone
* IBNtxA
* Ketamine
* Ketobemidone
* Kratom
* Laudanosine
* Lefetamine
* Leu-enkephalin
* Levacetylmethadol
* Levomethorphan
* Levorphanol
* Lexanopadol
* Loperamide
* Loxicodegol
* Matrine
* Meptazinol
* Met-enkephalin (metenkefalin)
* Methadone
* Metkefamide
* Metopon
* Mitragynine
* Mitragynine pseudoindoxyl
* Morphiceptin
* Morphine
* Nalbuphine
* NalBzOH
* Nalmexone
* Naltalimide
* Neopine
* NFEPP
* Nicocodeine
* Nicodicodine
* Nicomorphine
* NKTR-181
* Norketamine
* Octreotide
* Oliceridine
* OM-3-MNZ
* Oripavine
* Oxycodone
* Oxymorphazone
* Oxymorphonazine
* Oxymorphone
* Oxymorphone phenylhydrazone
* OxyPNPH
* Papaver somniferum (opium)
* Pentazocine
* Pericine
* Pethidine (meperidine)
* Phenazocine
* Phencyclidine
* Piminodine
* Piritramide
* PL-017
* Prodine
* Propiram
* PZM21
* Racemethorphan
* Racemorphan
* Remifentanil
* Salsolinol
* SC-17599
* Sinomenine
* Sufentanil
* Tapentadol
* Tetrahydropapaveroline
* TH-030418
* Thebaine
* Thienorphine
* Tianeptine
* Tilidine
* Tramadol
* Trimebutine
* TRIMU 5
* TRV734
* Tubotaiwine
* U-47700
* Valorphin
* Viminol
* Xorphanol

* PAMs: BMS-986121
* BMS-986122

* Antagonists: (3S,4S)-Picenadol
* 2-(S)-N,N-(R)-Viminol
* 3CS-nalmefene
* 4-Caffeoyl-1,5-quinide
* 4′-Hydroxyflavanone
* 4',7-Dihydroxyflavone
* 6β-Naltrexol
* 6β-Naltrexol-d4
* 18-MC
* α-Gliadin
* β-Chlornaltrexamine
* β-Funaltrexamine
* Akuammine
* Alvimopan
* AM-251
* Apigenin
* AT-076
* Axelopran
* Bevenopran
* Catechin
* Catechin gallate
* Clocinnamox
* CTAP
* CTOP
* Cyclofoxy
* Cyprodime
* Diacetylnalorphine
* Diprenorphine
* ECG
* EGC
* Epicatechin
* Eptazocine
* Gemazocine
* Ginsenoside R
* Hyperoside
* Ibogaine
* Levallorphan
* Lobeline
* LY-255582
* LY-2196044
* Methocinnamox
* Methylnaltrexone
* Methylsamidorphan chloride
* Naldemedine
* Nalmefene
* Nalodeine (N-allylnorcodeine)
* Nalorphine
* Nalorphine dinicotinate
* Naloxazone
* Naloxegol
* Naloxol
* Naloxonazine
* Naloxone
* Naltrexazone
* Naltrexonazine
* Naltrexone
* Naltrindole
* Naringenin
* Noribogaine
* Oxilorphan
* Pawhuskin A
* Rimonabant
* Quadazocine
* Samidorphan
* Taxifolin

* Unknown/unsorted: Cannabidiol
* Coronaridine
* Cyproterone acetate
* Dihydroakuuamine
* Tabernanthine
* Tetrahydrocannabinol

DOR|

* Agonists: 3CS-nalmefene
* 6'-GNTI
* 7-SIOM
* ADL-5747 (PF-04856881)
* ADL-5859
* Alazocine (SKF-10047)
* Amoxapine
* AR-M100390 (ARM390)
* AZD2327
* β-Endorphin
* BAM-18P
* Biphalin
* BU-48
* Butorphan
* Butorphanol
* BW373U86
* Casokefamide
* Cebranopadol
* Codeine
* Cyclazocine
* DADLE
* Deltorphin A
* Deltorphin I
* Deltorphin II
* Desmethylclozapine
* Desmetramadol (desmethyltramadol)
* Dezocine
* Diamorphine (heroin)
* Dihydroetorphine
* Dihydromorphine
* DPDPE
* DPI-221
* DPI-3290
* DSLET
* Ethylketazocine
* Etorphine
* Fentanyl
* FIT
* Fluorophen
* Hemorphin-4
* Hydrocodone
* Hydromorphone
* Ibogaine
* Isomethadone
* JNJ-20788560
* KNT-127
* Kratom
* Laudanosine
* Leu-enkephalin
* Levomethorphan
* Levorphanol
* Lexanopadol
* Lofentanil
* Met-enkephalin (metenkefalin)
* Metazocine
* Metkefamide
* Mitragynine
* Mitragynine pseudoindoxyl
* Morphine
* N-Phenethyl-14-ethoxymetopon
* Norbuprenorphine
* NalBzOH
* Oripavine
* Oxycodone
* Oxymorphone
* Pethidine (meperidine)
* Proglumide
* Racemethorphan
* Racemorphan
* RWJ-394674
* Samidorphan
* SB-235863
* SNC-80
* SNC-162
* TAN-67 (SB-205,607)
* TH-030418
* Thebaine
* Thiobromadol (C-8813)
* Tonazocine
* Tramadol
* TRV250
* Xorphanol
* Zenazocine

* Antagonists: 4',7-Dihydroxyflavone
* 5'-NTII
* 6β-Naltrexol
* 6β-Naltrexol-d4
* α-Santolol
* β-Chlornaltrexamine
* Apigenin
* AT-076
* Axelopran
* Bevenopran
* BNTX
* Catechin
* Catechin gallate
* Clocinnamox
* Diacetylnalorphine
* Diprenorphine
* ECG
* EGC
* Eluxadoline
* Epicatechin
* ICI-154129
* ICI-174864
* LY-255582
* LY-2196044
* Methylnaltrexone
* Methylnaltrindole
* N-Benzylnaltrindole
* Nalmefene
* Nalorphine
* Naltrexone
* Naltriben
* Naltrindole
* Naloxone
* Naringenin
* Noribogaine
* Pawhuskin A
* Quadazocine
* SDM25N
* SoRI-9409
* Taxifolin
* Thienorphine

* Unknown/unsorted: 18-MC
* Cannabidiol
* Coronaridine
* Cyproterone acetate
* Tabernanthine
* Tetrahydrocannabinol

KOR|

* Agonists: 3CS-nalmefene
* 6'-GNTI
* 8-CAC
* 18-MC
* 14-Methoxymetopon
* β-Chlornaltrexamine
* β-Funaltrexamine
* Adrenorphin (metorphamide)
* Akuuamicine
* Alazocine (SKF-10047)
* Allomatrine
* Apadoline
* Asimadoline
* BAM-12P
* BAM-18P
* BAM-22P
* Big dynorphin
* Bremazocine
* BRL-52537
* Butorphan
* Butorphanol
* BW373U86
* Cebranopadol
* Ciprefadol
* CR665
* Cyclazocine
* Cyclorphan
* Cyprenorphine
* Desmetramadol (desmethyltramadol)
* Diamorphine (heroin)
* Diacetylnalorphine
* Difelikefalin
* Dihydroetorphine
* Dihydromorphine
* Dinalbuphine sebacate
* Diprenorphine
* Dynorphin A
* Dynorphin B (rimorphin)
* Eluxadoline
* Enadoline
* Eptazocine
* Erinacine E
* Ethylketazocine
* Etorphine
* Fedotozine
* Fentanyl
* Gemazocine
* GR-89696
* GR-103545
* Hemorphin-4
* Herkinorin
* HS665
* Hydromorphone
* HZ-2
* Ibogaine
* ICI-199,441
* ICI-204,448
* Ketamine
* Ketazocine
* Laudanosine
* Leumorphin (dynorphin B-29)
* Levallorphan
* Levomethorphan
* Levorphanol
* Lexanopadol
* Lofentanil
* LPK-26
* Lufuradom
* Matrine
* MB-1C-OH
* Menthol
* Metazocine
* Metkefamide
* Mianserin
* Mirtazapine
* Morphine
* Moxazocine
* MR-2034
* N-MPPP
* Nalbuphine
* NalBzOH
* Nalfurafine
* Nalmefene
* Nalodeine (N-allylnorcodeine)
* Nalorphine
* Naltriben
* Niravoline
* Norbuprenorphine
* Norbuprenorphine-3-glucuronide
* Noribogaine
* Norketamine
* Oripavine
* Oxilorphan
* Oxycodone
* Pentazocine
* Pethidine (meperidine)
* Phenazocine
* Proxorphan
* Racemethorphan
* Racemorphan
* RB-64
* Salvinorin A (salvia)
* Salvinorin B ethoxymethyl ether
* Salvinorin B methoxymethyl ether
* Samidorphan
* Spiradoline (U-62,066)
* TH-030418
* Thienorphine
* Tifluadom
* Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline)
* U-50488
* U-54,494A
* U-69,593
* Xorphanol

* Antagonists: 4′-Hydroxyflavanone
* 4',7-Dihydroxyflavone
* 5'-GNTI
* 6'-GNTI
* 6β-Naltrexol
* 6β-Naltrexol-d4
* β-Chlornaltrexamine
* Buprenorphine/samidorphan
* Amentoflavone
* ANTI
* Apigenin
* Arodyne
* AT-076
* Aticaprant
* Axelopran
* AZ-MTAB
* Binaltorphimine
* BU09059
* Buprenorphine
* Catechin
* Catechin gallate
* CERC-501 (LY-2456302)
* Clocinnamox
* Cyclofoxy
* Dezocine
* DIPPA
* EGC
* ECG
* Epicatechin
* Hyperoside
* JDTic
* LY-255582
* LY-2196044
* LY-2444296
* LY-2459989
* LY-2795050
* MeJDTic
* Methylnaltrexone
* ML190
* ML350
* MR-2266
* N-Fluoropropyl-JDTic
* Naloxone
* Naltrexone
* Naltrindole
* Naringenin
* Norbinaltorphimine
* Noribogaine
* Pawhuskin A
* PF-4455242
* RB-64
* Quadazocine
* Taxifolin
* UPHIT
* Zyklophin

* Unknown/unsorted: Akuammicine
* Akuammine
* Coronaridine
* Cyproterone acetate
* Dihydroakuuamine
* Ibogamine
* Tabernanthine

NOP|

* Agonists: (Arg14,Lys15)Nociceptin
* ((pF)Phe4)Nociceptin(1-13)NH2
* (Phe1Ψ(CH2-NH)Gly2)Nociceptin(1-13)NH2
* Ac-RYYRWK-NH2
* Ac-RYYRIK-NH2
* BU08070
* Buprenorphine
* Cebranopadol
* Dihydroetorphine
* Etorphine
* JNJ-19385899
* Levomethorphan
* Levorphanol
* Levorphanol
* Lexanopadol
* MCOPPB
* MT-7716
* NNC 63-0532
* Nociceptin (orphanin FQ)
* Nociceptin (1-11)
* Nociceptin (1-13)NH2
* Norbuprenorphine
* Racemethorphan
* Racemorphan
* Ro64-6198
* Ro65-6570
* SCH-221510
* SCH-486757
* SR-8993
* SR-16435
* TH-030418

* Antagonists: (Nphe1)Nociceptin(1-13)NH2
* AT-076
* BAN-ORL-24
* BTRX-246040 (LY-2940094)
* J-113,397
* JTC-801
* NalBzOH
* Nociceptin (1-7)
* Nocistatin
* SB-612,111
* SR-16430
* Thienorphine
* Trap-101
* UFP-101

Unsorted|

* β-Casomorphins
* Amidorphin
* BAM-20P
* Cytochrophin-4
* Deprolorphin
* Gliadorphin (gluteomorphin)
* Gluten exorphins
* Hemorphins
* Kava constituents
* MEAGL
* MEAP
* NEM
* Neoendorphins
* Nepetalactone (catnip)
* Peptide B
* Peptide E
* Peptide F
* Peptide I
* Rubiscolins
* Soymorphins

Others|

* Enkephalinase inhibitors: Amastatin
* BL-2401
* Candoxatril
* D -Phenylalanine
* Dexecadotril (retorphan)
* Ecadotril (sinorphan)
* Kelatorphan
* Racecadotril (acetorphan)
* RB-101
* RB-120
* RB-3007
* Opiorphan
* Selank
* Semax
* Spinorphin
* Thiorphan
* Tynorphin
* Ubenimex (bestatin)

* Propeptides: β-Lipotropin (proendorphin)
* Prodynorphin
* Proenkephalin
* Pronociceptin
* Proopiomelanocortin (POMC)

* Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)

See also: Receptor/signaling modulators • Signaling peptide/protein receptor modulators

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*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[MOR]: μ-opioid receptor
*[DOR]: δ-opioid receptor
*[KOR]: κ-opioid receptor
*[NOP]: Nociceptin receptor