DAMGO | CAS#78123-71-4 | mu opioid receptor agonist

MedKoo Cat#: 145417 | Name: DAMGO

Description:

WARNING: This product is for research use only, not for human or veterinary use.

DAMGO is a selective mu opioid receptor agonist. DAMGO displays a triad of opioid-like effects. DAMGO decreases the amplitude of both evoked excitatory postsynaptic currents (eEPSCs) and inhibitory postsynaptic currents (eIPSCs), and also decreases the frequency of both miniature EPSCs and IPSCs without effect on the amplitude. DAMGO decreases the frequency of sEPSCs in pyramidal cells of BLA.

Chemical Structure

DAMGO

CAS#78123-71-4

Theoretical Analysis

MedKoo Cat#: 145417

Name: DAMGO

CAS#: 78123-71-4

Chemical Formula: C26H35N5O6

Exact Mass: 513.2587

Molecular Weight: 513.60

Elemental Analysis: C, 60.80; H, 6.87; N, 13.64; O, 18.69

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

DAMGO;

IUPAC/Chemical Name

(S)-2-amino-N-((R)-1-((2-(((S)-1-((2-hydroxyethyl)amino)-1-oxo-3-phenylpropan-2-yl)(methyl)amino)-2-oxoethyl)amino)-1-oxopropan-2-yl)-3-(4-hydroxyphenyl)propanamide

InChi Key

HPZJMUBDEAMBFI-WTNAPCKOSA-N

InChi Code

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

SMILES Code

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 513.60 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Ma X, Chen R, Huang M, Wang W, Luo L, Kim DK, Jiang W, Xu T. DAMGO-induced μ opioid receptor internalization and recycling restore morphine sensitivity in tolerant rat. Eur J Pharmacol. 2020 Jul 5;878:173118. doi: 10.1016/j.ejphar.2020.173118. Epub 2020 Apr 19. PMID: 32320702. 2: Li N, Xiao J, Niu J, Zhang M, Shi Y, Yu B, Zhang Q, Chen D, Zhang N, Fang Q. Synergistic interaction between DAMGO-NH2 and NOP01 in peripherally acting antinociception in two mouse models of formalin pain. Peptides. 2023 Mar;161:170943. doi: 10.1016/j.peptides.2023.170943. Epub 2023 Jan 6. PMID: 36621672. 3: Zhang W, Yang HL, Song JJ, Chen M, Dong Y, Lai B, Yu YG, Ma L, Zheng P. DAMGO depresses inhibitory synaptic transmission via different downstream pathways of μ opioid receptors in ventral tegmental area and periaqueductal gray. Neuroscience. 2015 Aug 20;301:144-54. doi: 10.1016/j.neuroscience.2015.05.077. Epub 2015 Jun 3. PMID: 26047721. 4: Gold MS, Levine JD. DAMGO inhibits prostaglandin E2-induced potentiation of a TTX-resistant Na+ current in rat sensory neurons in vitro. Neurosci Lett. 1996 Jul 12;212(2):83-6. doi: 10.1016/0304-3940(96)12791-9. PMID: 8832644. 5: Harris HM, Eans SO, Ganno ML, Davis JC, Dooley CT, McLaughlin JP, Nefzi A. Antinociceptive activity of thiazole-containing cyclized DAMGO and Leu-(Met) enkephalin analogs. Org Biomol Chem. 2019 Jun 7;17(21):5305-5315. doi: 10.1039/c9ob00882a. Epub 2019 May 16. PMID: 31094391; PMCID: PMC6637423. 6: Zhang RX, Zhang M, Li A, Pan L, Berman BM, Ren K, Lao L. DAMGO in the central amygdala alleviates the affective dimension of pain in a rat model of inflammatory hyperalgesia. Neuroscience. 2013 Nov 12;252:359-66. doi: 10.1016/j.neuroscience.2013.08.030. Epub 2013 Aug 28. PMID: 23994597; PMCID: PMC3864641. 7: Dziedowiec E, Nayak SU, Gruver KS, Jennings T, Tallarida CS, Rawls SM. Mu Opioid Receptor Agonist DAMGO Produces Place Conditioning, Abstinence-induced Withdrawal, and Naltrexone-Dependent Locomotor Activation in Planarians. Neuroscience. 2018 Aug 21;386:214-222. doi: 10.1016/j.neuroscience.2018.06.029. Epub 2018 Jun 27. PMID: 29958944; PMCID: PMC6086122. 8: Khoramjouy M, Ahmadi F, Faizi M, Shahhosseini S. Optimization binding studies of opioid receptors, saturation and competition, using [3H]-DAMGO. Pharmacol Rep. 2021 Oct;73(5):1390-1395. doi: 10.1007/s43440-021-00265-9. Epub 2021 Apr 19. PMID: 33871815. 9: Honda E, Ono K, Inenaga K. DAMGO suppresses both excitatory and inhibitory synaptic transmission in supraoptic neurones of mouse hypothalamic slice preparations. J Neuroendocrinol. 2004 Mar;16(3):198-207. doi: 10.1111/j.0953-8194.2004.01151.x. PMID: 15049850. 10: Yang J, Yang H, Du X, Ma Q, Song J, Chen M, Dong Y, Ma L, Zheng P. Morphine and DAMGO produce an opposite effect on presynaptic glutamate release via different downstream pathways of μ opioid receptors in the basolateral amygdala. Neuropharmacology. 2014 Nov;86:353-61. doi: 10.1016/j.neuropharm.2014.08.021. Epub 2014 Sep 6. PMID: 25196735. 11: Smith HS. Peripherally-acting opioids. Pain Physician. 2008 Mar;11(2 Suppl):S121-32. PMID: 18443636. 12: Onogi T, Minami M, Katao Y, Nakagawa T, Aoki Y, Toya T, Katsumata S, Satoh M. DAMGO, a mu-opioid receptor selective agonist, distinguishes between mu- and delta-opioid receptors around their first extracellular loops. FEBS Lett. 1995 Jan 2;357(1):93-7. doi: 10.1016/0014-5793(94)01341-w. PMID: 8001688. 13: Steffens H, Schomburg ED. Spinal motor actions of the μ-opioid receptor agonist DAMGO in the cat. Neurosci Res. 2011 May;70(1):44-54. doi: 10.1016/j.neures.2011.01.011. Epub 2011 Jan 27. PMID: 21276826. 14: Lindqvist A, Rip J, Gaillard PJ, Björkman S, Hammarlund-Udenaes M. Enhanced brain delivery of the opioid peptide DAMGO in glutathione pegylated liposomes: a microdialysis study. Mol Pharm. 2013 May 6;10(5):1533-41. doi: 10.1021/mp300272a. Epub 2012 Sep 14. PMID: 22934681. 15: Koganezawa T, Okada Y, Terui N, Paton JF, Oku Y. A μ-opioid receptor agonist DAMGO induces rapid breathing in the arterially perfused in situ preparation of rat. Respir Physiol Neurobiol. 2011 Jul 31;177(2):207-11. doi: 10.1016/j.resp.2011.04.002. Epub 2011 Apr 13. PMID: 21513819. 16: Yan JB, Sun HL, Wang Q, Chen K, Sun B, Song L, Yan W, Zhao XL, Zhao SR, Zhang Y, Qiao H, Hu B, Yan JQ. Natriorexigenic effect of DAMGO is decreased by blocking AT1 receptors in the central nucleus of the amygdala. Neuroscience. 2014 Mar 14;262:9-20. doi: 10.1016/j.neuroscience.2013.12.046. Epub 2013 Dec 31. PMID: 24389419. 17: Bailey CP, Couch D, Johnson E, Griffiths K, Kelly E, Henderson G. Mu-opioid receptor desensitization in mature rat neurons: lack of interaction between DAMGO and morphine. J Neurosci. 2003 Nov 19;23(33):10515-20. doi: 10.1523/JNEUROSCI.23-33-10515.2003. PMID: 14627635; PMCID: PMC6740932. 18: Lindqvist A, Jansson B, Hammarlund-Udenaes M. Quantitative analysis of the opioid peptide DAMGO in rat plasma and microdialysis samples using liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jul 1;900:11-7. doi: 10.1016/j.jchromb.2012.05.014. Epub 2012 May 18. PMID: 22672845. 19: Jennings EM, Sullivan LC, Jamshidi RJ, LoCoco PM, Smith HR, Chavera TS, Berg KA, Clarke WP. Age-related changes in peripheral nociceptor function. Neuropharmacology. 2022 Sep 15;216:109187. doi: 10.1016/j.neuropharm.2022.109187. Epub 2022 Jul 12. PMID: 35835212. 20: Zhao GM, Qian X, Schiller PW, Szeto HH. Comparison of [Dmt1]DALDA and DAMGO in binding and G protein activation at mu, delta, and kappa opioid receptors. J Pharmacol Exp Ther. 2003 Dec;307(3):947-54. doi: 10.1124/jpet.103.054775. Epub 2003 Oct 8. PMID: 14534366.