Endomorphin 2

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

MedKoo CAT#: 597723

CAS#: 141801-26-5

Description: Endomorphin 2 is an endogenous opioid peptide and one of the two endomorphins. It is a high affinity, highly selective agonist of the μ-opioid receptor, and along with endomorphin-1 (EM-1), has been proposed to be the actual endogenous ligand of this receptor (that is, rather than the endorphins).

Chemical Structure

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Endomorphin 2
CAS# 141801-26-5
Instruction

Theoretical Analysis

MedKoo Cat#: 597723
Name: Endomorphin 2
CAS#: 141801-26-5
Chemical Formula: C32H37N5O5
Exact Mass: 571.28
Molecular Weight: 571.670
Elemental Analysis: C, 67.23; H, 6.52; N, 12.25; O, 13.99

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Endomorphin 2; Tyr-Pro-Phe-Phe-NH2;

IUPAC/Chemical Name: (S)-1-(L-tyrosyl)-N-((S)-1-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)pyrrolidine-2-carboxamide

InChi Key: XIJHWXXXIMEHKW-LJWNLINESA-N

InChi Code: InChI=1S/C32H37N5O5/c33-25(18-23-13-15-24(38)16-14-23)32(42)37-17-7-12-28(37)31(41)36-27(20-22-10-5-2-6-11-22)30(40)35-26(29(34)39)19-21-8-3-1-4-9-21/h1-6,8-11,13-16,25-28,38H,7,12,17-20,33H2,(H2,34,39)(H,35,40)(H,36,41)/t25-,26-,27-,28-/m0/s1

SMILES Code: O=C(N)[C@H](CC1=CC=CC=C1)NC([C@H](CC2=CC=CC=C2)NC([C@H]3N(C([C@H](CC4=CC=C(O)C=C4)N)=O)CCC3)=O)=O

Appearance: Solid powder

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: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 571.67 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Wang ZL, Fang Q, Han ZL, Pan JX, Li XH, Li N, Tang HH, Wang P, Zheng T, Chang XM, Wang R. Opposite effects of neuropeptide FF on central antinociception induced by endomorphin-1 and endomorphin-2 in mice. PLoS One. 2014 Aug 4;9(8):e103773. doi: 10.1371/journal.pone.0103773. eCollection 2014. PubMed PMID: 25090615; PubMed Central PMCID: PMC4121275.

2: Li JP, Zhang T, Gao CJ, Kou ZZ, Jiao XW, Zhang LX, Wu ZY, He ZY, Li YQ. Neurochemical features of endomorphin-2-containing neurons in the submucosal plexus of the rat colon. World J Gastroenterol. 2015 Sep 14;21(34):9936-44. doi: 10.3748/wjg.v21.i34.9936. PubMed PMID: 26379398; PubMed Central PMCID: PMC4566386.

3: Zhao XH, Zhao YQ, Zhu C, Chen L, Hu W, Zhang T, Dong YL, Wu SX, Kaye AD, Wang W, Li YQ. Different analgesic effects of intrathecal endomorphin-2 on thermal hyperalgesia and evoked inflammatory pain in ovariectomized rats. Pain Physician. 2015 Mar-Apr;18(2):195-205. PubMed PMID: 25794206.

4: De Marco R, Janecka A. Strategies to Improve Bioavailability and In Vivo Efficacy of the Endogenous Opioid Peptides Endomorphin-1 and Endomorphin-2. Curr Top Med Chem. 2015;16(2):141-55. Review. PubMed PMID: 26279081.

5: Wang CL, Diao YX, Xiang Q, Ren YK, Gu N. Diabetes attenuates the inhibitory effects of endomorphin-2, but not endomorphin-1 on gastrointestinal transit in mice. Eur J Pharmacol. 2014 Sep 5;738:1-7. doi: 10.1016/j.ejphar.2014.05.025. Epub 2014 May 27. PubMed PMID: 24876054.

6: Chen YB, Huang FS, Fen B, Yin JB, Wang W, Li YQ. Inhibitory effects of endomorphin-2 on excitatory synaptic transmission and the neuronal excitability of sacral parasympathetic preganglionic neurons in young rats. Front Cell Neurosci. 2015 May 28;9:206. doi: 10.3389/fncel.2015.00206. eCollection 2015. PubMed PMID: 26074773; PubMed Central PMCID: PMC4446531.

7: Wang CL, Xiang Q, Diao YX, Ren YK, Gu N. Differential antinociceptive effects of intrathecal administration of C-terminal esterified endomorphin-2 analogues in mice. Eur J Pain. 2014 Sep;18(8):1157-64. doi: 10.1002/j.1532-2149.2014.00462.x. Epub 2014 Feb 21. PubMed PMID: 24677379.

8: Perlikowska R, Piekielna J, Mazur M, Koralewski R, Olczak J, do Rego JC, Fichna J, Modranka J, Janecki T, Janecka A. Antinociceptive and antidepressant-like action of endomorphin-2 analogs with proline surrogates in position 2. Bioorg Med Chem. 2014 Sep 1;22(17):4803-9. doi: 10.1016/j.bmc.2014.06.056. Epub 2014 Jul 9. PubMed PMID: 25047937.

9: Chen L, Wang K, Yang T, Wang W, Mei XP, Zhu C, Wang W, Zhang FX, Li YQ. Downregulation of spinal endomorphin-2 correlates with mechanical allodynia in a rat model of tibia cancer. Neuroscience. 2015 Feb 12;286:151-61. doi: 10.1016/j.neuroscience.2014.11.049. Epub 2014 Nov 29. PubMed PMID: 25457129.

10: Rivero G, Llorente J, McPherson J, Cooke A, Mundell SJ, McArdle CA, Rosethorne EM, Charlton SJ, Krasel C, Bailey CP, Henderson G, Kelly E. Endomorphin-2: a biased agonist at the μ-opioid receptor. Mol Pharmacol. 2012 Aug;82(2):178-88. doi: 10.1124/mol.112.078659. Epub 2012 May 2. PubMed PMID: 22553358; PubMed Central PMCID: PMC3400840.

11: Kumar A, Storman EM, Liu NJ, Gintzler AR. Estrogens Suppress Spinal Endomorphin 2 Release in Female Rats in Phase with the Estrous Cycle. Neuroendocrinology. 2015;102(1-2):33-43. doi: 10.1159/000430817. Epub 2015 Apr 29. PubMed PMID: 25925013; PubMed Central PMCID: PMC4575620.

12: Brunetti L, Ferrante C, Orlando G, Recinella L, Leone S, Chiavaroli A, Di Nisio C, Shohreh R, Manippa F, Ricciuti A, Mollica A, Vacca M. Orexigenic effects of endomorphin-2 (EM-2) related to decreased CRH gene expression and increased dopamine and norepinephrine activity in the hypothalamus. Peptides. 2013 Oct;48:83-8. doi: 10.1016/j.peptides.2013.07.021. Epub 2013 Aug 3. PubMed PMID: 23916912.

13: Piekielna J, Kluczyk A, Gentilucci L, Cerlesi MC, Calo' G, Tomböly C, Łapiński K, Janecki T, Janecka A. Ring size in cyclic endomorphin-2 analogs modulates receptor binding affinity and selectivity. Org Biomol Chem. 2015 Jun 7;13(21):6039-46. doi: 10.1039/c5ob00565e. PubMed PMID: 25948019.

14: Perlikowska R, Malfacini D, Cerlesi MC, Calo' G, Piekielna J, Floriot L, Henry T, do-Rego JC, Tömböly C, Kluczyk A, Janecka A. Pharmacological characterization of endomorphin-2-based cyclic pentapeptides with methylated phenylalanine residues. Peptides. 2014 May;55:145-50. doi: 10.1016/j.peptides.2014.03.001. Epub 2014 Mar 13. PubMed PMID: 24632335.

15: Kawabe T, Ueyama T, Hano T, Sapru HN. Cardiovascular responses to microinjections of endomorphin-2 into the nucleus of the solitary tract are attenuated in the spontaneously hypertensive rat. Clin Exp Hypertens. 2015;37(3):197-206. doi: 10.3109/10641963.2014.933969. Epub 2014 Jul 22. PubMed PMID: 25051156.

16: Kumar A, Liu NJ, Madia PA, Gintzler AR. Contribution of Endogenous Spinal Endomorphin 2 to Intrathecal Opioid Antinociception in Rats Is Agonist Dependent and Sexually Dimorphic. J Pain. 2015 Nov;16(11):1200-10. doi: 10.1016/j.jpain.2015.08.003. Epub 2015 Sep 2. PubMed PMID: 26342648; PubMed Central PMCID: PMC5087106.

17: Wu XN, Zhang T, Qian NS, Guo XD, Yang HJ, Huang KB, Luo GQ, Xiang W, Deng WT, Dai GH, Peng KR, Pan SY. Antinociceptive effects of endomorphin-2: suppression of substance P release in the inflammatory pain model rat. Neurochem Int. 2015 Mar;82:1-9. doi: 10.1016/j.neuint.2015.01.004. Epub 2015 Feb 7. PubMed PMID: 25661513.

18: Wu FX, He Y, Di HT, Sun YM, Pan RR, Yu WF, Liu R. An Engineered Endomorphin-2 Gene for Morphine Withdrawal Syndrome. PLoS One. 2016 Mar 22;11(3):e0149877. doi: 10.1371/journal.pone.0149877. eCollection 2016. PubMed PMID: 27003293; PubMed Central PMCID: PMC4803333.

19: Wu F, Xu X, Miao X, Chen J, Sun Y, Yu W. Effect of recombinant adenovirus coding for endomorphin-2 on neuropathic pain in rats. Int J Clin Exp Pathol. 2012;5(9):914-23. Epub 2012 Oct 20. PubMed PMID: 23119108; PubMed Central PMCID: PMC3484491.

20: Paldy E, Borcel E, Higuera-Matas A, López-Montoya G, Wenger T, Toth G, Borsodi A, Ambrosio E. CNR1 gene deletion affects the density of endomorphin-2 binding sites in the mouse brain in a hemisphere-specific manner. Eur J Pharmacol. 2013 Jan 5;698(1-3):220-7. doi: 10.1016/j.ejphar.2012.10.043. Epub 2012 Nov 6. PubMed PMID: 23142371.