Endomorphin 1

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

MedKoo CAT#: 597727

CAS#: 189388-22-5

Description: Endomorphin 1 is a μ-opioid receptor antagonist with high affinity. It produces analgesic effects in mammals and is similar in potency to morphine. Pain relief antagonist.

Chemical Structure

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Endomorphin 1
CAS# 189388-22-5
Instruction

Theoretical Analysis

MedKoo Cat#: 597727
Name: Endomorphin 1
CAS#: 189388-22-5
Chemical Formula: C34H38N6O5
Exact Mass: 610.29
Molecular Weight: 610.710
Elemental Analysis: C, 66.87; H, 6.27; N, 13.76; O, 13.10

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 1; Tyr-Pro-Trp-Phe-Nh2;

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

InChi Key: ZEXLJFNSKAHNFH-SYKYGTKKSA-N

InChi Code: InChI=1S/C34H38N6O5/c35-26(17-22-12-14-24(41)15-13-22)34(45)40-16-6-11-30(40)33(44)39-29(19-23-20-37-27-10-5-4-9-25(23)27)32(43)38-28(31(36)42)18-21-7-2-1-3-8-21/h1-5,7-10,12-15,20,26,28-30,37,41H,6,11,16-19,35H2,(H2,36,42)(H,38,43)(H,39,44)/t26-,28-,29-,30-/m0/s1

SMILES Code: O=C(N)[C@H](CC1=CC=CC=C1)NC([C@H](CC2=CNC3=C2C=CC=C3)NC([C@H]4N(C([C@H](CC5=CC=C(O)C=C5)N)=O)CCC4)=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 610.71 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 CL, Qiu TT, Diao YX, Zhang Y, Gu N. Novel endomorphin-1 analogs with C-terminal oligoarginine-conjugation display systemic antinociceptive activity with less gastrointestinal side effects. Biochimie. 2015 Sep;116:24-33. doi: 10.1016/j.biochi.2015.06.008. Epub 2015 Jun 24. PubMed PMID: 26115815.

2: Zhang RS, Xu HJ, Jiang JH, Han RW, Chang M, Peng YL, Wang Y, Wang R. Endomorphin-1 attenuates Aβ42 induced impairment of novel object and object location recognition tasks in mice. Brain Res. 2015 Dec 10;1629:210-20. doi: 10.1016/j.brainres.2015.10.028. Epub 2015 Oct 23. PubMed PMID: 26505914.

3: Makuch W, Mika J, Rojewska E, Zychowska M, Przewlocka B. Effects of selective and non-selective inhibitors of nitric oxide synthase on morphine- and endomorphin-1-induced analgesia in acute and neuropathic pain in rats. Neuropharmacology. 2013 Dec;75:445-57. doi: 10.1016/j.neuropharm.2013.08.031. Epub 2013 Sep 10. PubMed PMID: 24035921.

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: Lengyel I, Toth F, Biyashev D, Szatmari I, Monory K, Tomboly C, Toth G, Benyhe S, Borsodi A. A novel non-opioid binding site for endomorphin-1. J Physiol Pharmacol. 2016 Aug;67(4):605-616. PubMed PMID: 27779481.

6: 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.

7: 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.

8: Duan L, Wang J, Sun X, Yang X, Shan L, Liu Y, Wang H. The role and significance of endomorphin-1 and μ-opioid receptor in rats with endometriosis. Gynecol Endocrinol. 2016 Nov;32(11):912-915. Epub 2016 Jun 2. PubMed PMID: 27252115.

9: Wang Y, Liu X, Wang D, Yang J, Zhao L, Yu J, Wang R. Endomorphin-1 analogues (MELs) penetrate the blood-brain barrier and exhibit good analgesic effects with minimal side effects. Neuropharmacology. 2015 Oct;97:312-21. doi: 10.1016/j.neuropharm.2015.06.010. Epub 2015 Jun 24. PubMed PMID: 26116761.

10: Eskandari S, Varamini P, Toth I. Formulation, characterization and permeability study of nano particles of lipo-endomorphin-1 for oral delivery. J Liposome Res. 2013 Dec;23(4):311-7. doi: 10.3109/08982104.2013.805339. Epub 2013 Aug 12. PubMed PMID: 23931529.

11: Wang CL, Zhou Y, Guo C, Zhang Y, Wang R. In vivo characterization of intestinal effects of endomorphin-1 and endomorphin-2 in type 1 diabetic mice. Eur J Pharmacol. 2013 Jan 5;698(1-3):499-504. doi: 10.1016/j.ejphar.2012.10.044. Epub 2012 Nov 6. PubMed PMID: 23142372.

12: Cros CD, Toth I, Blanchfield JT. Delivery of a lactose derivative of endomorphin 1 to the brain via the olfactory epithelial pathway. Bioorg Med Chem Lett. 2014 Mar 1;24(5):1373-5. doi: 10.1016/j.bmcl.2014.01.041. Epub 2014 Jan 26. PubMed PMID: 24508131.

13: Parra-Gámez L, García-Hidalgo A, Paredes RG. Infusion of endomorphin-1 (EM-1) in the MPOA and the Me modulate sexual and socio-sexual behavior in the male rat. Brain Res. 2013 Jun 23;1517:36-43. doi: 10.1016/j.brainres.2013.04.004. Epub 2013 Apr 13. PubMed PMID: 23587935.

14: Liu H, Zhang W, Ma L, Fan L, Gao F, Ni J, Wang R. The improved blood-brain barrier permeability of endomorphin-1 using the cell-penetrating peptide synB3 with three different linkages. Int J Pharm. 2014 Dec 10;476(1-2):1-8. doi: 10.1016/j.ijpharm.2014.08.045. Epub 2014 Sep 22. PubMed PMID: 25245547.

15: Varamini P, Goh WH, Mansfeld FM, Blanchfield JT, Wyse BD, Smith MT, Toth I. Peripherally acting novel lipo-endomorphin-1 peptides in neuropathic pain without producing constipation. Bioorg Med Chem. 2013 Apr 1;21(7):1898-904. doi: 10.1016/j.bmc.2013.01.044. Epub 2013 Jan 31. PubMed PMID: 23433669.

16: Chen T, Li J, Feng B, Hui R, Dong YL, Huo FQ, Zhang T, Yin JB, Du JQ, Li YQ. Mechanism Underlying the Analgesic Effect Exerted by Endomorphin-1 in the rat Ventrolateral Periaqueductal Gray. Mol Neurobiol. 2016 Apr;53(3):2036-2053. doi: 10.1007/s12035-015-9159-5. Epub 2015 Apr 16. PubMed PMID: 25876512.

17: Hung KC, Wu HE, Mizoguchi H, Tseng LF. Acute antinociceptive tolerance and unidirectional cross-tolerance to endomorphin-1 and endomorphin-2 given intraventricularly in the rat. Eur J Pharmacol. 2002 Jul 19;448(2-3):169-74. PubMed PMID: 12144938.

18: Zhang WP, Zong QF, Gao Q, Yu Y, Gu XY, Wang Y, Li ZH, Ge M. Effects of endomorphin-1 postconditioning on myocardial ischemia/reperfusion injury and myocardial cell apoptosis in a rat model. Mol Med Rep. 2016 Oct;14(4):3992-8. doi: 10.3892/mmr.2016.5695. Epub 2016 Aug 31. PubMed PMID: 27600942.

19: Liu X, Wang Y, Xing Y, Yu J, Ji H, Kai M, Wang Z, Wang D, Zhang Y, Zhao D, Wang R. Design, synthesis, and pharmacological characterization of novel endomorphin-1 analogues as extremely potent μ-opioid agonists. J Med Chem. 2013 Apr 11;56(7):3102-14. doi: 10.1021/jm400195y. Epub 2013 Mar 28. PubMed PMID: 23477419.

20: Varamini P, Mansfeld FM, Blanchfield JT, Wyse BD, Smith MT, Toth I. Lipo-endomorphin-1 derivatives with systemic activity against neuropathic pain without producing constipation. PLoS One. 2012;7(8):e41909. doi: 10.1371/journal.pone.0041909. Epub 2012 Aug 17. PubMed PMID: 22912681; PubMed Central PMCID: PMC3422351.