Morphiceptin | CAS#74135-04-9 | synthetic tetrapeptide

MedKoo Cat#: 597818 | Name: Morphiceptin

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Description:

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

Morphiceptin is a synthetic tetrapeptide with morphinelike activities, highly specific for morphine receptors, but not for enkephalin receptors; is the amide of a fragment of the milk protein beta casein; deproceptin is the D-Pro(4)-isomer.

Chemical Structure

Morphiceptin

CAS#74135-04-9

Theoretical Analysis

MedKoo Cat#: 597818

Name: Morphiceptin

CAS#: 74135-04-9

Chemical Formula: C28H35N5O5

Exact Mass: 521.2638

Molecular Weight: 521.62

Elemental Analysis: C, 64.47; H, 6.76; N, 13.43; O, 15.34

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 370.00	2 Weeks
25mg	USD 635.00	2 Weeks

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Related CAS #

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Synonym

Morphiceptin; Deproceptin; Tyr-pro-phe-pro amide;

IUPAC/Chemical Name

(S)-1-(L-tyrosyl)-N-((S)-1-((S)-2-carbamoylpyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)pyrrolidine-2-carboxamide

InChi Key

LSQXZIUREIDSHZ-ZJZGAYNASA-N

InChi Code

InChI=1S/C28H35N5O5/c29-21(16-19-10-12-20(34)13-11-19)27(37)33-15-5-9-24(33)26(36)31-22(17-18-6-2-1-3-7-18)28(38)32-14-4-8-23(32)25(30)35/h1-3,6-7,10-13,21-24,34H,4-5,8-9,14-17,29H2,(H2,30,35)(H,31,36)/t21-,22-,23-,24-/m0/s1

SMILES Code

O=C(N)[C@H]1N(C([C@H](CC2=CC=CC=C2)NC([C@H]3N(C([C@H](CC4=CC=C(O)C=C4)N)=O)CCC3)=O)=O)CCC1

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Morphiceptin is a potent and specific agonist for morphine (μ) receptors.

In vitro activity:

TBD

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	125.0	239.64
	Water	250.0	479.28

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 521.62 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

Formulation protocol:

TBD

In vitro protocol:

TBD

In vivo protocol:

TBD

1: Adamska A, Kluczyk A, Cerlesi MC, Calo G, Janecka A, Borics A. Synthesis, biological evaluation and structural analysis of novel peripherally active morphiceptin analogs. Bioorg Med Chem. 2016 Apr 1;24(7):1582-8. doi: 10.1016/j.bmc.2016.02.034. Epub 2016 Feb 26. PubMed PMID: 26944625. 2: Li M, Zhou L, Ma G, Dong S. Analgesic properties of chimeric peptide based on morphiceptin and PFRTic-amide. Regul Pept. 2012 Nov 10;179(1-3):23-8. doi: 10.1016/j.regpep.2012.08.008. Epub 2012 Sep 4. PubMed PMID: 22960407. 3: Gach K, do-Rego JC, Fichna J, Storr M, Delbro D, Toth G, Janecka A. Synthesis and biological evaluation of novel peripherally active morphiceptin analogs. Peptides. 2010 Aug;31(8):1617-24. doi: 10.1016/j.peptides.2010.04.018. Epub 2010 Apr 29. PubMed PMID: 20434497. 4: Zhang J, He C, Pi X, Wang Y, Zhou L, Dong S. MCRT, a chimeric peptide based on morphiceptin and PFRTic-NH(2), regulates the depressor effects induced by endokinin A/B. Eur J Pharmacol. 2016 Dec 5;792:33-37. doi: 10.1016/j.ejphar.2016.10.028. Epub 2016 Oct 23. PubMed PMID: 27784644. 5: Zubrzycka M, Fichna J, Janecka A. Effect of cerebral ventricles perfusion with morphiceptin and Met-enkephalin on trigemino-hypoglossal reflex in rats. J Physiol Pharmacol. 2002 Dec;53(4 Pt 2):741-50. PubMed PMID: 12510860. 6: Matuszewich L, Ormsby JL, Moses J, Lorrain DS, Hull EM. Effects of morphiceptin in the medial preoptic area on male sexual behavior. Psychopharmacology (Berl). 1995 Dec;122(4):330-5. PubMed PMID: 8657829. 7: Fichna J, do-Rego JC, Kosson P, Costentin J, Janecka A. Characterization of antinociceptive activity of novel endomorphin-2 and morphiceptin analogs modified in the third position. Biochem Pharmacol. 2005 Jan 1;69(1):179-85. PubMed PMID: 15588726. 8: Li M, Zhou L, Ma G, Cao S, Dong S. The cardiovascular effects of a chimeric opioid peptide based on morphiceptin and PFRTic-NH2. Peptides. 2013 Jan;39:89-94. doi: 10.1016/j.peptides.2012.10.014. Epub 2012 Nov 14. PubMed PMID: 23159788. 9: Widy-Tyszkiewicz E, Członkowski A, Szreniawski Z. Cardiovascular responses to morphiceptin in spontaneously hypertensive and normotensive rats. Pol J Pharmacol Pharm. 1986 Jan-Feb;38(1):51-6. PubMed PMID: 3763486. 10: Fichna J, do-Rego JC, Costentin J, Chung NN, Schiller PW, Kosson P, Janecka A. Opioid receptor binding and in vivo antinociceptive activity of position 3-substituted morphiceptin analogs. Biochem Biophys Res Commun. 2004 Jul 23;320(2):531-6. PubMed PMID: 15219861. 11: Mahe S, Tome D, Dumontier AM, Desjeux JF. Absorption of intact morphiceptin by diisopropylfluorophosphate-treated rabbit ileum. Peptides. 1989 Jan-Feb;10(1):45-52. PubMed PMID: 2473450. 12: Pfaus JG, Pendleton N, Gorzalka BB. Dual effect of morphiceptin on lordosis behavior: possible mediation by different opioid receptor subtypes. Pharmacol Biochem Behav. 1986 May;24(5):1461-4. PubMed PMID: 3014568. 13: Fichna J, do-Rego JC, Chung NN, Costentin J, Schiller PW, Janecka A. [Dmt1, d-1-Nal3]morphiceptin, a novel opioid peptide analog with high analgesic activity. Peptides. 2008 Apr;29(4):633-8. doi: 10.1016/j.peptides.2007.12.005. Epub 2007 Dec 23. PubMed PMID: 18234394. 14: Janecka A, Fichna J, Mirowski M, Janecki T. Structure-activity relationship, conformation and pharmacology studies of morphiceptin analogues--selective mu-opioid receptor ligands. Mini Rev Med Chem. 2002 Dec;2(6):565-72. Review. PubMed PMID: 12370041. 15: Giordano C, Sansone A, Masi A, Lucente G, Punzi P, Mollica A, Pinnen F, Feliciani F, Cacciatore I, Davis P, Lai J, Ma SW, Porreca F, Hruby V. Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2. Eur J Med Chem. 2010 Oct;45(10):4594-600. doi: 10.1016/j.ejmech.2010.07.022. Epub 2010 Jul 21. PubMed PMID: 20692738; PubMed Central PMCID: PMC5689459. 16: Villiger JW. Morphiceptin: biphasic inhibition of mu-opiate receptor ligands. Pharmacol Biochem Behav. 1984 Nov;21(5):705-6. PubMed PMID: 6096895. 17: Zadina JE, Kastin AJ. Interactions between the antiopiate Tyr-MIF-1 and the mu opiate morphiceptin at their respective binding sites in brain. Peptides. 1985 Sep-Oct;6(5):965-70. PubMed PMID: 2867527. 18: Ota T, Itoh A, Tachi H, Kudoh K, Watanabe T, Yamamoto Y, Tadokoro T, Maekawa A. Synthesis of morphiceptin (Tyr-Pro-Phe-Pro-NH(2)) by dipeptidyl aminopeptidase IV derived from Aspergillus oryzae. J Agric Food Chem. 2005 Jul 27;53(15):6112-6. PubMed PMID: 16029004. 19: Janecka A, Fichna J, Kosson P, Zalewska-Kaszubska J, Krajewska U, Mirowski M, Rozalski M. Binding of the new morphiceptin analogs to human MCF-7 breast cancer cells and their effect on growth. Regul Pept. 2004 Aug 15;120(1-3):237-41. PubMed PMID: 15177942. 20: Shimohigashi Y, Sakaguchi K, Sakamoto H, Waki M, Costa T. Opioid activities of morphiceptin-like peptides latent in various natural proteins. Pept Res. 1990 Sep-Oct;3(5):216-23. PubMed PMID: 1966866.