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MedKoo Cat#: 596831 | Name: Deltorphin

Description:

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

Deltorphin is Isolated from skin of Phyllomedusa sauvagei; has affinity to opioid receptor; note deltorphin I and deltorphin II are available, they have Ala in position 2.

Chemical Structure

Deltorphin
Deltorphin
CAS#119975-64-3

Theoretical Analysis

MedKoo Cat#: 596831

Name: Deltorphin

CAS#: 119975-64-3

Chemical Formula: C44H62N10O10S2

Exact Mass: 954.4092

Molecular Weight: 955.16

Elemental Analysis: C, 55.33; H, 6.54; N, 14.66; O, 16.75; S, 6.71

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.
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Related CAS #
No Data
Synonym
Deltorphin; Dermenkephalin; Deltorphin A;
IUPAC/Chemical Name
(5R,8S,11S,14S,17S,20S)-11-((1H-imidazol-4-yl)methyl)-5-((S)-2-amino-3-(4-hydroxyphenyl)propanamido)-8-benzyl-20-carbamoyl-14-isobutyl-17-(2-(methylthio)ethyl)-6,9,12,15,18-pentaoxo-2-thia-7,10,13,16,19-pentaazadocosan-22-oic acid
InChi Key
BHSURCCZOBVHJJ-NWOHMYAQSA-N
InChi Code
InChI=1S/C44H62N10O10S2/c1-25(2)18-34(42(62)50-32(15-17-66-4)40(60)51-33(38(46)58)22-37(56)57)52-44(64)36(21-28-23-47-24-48-28)54-43(63)35(20-26-8-6-5-7-9-26)53-41(61)31(14-16-65-3)49-39(59)30(45)19-27-10-12-29(55)13-11-27/h5-13,23-25,30-36,55H,14-22,45H2,1-4H3,(H2,46,58)(H,47,48)(H,49,59)(H,50,62)(H,51,60)(H,52,64)(H,53,61)(H,54,63)(H,56,57)/t30-,31+,32-,33-,34-,35-,36-/m0/s1
SMILES Code
O=C(O)C[C@@H](C(N)=O)NC([C@H](CCSC)NC([C@H](CC(C)C)NC([C@H](CC1=CNC=N1)NC([C@H](CC2=CC=CC=C2)NC([C@@H](CCSC)NC([C@H](CC3=CC=C(O)C=C3)N)=O)=O)=O)=O)=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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 955.16 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
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PubMed PMID: 28864212. 4: Margolis EB, Fujita W, Devi LA, Fields HL. Two delta opioid receptor subtypes are functional in single ventral tegmental area neurons, and can interact with the mu opioid receptor. Neuropharmacology. 2017 Sep 1;123:420-432. doi: 10.1016/j.neuropharm.2017.06.019. Epub 2017 Jun 21. PubMed PMID: 28645621; PubMed Central PMCID: PMC5563499. 5: Zádor F, Király K, Váradi A, Balogh M, Fehér Á, Kocsis D, Erdei AI, Lackó E, Zádori ZS, Hosztafi S, Noszál B, Riba P, Benyhe S, Fürst S, Al-Khrasani M. New opioid receptor antagonist: Naltrexone-14-O-sulfate synthesis and pharmacology. Eur J Pharmacol. 2017 Aug 15;809:111-121. doi: 10.1016/j.ejphar.2017.05.024. Epub 2017 May 11. PubMed PMID: 28502630. 6: Seewald M, Coles JA Jr, Sigg DC, Iaizzo PA. Featured Article: Pharmacological postconditioning with delta opioid attenuates myocardial reperfusion injury in isolated porcine hearts. Exp Biol Med (Maywood). 2017 May;242(9):986-995. doi: 10.1177/1535370216684041. Epub 2016 Jan 1. PubMed PMID: 28440739; PubMed Central PMCID: PMC5407584. 7: Mukhomedzyanov AV, Maslov LN, Ovchinnikov MV, Sidorova MV, Pei JM, Tsibul'nikov SY, Tsepokina AV, Khutornaya MV, Kutikhin AG. Effects of Deltorphin II and Its Retroenantio Analog on Cardiac Tolerance to Ischemia and Reperfusion. Bull Exp Biol Med. 2017 Jan;162(3):306-309. doi: 10.1007/s10517-017-3601-9. Epub 2017 Jan 14. PubMed PMID: 28091919. 8: Nadon JF, Rochon K, Grastilleur S, Langlois G, Dao TT, Blais V, Guérin B, Gendron L, Dory YL. Synthesis of Gly-ψ[(Z)CF═CH]-Phe, a Fluoroalkene Dipeptide Isostere, and Its Incorporation into a Leu-enkephalin Peptidomimetic. ACS Chem Neurosci. 2017 Jan 18;8(1):40-49. doi: 10.1021/acschemneuro.6b00163. Epub 2016 Nov 3. PubMed PMID: 27762555. 9: Liu FY, Zhang MM, Zeng P, Liu WW, Wang JL, Yang B, Dai Q, Wei J. Study on the molecular mechanism of antinociception induced by ghrelin in acute pain in mice. Peptides. 2016 Sep;83:1-7. doi: 10.1016/j.peptides.2016.07.006. Epub 2016 Jul 26. PubMed PMID: 27474249. 10: Kiguchi Y, Aono Y, Watanabe Y, Yamamoto-Nemoto S, Shimizu K, Shimizu T, Kosuge Y, Waddington JL, Ishige K, Ito Y, Saigusa T. In vivo neurochemical evidence that delta1-, delta2- and mu2-opioid receptors, but not mu1-opioid receptors, inhibit acetylcholine efflux in the nucleus accumbens of freely moving rats. Eur J Pharmacol. 2016 Oct 15;789:402-410. doi: 10.1016/j.ejphar.2016.07.028. Epub 2016 Jul 18. PubMed PMID: 27445235. 11: Lasota A, Frączak O, Muchowska A, Nowakowski M, Maciejczyk M, Ejchart A, Olma A. Synthesis, Biological Activity, and NMR-Based Structural Studies of Deltorphin I Analogs Modified in Message Domain with a New α,α-Disubstituted Glycines. Chem Biol Drug Des. 2016 Jun;87(6):824-32. doi: 10.1111/cbdd.12730. Epub 2016 Feb 20. PubMed PMID: 26808639. 12: Gein SV, Tendryakova SP. [Agonists of µ- and δ-Opioid Receptors in the Regulation of IL-2, IL-4 and IFN-γ Production by Peripheral Blood Cells in vitro]. Fiziol Cheloveka. 2015 May-Jun;41(3):112-7. Russian. PubMed PMID: 26237955. 13: Vardy E, Sassano MF, Rennekamp AJ, Kroeze WK, Mosier PD, Westkaemper RB, Stevens CW, Katritch V, Stevens RC, Peterson RT, Roth BL. Single Amino Acid Variation Underlies Species-Specific Sensitivity to Amphibian Skin-Derived Opioid-like Peptides. Chem Biol. 2015 Jun 18;22(6):764-75. doi: 10.1016/j.chembiol.2015.05.012. PubMed PMID: 26091169; PubMed Central PMCID: PMC4507497. 14: Brederson JD, Honda CN. Primary afferent neurons express functional delta opioid receptors in inflamed skin. Brain Res. 2015 Jul 21;1614:105-11. doi: 10.1016/j.brainres.2015.04.023. Epub 2015 Apr 22. PubMed PMID: 25911583; PubMed Central PMCID: PMC4457631. 15: Pescatore R, Marrone GF, Sedberry S, Vinton D, Finkelstein N, Katlowitz YE, Pasternak GW, Wilson KR, Majumdar S. Synthesis and pharmacology of halogenated δ-opioid-selective [d-Ala(2)]deltorphin II peptide analogues. ACS Chem Neurosci. 2015 Jun 17;6(6):905-10. doi: 10.1021/acschemneuro.5b00060. Epub 2015 Apr 14. PubMed PMID: 25844930; PubMed Central PMCID: PMC4472604. 16: Kozyrev N, Coolen LM. Activation of mu or delta opioid receptors in the lumbosacral spinal cord is essential for ejaculatory reflexes in male rats. PLoS One. 2015 Mar 31;10(3):e0121130. doi: 10.1371/journal.pone.0121130. eCollection 2015. PubMed PMID: 25826331; PubMed Central PMCID: PMC4380469. 17: Bańkowski K, Michalak OM, Leśniak A, Filip KE, Cmoch P, Szewczuk Z, Stefanowicz P, Izdebski J. N-terminal guanidinylation of the cyclic 1,4-ureido-deltorphin analogues: the synthesis, receptor binding studies, and resistance to proteolytic digestion. J Pept Sci. 2015 Jun;21(6):467-75. doi: 10.1002/psc.2762. Epub 2015 Mar 4. PubMed PMID: 25755050. 18: Beaudry H, Mercier-Blais AA, Delaygue C, Lavoie C, Parent JL, Neugebauer W, Gendron L. Regulation of μ and δ opioid receptor functions: involvement of cyclin-dependent kinase 5. Br J Pharmacol. 2015 May;172(10):2573-87. doi: 10.1111/bph.13088. Epub 2015 Mar 24. PubMed PMID: 25598508; PubMed Central PMCID: PMC4409908. 19: Lasota A, Frączak O, Leśniak A, Muchowska A, Lipkowski AW, Nowakowski M, Ejchart A, Olma A. Analogues of deltorphin I containing conformationally restricted amino acids in position 2: structure and opioid activity. J Pept Sci. 2015 Feb;21(2):120-5. doi: 10.1002/psc.2738. Epub 2014 Dec 30. PubMed PMID: 25558014. 20: Wang C, Li Y, Wang H, Xie K, Shu R, Zhang L, Hu N, Yu Y, Wang G. Inhibition of DOR prevents remifentanil induced postoperative hyperalgesia through regulating the trafficking and function of spinal NMDA receptors in vivo and in vitro. Brain Res Bull. 2015 Jan;110:30-9. doi: 10.1016/j.brainresbull.2014.12.001. Epub 2014 Dec 9. PubMed PMID: 25498394.

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