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MedKoo Cat#: 461333 | Name: Rimorphin
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Description:

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

Rimorphin, also known as Dynorphin B-13 or Dynorphin B, is an opioid peptide derived from prodynorphin and a κ-opioid receptor.

Chemical Structure

Rimorphin
Rimorphin
CAS#83335-41-5

Theoretical Analysis

MedKoo Cat#: 461333

Name: Rimorphin

CAS#: 83335-41-5

Chemical Formula: C74H115N21O17

Exact Mass: 1569.8780

Molecular Weight: 1570.86

Elemental Analysis: C, 56.58; H, 7.38; N, 18.73; O, 17.31

Price and Availability

Size Price Availability Quantity
1mg USD 300.00
5mg USD 870.00
10mg USD 1,140.00
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Related CAS #
No Data
Synonym
Rimorphin; Dynorphin B;
IUPAC/Chemical Name
A name could not be generated for this structure.
InChi Key
AGTSSZRZBSNTGQ-BREXGJBKSA-N
InChi Code
InChI=1S/C74H115N21O17/c1-40(2)34-53(91-68(107)54(36-44-18-10-8-11-19-44)86-58(100)39-84-57(99)38-85-62(101)48(76)35-46-25-27-47(97)28-26-46)67(106)89-51(24-17-33-83-74(80)81)63(102)87-50(23-16-32-82-73(78)79)64(103)90-52(29-30-56(77)98)65(104)92-55(37-45-20-12-9-13-21-45)69(108)88-49(22-14-15-31-75)66(105)93-59(41(3)4)70(109)94-60(42(5)6)71(110)95-61(43(7)96)72(111)112/h8-13,18-21,25-28,40-43,48-55,59-61,96-97H,14-17,22-24,29-39,75-76H2,1-7H3,(H2,77,98)(H,84,99)(H,85,101)(H,86,100)(H,87,102)(H,88,108)(H,89,106)(H,90,103)(H,91,107)(H,92,104)(H,93,105)(H,94,109)(H,95,110)(H,111,112)(H4,78,79,82)(H4,80,81,83)/t43-,48-,49-,50-,51-,52+,53-,54-,55+,59+,60+,61+/m0/s1
SMILES Code
Oc1ccc(C[C@H](N)C(NCC(NCC(N[C@@H](Cc2ccccc2)C(N[C@@H](CC(C)C)C(N[C@H](C(N[C@@H](CCCNC(N)=N)C(N[C@@H](C(N[C@H](Cc3ccccc3)C(N[C@H](C(N[C@H](C(C)C)C(N[C@@H](C(N[C@@H](C(O)=O)[C@@H](O)C)=O)C(C)C)=O)=O)CCCCN)=O)=O)CCC(N)=O)=O)=O)CCCNC(N)=N)=O)=O)=O)=O)=O)cc1
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:
Rimorphin acts as a κ1b-opioid receptor agonist (Ki = 1.1 nM) and has been implicated in antinociceptive functions. Rimorphin has also been used to prime cardiogenesis in pluripotent embryonic stem cells.
In vitro activity:
Exposure of isolated embryonic stem cells nuclei to dynorphin B induced a significant increase in nuclear protein kinase C activity. Nuclear treatment with protein kinase C inhibitors abolished the capability of dynorphin B to prime the transcription of cardiogenic genes. Reference: Circ Res. 2003 Apr 4;92(6):623-9. https://pubmed.ncbi.nlm.nih.gov/12623878/
In vivo activity:
Intracerebrally administered dynorphin-B produced an antinociceptive response and motor dysfunction. Results of this study suggest that dynorphin-B produced an analgesia through opioid receptors and that this peptide also induced a motor dysfunction through a nonopioid receptor. Reference: Neuropeptides. 1989 May-Jun;13(4):277-83. https://pubmed.ncbi.nlm.nih.gov/2568600/
Solvent mg/mL mM
Solubility
DMSO 30.0 19.10
DMF 30.0 19.10
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 1,570.86 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:
1. Ventura C, Zinellu E, Maninchedda E, Maioli M. Dynorphin B is an agonist of nuclear opioid receptors coupling nuclear protein kinase C activation to the transcription of cardiogenic genes in GTR1 embryonic stem cells. Circ Res. 2003 Apr 4;92(6):623-9. doi: 10.1161/01.RES.0000065169.23780.0E. Epub 2003 Mar 6. PMID: 12623878. 2. Joshi AA, Murray TF, Aldrich JV. Alanine scan of the opioid peptide dynorphin B amide. Biopolymers. 2017 Sep;108(5):10.1002/bip.23026. doi: 10.1002/bip.23026. PMID: 28464209; PMCID: PMC6003702. 3. Pugh G Jr, Mason DJ Jr, Combs V, Welch SP. Involvement of dynorphin B in the antinociceptive effects of the cannabinoid CP55,940 in the spinal cord. J Pharmacol Exp Ther. 1997 May;281(2):730-7. PMID: 9152379. 4. Nakazawa T, Ikeda M, Kaneko T, Yamatsu K, Kitagawa K, Kiso Y. Bestatin potentiates the antinociception but not the motor dysfunction induced by intracerebrally administered dynorphin-B in mice. Neuropeptides. 1989 May-Jun;13(4):277-83. doi: 10.1016/0143-4179(89)90082-6. PMID: 2568600.
In vitro protocol:
1. Ventura C, Zinellu E, Maninchedda E, Maioli M. Dynorphin B is an agonist of nuclear opioid receptors coupling nuclear protein kinase C activation to the transcription of cardiogenic genes in GTR1 embryonic stem cells. Circ Res. 2003 Apr 4;92(6):623-9. doi: 10.1161/01.RES.0000065169.23780.0E. Epub 2003 Mar 6. PMID: 12623878. 2. Joshi AA, Murray TF, Aldrich JV. Alanine scan of the opioid peptide dynorphin B amide. Biopolymers. 2017 Sep;108(5):10.1002/bip.23026. doi: 10.1002/bip.23026. PMID: 28464209; PMCID: PMC6003702.
In vivo protocol:
1. Pugh G Jr, Mason DJ Jr, Combs V, Welch SP. Involvement of dynorphin B in the antinociceptive effects of the cannabinoid CP55,940 in the spinal cord. J Pharmacol Exp Ther. 1997 May;281(2):730-7. PMID: 9152379. 2. Nakazawa T, Ikeda M, Kaneko T, Yamatsu K, Kitagawa K, Kiso Y. Bestatin potentiates the antinociception but not the motor dysfunction induced by intracerebrally administered dynorphin-B in mice. Neuropeptides. 1989 May-Jun;13(4):277-83. doi: 10.1016/0143-4179(89)90082-6. PMID: 2568600.
1: Nakao K, Yoshimasa T, Suda M, Sakamoto M, Ikeda Y, Hayashi K, Imura H. Rimorphin (dynorphin B) exists together with alpha-neo-endorphin and dynorphin (dynorphin A) in human hypothalamus. Biochem Biophys Res Commun. 1983 May 31;113(1):30-4. doi: 10.1016/0006-291x(83)90427-8. PMID: 6134527. 2: Matsumoto RR, Lohof AM, Patrick RL, Walker JM. Dopamine-independent motor behavior following microinjection of rimorphin in the substantia nigra. Brain Res. 1988 Mar 15;444(1):67-74. doi: 10.1016/0006-8993(88)90914-6. PMID: 2896062. 3: Herman TF, Cascella M, Muzio MR. Mu Receptors. 2024 Jun 8. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2024 Jan–. PMID: 31855381. 4: Kilpatrick DL, Wahlstrom A, Lahm HW, Blacher R, Udenfriend S. Rimorphin, a unique, naturally occurring [Leu]enkephalin-containing peptide found in association with dynorphin and alpha-neo-endorphin. Proc Natl Acad Sci U S A. 1982 Nov;79(21):6480-3. doi: 10.1073/pnas.79.21.6480. PMID: 6128731; PMCID: PMC347150. 5: Kiso Y, Inai M, Kitagawa K, Akita T, Moritoki H. Synthesis of a newly isolated opioid tridecapeptide, rimorphin, from pituitary using a trifluoroacetic acid-thioanisole deprotection system. Chem Pharm Bull (Tokyo). 1983 May;31(5):1818-20. doi: 10.1248/cpb.31.1818. PMID: 6616729. 6: Suda M, Nakao K, Yoshimasa T, Ikeda Y, Sakamoto M, Yanaihara C, Yanaihara N, Numa S, Imura H. Comparison of the action of putative endogenous kappa-agonists, leumorphin and rimorphin in vitro. Life Sci. 1983;33 Suppl 1:275-8. doi: 10.1016/0024-3205(83)90496-4. PMID: 6319876. 7: Ishizuka J, Toyota T, Ono T, Sasaki M, Yanaihara C, Yanaihara N. Inhibitory effects of rimorphin and dynorphin on insulin secretion from the isolated, perfused rat pancreas. Tohoku J Exp Med. 1986 Sep;150(1):17-24. doi: 10.1620/tjem.150.17. PMID: 2877510. 8: Quirion R. Pain, nociception and spinal opioid receptors. Prog Neuropsychopharmacol Biol Psychiatry. 1984;8(4-6):571-9. doi: 10.1016/0278-5846(84)90017-4. PMID: 6152341. 9: Wolter HJ. Identification of the tridecapeptide dynorphin B (rimorphin) within perikarya of rat duodenum. Life Sci. 1986 Aug 25;39(8):727-30. doi: 10.1016/0024-3205(86)90020-2. PMID: 2874472. 10: Cheido MA, Idova GV. The contribution of serotonin 1A receptors to kappa opioid immunosuppression. Neurosci Behav Physiol. 2009 Jul;39(6):587-90. doi: 10.1007/s11055-009-9169-8. Epub 2009 Jun 11. PMID: 19517245. 11: Jacobs JW, Fodor SP. Combinatorial chemistry--applications of light-directed chemical synthesis. Trends Biotechnol. 1994 Jan;12(1):19-26. doi: 10.1016/0167-7799(94)90007-8. PMID: 7765338. 12: Zhu YX, Höllt V, Loh H. Immunoreactive peptides related to dynorphin B (= rimorphin) in the rat brain. Peptides. 1983 Nov-Dec;4(6):871-4. doi: 10.1016/0196-9781(83)90083-9. PMID: 6143300. 13: Kilpatrick DL, Wahlström A, Lahm HW, Blacher R, Ezra E, Fleminger G, Udenfriend S. Characterization of rimorphin, a new [leu]enkephalin-containing peptide from bovine posterior pituitary glands. Life Sci. 1982 Oct 18-25;31(16-17):1849-52. doi: 10.1016/0024-3205(82)90226-0. PMID: 7154838. 14: Akhmedov NA, Makhmudova TA, Khalilov RI, Zeĭnalova NM. Strukturnaia organizatsiia rimorfina i ego sinteticheskikh analogov [Structural organization of rimorphin and its synthetic analogs]. Bioorg Khim. 1995 Aug;21(8):587-9. Russian. PMID: 8540899. 15: Lind J, Gräslund A, Mäler L. Membrane interactions of dynorphins. Biochemistry. 2006 Dec 26;45(51):15931-40. doi: 10.1021/bi061199g. Epub 2006 Dec 1. PMID: 17176116. 16: Hugonin L, Vukojević V, Bakalkin G, Gräslund A. Membrane leakage induced by dynorphins. FEBS Lett. 2006 May 29;580(13):3201-5. doi: 10.1016/j.febslet.2006.04.078. Epub 2006 May 4. PMID: 16697372. 17: Wei H, Dean SL, Parkin MC, Nolkrantz K, O'Callaghan JP, Kennedy RT. Microscale sample deposition onto hydrophobic target plates for trace level detection of neuropeptides in brain tissue by MALDI-MS. J Mass Spectrom. 2005 Oct;40(10):1338-46. doi: 10.1002/jms.916. PMID: 16217843. 18: Kilpatrick DL, Eisen M, Ezra E, Udenfriend S. Processing of prodynorphin at single and paired basic residues in porcine neurointermediate lobe. Life Sci. 1983;33 Suppl 1:93-6. doi: 10.1016/0024-3205(83)90452-6. PMID: 6689356. 19: Yakovleva T, Marinova Z, Kuzmin A, Seidah NG, Haroutunian V, Terenius L, Bakalkin G. Dysregulation of dynorphins in Alzheimer disease. Neurobiol Aging. 2007 Nov;28(11):1700-8. doi: 10.1016/j.neurobiolaging.2006.07.002. Epub 2006 Aug 17. PMID: 16914231. 20: Devi L. Tissue distribution of a dynorphin-processing endopeptidase. Endocrinology. 1993 Mar;132(3):1139-44. doi: 10.1210/endo.132.3.8095013. PMID: 8095013.