Herkinorin
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MedKoo CAT#: 584172

CAS#: 862073-77-6

Description: Herkinorin is an opioid analgesic that is an analogue of the natural product Salvinorin A. Unlike Salvinorin A which is a selective κ-opioid agonist with no significant μ-opioid receptor affinity, herkinorin is a μ-opioid agonist with more than 100x higher μ-opioid affinity and 50x lower κ-opioid affinity compared to Salvinorin A. Herkinorin is a semi-synthetic compound, made from Salvinorin B, which is most conveniently made from Salvinorin A by deacetylation, as while both Salvinorin A and Salvinorin B are found in the plant Salvia divinorum, Salvinorin A is present in larger quantities.

Chemical Structure

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Herkinorin
CAS# 862073-77-6
Instruction

Theoretical Analysis

MedKoo Cat#: 584172
Name: Herkinorin
CAS#: 862073-77-6
Chemical Formula: C28H30O8
Exact Mass: 494.19
Molecular Weight: 494.540
Elemental Analysis: C, 68.00; H, 6.11; O, 25.88

Price and Availability

Size Price Availability Quantity
1mg USD 435 2 Weeks
5mg USD 1250 2 Weeks
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Synonym: BF3DNCA methyl ester; Herkinorin.

IUPAC/Chemical Name: 9-(benzoyloxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho(2,1-c)pyran-7-carboxylic acid methyl ester

InChi Key: PYDQMXRFUVDCHC-UHFFFAOYSA-N

InChi Code: InChI=1S/C28H30O8/c1-27-11-9-18-26(32)36-21(17-10-12-34-15-17)14-28(18,2)23(27)22(29)20(13-19(27)25(31)33-3)35-24(30)16-7-5-4-6-8-16/h4-8,10,12,15,18-21,23H,9,11,13-14H2,1-3H3

SMILES Code: O=C(C(CC(OC(C1=CC=CC=C1)=O)C(C23)=O)C2(C)CCC(C3(C)CC(C4=COC=C4)O5)C5=O)OC

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 494.54 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: Butelman ER, Rus S, Simpson DS, Wolf A, Prisinzano TE, Kreek MJ. The effects of herkinorin, the first mu-selective ligand from a salvinorin A-derived scaffold, in a neuroendocrine biomarker assay in nonhuman primates. J Pharmacol Exp Ther. 2008 Oct;327(1):154-60. doi: 10.1124/jpet.108.140079. Epub 2008 Jul 1. PubMed PMID: 18593955; PubMed Central PMCID: PMC2614932.

2: Ji F, Wang Z, Ma N, Riley J, Armstead WM, Liu R. Herkinorin dilates cerebral vessels via kappa opioid receptor and cyclic adenosine monophosphate (cAMP) in a piglet model. Brain Res. 2013 Jan 15;1490:95-100. doi: 10.1016/j.brainres.2012.10.024. Epub 2012 Oct 24. PubMed PMID: 23103502; PubMed Central PMCID: PMC3529796.

3: Lamb K, Tidgewell K, Simpson DS, Bohn LM, Prisinzano TE. Antinociceptive effects of herkinorin, a MOP receptor agonist derived from salvinorin A in the formalin test in rats: new concepts in mu opioid receptor pharmacology: from a symposium on new concepts in mu-opioid pharmacology. Drug Alcohol Depend. 2012 Mar 1;121(3):181-8. doi: 10.1016/j.drugalcdep.2011.10.026. Epub 2011 Nov 26. PubMed PMID: 22119134; PubMed Central PMCID: PMC3288203.

4: Xu H, Partilla JS, Wang X, Rutherford JM, Tidgewell K, Prisinzano TE, Bohn LM, Rothman RB. A comparison of noninternalizing (herkinorin) and internalizing (DAMGO) mu-opioid agonists on cellular markers related to opioid tolerance and dependence. Synapse. 2007 Mar;61(3):166-75. PubMed PMID: 17152090.

5: Rowan MP, Bierbower SM, Eskander MA, Szteyn K, Por ED, Gomez R, Veldhuis N, Bunnett NW, Jeske NA. Activation of mu opioid receptors sensitizes transient receptor potential vanilloid type 1 (TRPV1) via β-arrestin-2-mediated cross-talk. PLoS One. 2014 Apr 2;9(4):e93688. doi: 10.1371/journal.pone.0093688. eCollection 2014. PubMed PMID: 24695785; PubMed Central PMCID: PMC3973553.

6: Tidgewell K, Groer CE, Harding WW, Lozama A, Schmidt M, Marquam A, Hiemstra J, Partilla JS, Dersch CM, Rothman RB, Bohn LM, Prisinzano TE. Herkinorin analogues with differential beta-arrestin-2 interactions. J Med Chem. 2008 Apr 24;51(8):2421-31. doi: 10.1021/jm701162g. Epub 2008 Apr 2. PubMed PMID: 18380425; PubMed Central PMCID: PMC2494883.

7: Bartuzi D, Kaczor AA, Matosiuk D. Activation and Allosteric Modulation of Human μ Opioid Receptor in Molecular Dynamics. J Chem Inf Model. 2015 Nov 23;55(11):2421-34. doi: 10.1021/acs.jcim.5b00280. Epub 2015 Nov 11. PubMed PMID: 26517559.

8: Prisinzano TE. Neoclerodanes as atypical opioid receptor ligands. J Med Chem. 2013 May 9;56(9):3435-43. doi: 10.1021/jm400388u. Epub 2013 Apr 18. Review. PubMed PMID: 23548164; PubMed Central PMCID: PMC3671615.

9: Sally EJ, Xu H, Dersch CM, Hsin LW, Chang LT, Prisinzano TE, Simpson DS, Giuvelis D, Rice KC, Jacobson AE, Cheng K, Bilsky EJ, Rothman RB. Identification of a novel "almost neutral" micro-opioid receptor antagonist in CHO cells expressing the cloned human mu-opioid receptor. Synapse. 2010 Apr;64(4):280-8. doi: 10.1002/syn.20723. PubMed PMID: 19953652; PubMed Central PMCID: PMC2821452.

10: Marmolejo-Valencia AF, Martínez-Mayorga K. Allosteric modulation model of the mu opioid receptor by herkinorin, a potent not alkaloidal agonist. J Comput Aided Mol Des. 2017 May;31(5):467-482. doi: 10.1007/s10822-017-0016-7. Epub 2017 Mar 31. PubMed PMID: 28364251.

11: Holden KG, Tidgewell K, Marquam A, Rothman RB, Navarro H, Prisinzano TE. Synthetic studies of neoclerodane diterpenes from Salvia divinorum: exploration of the 1-position. Bioorg Med Chem Lett. 2007 Nov 15;17(22):6111-5. Epub 2007 Sep 15. PubMed PMID: 17904842; PubMed Central PMCID: PMC2111044.

12: Someya E, Mori A, Sakamoto K, Ishii K, Nakahara T. Stimulation of μ-opioid receptors dilates retinal arterioles by neuronal nitric oxide synthase-derived nitric oxide in rats. Eur J Pharmacol. 2017 May 15;803:124-129. doi: 10.1016/j.ejphar.2017.03.043. Epub 2017 Mar 22. PubMed PMID: 28341346.

13: Gui X, Cui X, Wei H, Feng G, Zhang X, He Y, Li J, Li T. cPKCγ membrane translocation is involved in herkinorin induced neuroprotection against cerebral ischemia/reperfusion injury in mice. Mol Med Rep. 2017 Jan;15(1):221-227. doi: 10.3892/mmr.2016.5995. Epub 2016 Dec 6. PubMed PMID: 27922694; PubMed Central PMCID: PMC5355757.

14: Martin DJ, FitzMorris PE, Li B, Ayestas M, Sally EJ, Dersch CM, Rothman RB, Deveau AM. An efficient synthesis of 3-OBn-6β,14-epoxy-bridged opiates from naltrexone and identification of a related dual MOR inverse agonist/KOR agonist. Bioorg Med Chem Lett. 2012 Nov 15;22(22):6801-5. doi: 10.1016/j.bmcl.2012.06.056. Epub 2012 Jun 23. PubMed PMID: 22771010.

15: Xu H, Wang X, Partilla JS, Bishop-Mathis K, Benaderet TS, Dersch CM, Simpson DS, Prisinzano TE, Rothman RB. Differential effects of opioid agonists on G protein expression in CHO cells expressing cloned human opioid receptors. Brain Res Bull. 2008 Sep 5;77(1):49-54. doi: 10.1016/j.brainresbull.2008.05.003. Epub 2008 Jun 4. PubMed PMID: 18639745; PubMed Central PMCID: PMC2538684.

16: Shim J, Coop A, MacKerell AD Jr. Consensus 3D model of μ-opioid receptor ligand efficacy based on a quantitative Conformationally Sampled Pharmacophore. J Phys Chem B. 2011 Jun 9;115(22):7487-96. doi: 10.1021/jp202542g. Epub 2011 May 12. PubMed PMID: 21563754; PubMed Central PMCID: PMC3113728.

17: Groer CE, Tidgewell K, Moyer RA, Harding WW, Rothman RB, Prisinzano TE, Bohn LM. An opioid agonist that does not induce mu-opioid receptor--arrestin interactions or receptor internalization. Mol Pharmacol. 2007 Feb;71(2):549-57. Epub 2006 Nov 7. PubMed PMID: 17090705; PubMed Central PMCID: PMC3926195.

18: Lung D, Wilson N, Chatenet FT, LaCroix C, Gerona R. Non-targeted screening for novel psychoactive substances among agitated emergency department patients. Clin Toxicol (Phila). 2016;54(4):319-23. doi: 10.3109/15563650.2016.1139714. Epub 2016 Feb 5. PubMed PMID: 26846684.

19: Lay J, Carbone SE, DiCello JJ, Bunnett NW, Canals M, Poole DP. Distribution and trafficking of the μ-opioid receptor in enteric neurons of the guinea pig. Am J Physiol Gastrointest Liver Physiol. 2016 Aug 1;311(2):G252-66. doi: 10.1152/ajpgi.00184.2016. Epub 2016 Jun 30. PubMed PMID: 27365337.

20: Tidgewell K, Harding WW, Lozama A, Cobb H, Shah K, Kannan P, Dersch CM, Parrish D, Deschamps JR, Rothman RB, Prisinzano TE. Synthesis of salvinorin A analogues as opioid receptor probes. J Nat Prod. 2006 Jun;69(6):914-8. PubMed PMID: 16792410.