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Herkinorin

Item No. 20925

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(benzoyloxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid, methyl ester
CAS Number
862073-77-6
Molecular Formula
C28H30O8
Formula Weight
494.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: 1 mg/mlDMF: 1 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 2 mg/ml
λmax
228 nm
SMILES
O=C(O[C@H]1C[C@@H](C(OC)=O)[C@@](CC[C@]2([H])[C@]3(C)C[C@@H](C4=COC=C4)OC2=O)(C)[C@]3([H])C1=O)C5=CC=CC=C5
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/t18-,19-,20-,21-,23-,27-,28-/m0/s1
InChi Key
PYDQMXRFUVDCHC-XAGHGKQISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Herkinorin (Item No. 20925) is an analytical reference standard that is functionally categorized as an opioid. It is a natural neoclerodane diterpene from S. divinorum that preferentially activates the µ-opioid receptor.1,2 Unlike the peptide DAMGO (Item No. 21553), herkinorin activates µ-opioid receptors without inducing arrestin-mediated receptor internalization.1,3 Herkinorin has antinociceptive effects in rats.4 It has been identified as a novel psychoactive substance in multiple agitated emergency department patients screened in a non-targeted manner.5 This product is intended for research and forensic applications.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Groer, C.E., Tidgewell, K., Moyer, R.A., et al. An opioid agonist that does not induce m-opioid receptor-arrestin interactions or receptor internalization. Mol. Pharmacol. 71(2), 549-557 (2006).

    2. Holden, K.G., Tidgewell, K., Marquam, A., et al. Synthetic studies of neoclerodane diterpenes from Salvia divinorum: Exploration of the 1-position. Bioor. Med. Chem. Lett. 17(22), 6111-6115 (2007).

    3. Xu, H., Partilla, J.S., Wang, X., et al. A comparison of noninternalizing (herkinorin) and internalizing (DAMGO) m-opioid agonists on cellular markers related to opioid tolerance and dependence. Synapse 61(3), 166-175 (2007).

    4. Lamb, K., Tidgewell, K., Simpson, D.S., et al. 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. 121(3), 181-188 (2012).

    5. Lung, D., Wilson, N., Chatenet, F.T., et al. Non-targeted screening for novel psychoactive substances among agitated emergency department patients. Clin. Toxicol. (Phila) 54(4), 319-323 (2016).