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Herkinorin


Herkinorin
Systematic (IUPAC) 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
Identifiers
CAS number	?
ATC code	?
PubChem	?
Chemical data
Formula	C₂₈H₃₀O₈
Mol. mass	494.55 g/mol
Synonyms	Herkinorin
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Legal
Routes	?

Herkinorin is an opioid analgesic that is an analogue of the natural product Salvinorin A. It was discovered in 2005 during structure-activity relationship studies into neoclerodane diterpenes, the family of chemical compounds of which Salvinorin A is a member.^[1]

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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.^[2]^[3] Herkinorin is a semi-synthetic compound made from Salvinorin B, which is made from Salvinorin A, which is extracted from the plant Salvia divinorum.^[4]

Presumably herkinorin produces similar effects to other μ-opioid agonists, such as analgesia and sedation, along with side effects such as nausea, itching, vomiting and respiratory depression which may be harmful or fatal. However unlike most μ-opioid agonists, herkinorin does not promote the recruitment of β-arrestin-2 to the intracellular domain of the μ-opioid receptor, and so does not induce receptor internalisation.^[5] This means that herkinorin may not produce tolerance and dependence in the same way as other opioids, although some development of tolerance through other mechanisms has been observed.^[6]

References

^ Harding WW, Tidgewell K, Byrd N, Cobb H, Dersch CM, Butelman ER, Rothman RB, Prisinzano TE. Neoclerodane diterpenes as a novel scaffold for mu opioid receptor ligands. Journal of Medicinal Chemistry. 2005 Jul 28;48(15):4765-71.
^ 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. Journal of Natural Products. 2006 Jun;69(6):914-8.
^ 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. Bioorganic and Medicinal Chemistry Letters. 2007 Nov 15;17(22):6111-5.
^ Tidgewell K, Harding WW, Schmidt M, Holden KG, Murry DJ, Prisinzano TE. Bioorganic and Medicinal Chemistry Letters. 2004; 14: 5099-5102.
^ Groer CE, Tidgewell K, Moyer RA, Harding WW, Rothman RB, Prisinzano TE, Bohn LM. An opioid agonist that does not induce μ-opioid receptor--arrestin interactions or receptor internalization. Molecular Pharmacology. 2007 Feb;71(2):549-57.
^ 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.

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