3D model (JSmol)
|Molar mass||448.603 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Pawhuskin A is a naturally occurring prenylated stilbene isolated from Dalea purpurea which acts as a competitive silent antagonist of the κ-, μ-, and δ-opioid receptors (Ke = 203 nM, 570 nM, and 2900 nM, respectively). The compound was named after Pawhuska, Oklahoma, a place near where the samples of Dalea purpurea that led to its discovery were taken from. Other isolates of the plant with affinity for opioid receptors include Pawhuskin B and Pawhuskin C, though these compounds produce comparatively weak opioid receptor displacement (4.2–11.4 μM) relative to Pawhuskin A. Dalea purpurea was used in traditional Native American medicine to treat various ailments, and pawhuskin A and related isolates may be some of the constituents of the plant which underlay this use.
- Belofsky G, French AN, Wallace DR, Dodson SL (January 2004). "New geranyl stilbenes from Dalea purpurea with in vitro opioid receptor affinity". J. Nat. Prod. 67 (1): 26–30. doi:10.1021/np030258d. PMID 14738380.
- Neighbors JD, Buller MJ, Boss KD, Wiemer DF (November 2008). "A concise synthesis of pawhuskin A". J. Nat. Prod. 71 (11): 1949–52. doi:10.1021/np800351c. PMC 6679901. PMID 18922035.
- Hartung AM, Beutler JA, Navarro HA, Wiemer DF, Neighbors JD (February 2014). "Stilbenes as κ-selective, non-nitrogenous opioid receptor antagonists". J. Nat. Prod. 77 (2): 311–9. doi:10.1021/np4009046. PMC 3993902. PMID 24456556.
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