Incarvillateine CAS No. 145307-22-8

Product Description

Incarvillateine is a monoterpenoid indole alkaloid first isolated from Incarvillea sinensis, a traditional Chinese medicinal plant long employed to ease rheumatic pain and inflammation. Possessing a distinctive cyclopenta[b]pyran core, the compound has drawn modern scientific scrutiny because its analgesic potency rivals morphine yet is accompanied by markedly lower risks of respiratory depression, tolerance or addiction. Rather than acting through opioid receptors, incarvillateine appears to relieve pain primarily by activating adenosine A₁ and A₂A receptors—an unusual mechanism that also underlies its mild motor-suppressive effects. Beyond analgesia, early data hint at anti-inflammatory and antispasmodic activities, positioning incarvillateine as a promising lead for next-generation, non-opioid pain therapeutics, though rigorous clinical studies are still required to confirm its safety and efficacy in humans.

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Product Use & Characteristics

Chemical Identity & Structure

• Classification: Monoterpene alkaloid (dimeric, with a cyclobutane ring and 3-methoxy phenyl moiety).

• Source: Incarvillea sinensis (Bignoniaceae), a traditional Chinese medicinal herb ("jiao-hao").

• Key Structural Features:

  • Dimeric scaffold with five contiguous stereocenters.

  • Cyclobutane ring (essential for antinociceptive activity).

  • Truxillic acid-like moiety (in derivatives for enhanced antinociception).

Pharmacological Properties

• Mechanism of Action:

  • Adenosine receptor (AR) agonist, primarily targeting A1 and A3 subtypes.

  • Non-opioid pathway (naloxone-insensitive).

  • Anti-inflammatory: Reduces IL-1β and edema in CFA-induced inflammation.

• Efficacy:

  • Neuropathic pain: Reverses paclitaxel- and SNI-induced mechanical allodynia.

  • Inflammatory pain: Attenuates CFA-induced thermal hyperalgesia.

  • Acute pain: Weak/no effect in hot-plate tests (selective for pathological pain).

• Safety:

  • No tolerance after 7-day dosing.

  • No motor impairment (rotarod/locomotor tests).

Uses (Therapeutic Applications)

• Primary: Analgesic for neuropathic and inflammatory pain (e.g., chemotherapy-induced neuropathy, rheumatism).

• Lead compound:

  • Template for non-opioid antinociceptive agents.

  • Derivatives (e.g., truxillic acid-modified incarvillateines) under development to mitigate neuroinflammation risks.

Synthesis Methods

• Total Synthesis:

  • Enantioselective synthesis via Rh-catalyzed olefinic C–H activation or intramolecular alkylation.

  • Key steps:

    1. Photoisomerization of cinnamic acid derivatives.

    2. Cavitand-mediated photodimerization to form cyclobutane core.

• Semi-synthesis: Modifications of natural incarvillateine (e.g., truxillic acid conjugation).

Challenges & Future Directions

• Limitations: Suspected neuroinflammation in native form; derivatives under study.

• Research gaps:

  • In vitro AR binding confirmation (A3AR affinity via 3-methoxy phenyl dimers).

  • Structure-activity relationships for safer analogs.

Why us!

Qingdao Sigma Chemical Co., Ltd., established in January 2017 and headquartered in Qingdao, China, is a reliable chemical supplier. Specializing in pharmaceuticals, biochemical intermediates, and research chemicals, the company offers a diverse product portfolio, including peptides (e.g., Tirzepatide, Semaglutide), nootropics, veterinary products, and APIs, often marketed with ≥99% purity and COA certification. We provides R&D, custom synthesis, and contract manufacturing services at various scales, while claiming a global export presence across 100+ countries. With international warehouses in the USA, Europe, Australia, and Canada, Qingdao Sigma Chemical also facilitates drop-shipping and reshipments, positioning itself as a key supplier for laboratory and research applications.