Sumamry
WIN 55,212-2, classified as an aminoalkylindole derivative, exerts effects akin to cannabinoids such as tetrahydrocannabinol (THC) but boasts a distinctly unique chemical structure.
Functionally, WIN 55,212-2 acts as a robust cannabinoid receptor agonist,[6] demonstrating potent analgesic properties in a rat model of neuropathic pain, activating p42 and p44 MAP kinase through receptor-mediated signaling.
At a concentration of 5 μM, WIN 55,212-2 exerts its influence on sperm by inhibiting ATP production in a manner dependent on the CB1 receptor.
Remarkably, WIN 55,212-2, alongside HU-210 and JWH-133, shows promise in mitigating the inflammation induced by amyloid beta proteins associated with Alzheimer’s disease. It not only helps prevent cognitive impairment and the loss of neuronal markers but achieves this anti-inflammatory effect through its agonist action on cannabinoid receptors, curbing microglial activation and consequent inflammation.
When it comes to cannabinoid receptor interaction, WIN 55,212-2 is a full agonist at the CB1 cannabinoid receptor (Ki = 1.9 nM), surpassing THC (Ki = 41 nM) in affinity for this receptor. Additionally, WIN 55,212-2 is an agonist for the PPARα and PPARγ nuclear receptors.
Intriguingly, WIN 55,212-2 influences voluntary wheel running in laboratory mice, with outcomes influenced by genetic factors and sex.
It’s vital to note that in the United States, all CB1 receptor agonists of the 3-(1-naphthyl)indole class, including WIN 55,212-2, are classified as Schedule I Controlled Substances. Furthermore, the substance is illegal in the UK.
Lastly, WIN 55,212-2 serves as a CB2 receptor agonist, and like other cannabinoid CB2 agonists, it contributes significantly to improving cardiac recovery following ischemia/reperfusion (I/R) in the hearts of diabetic fatty rats. This improvement is achieved by restoring coronary perfusion pressure and heart rate to pre-ischaemic levels, effectively restoring the balance between inducible nitric oxide synthase (iNOS) and endothelial nitric oxide synthase (eNOS) in cardiac function.
| Identifiers | |
|---|---|
| IUPAC name | |
| CAS Number | 131543-22-1 |
|---|---|
| PubChem CID | 5311501 |
| IUPHAR/BPS | 733 |
| ChemSpider | 4470978 |
| UNII | 5H31GI9502 |
| ChEBI | CHEBI:73295 |
| ChEMBL | ChEMBL188 |
| CompTox Dashboard (EPA) | DTXSID40894849 |
| Chemical and physical data | |
| Formula | C27H26N2O3 |
| Molar mass | 426.516 g·mol−1 |
FAQ
1. What is WIN 55,212-2?
WIN 55,212-2 is a chemical compound classified as an aminoalkylindole derivative. It is known for producing effects similar to those of cannabinoids like THC but has a distinct chemical structure.
2. How does WIN 55,212-2 affect cannabinoid receptors?
WIN 55,212-2 is a potent cannabinoid receptor agonist, particularly at the CB1 receptor. It binds with high affinity, leading to a range of effects in the body.
3. What are the potential medical applications of WIN 55,212-2?
WIN 55,212-2 has shown promise as a potent analgesic, particularly in a rat model of neuropathic pain. It is being explored for its therapeutic potential in pain management.
4. How does WIN 55,212-2 influence inflammation in Alzheimer’s disease?
WIN 55,212-2, along with other compounds, has demonstrated the ability to prevent inflammation caused by amyloid beta proteins in Alzheimer’s disease. This anti-inflammatory action is attributed to its action on cannabinoid receptors, particularly in reducing microglial activation.
5. What is the legal status of WIN 55,212-2?
In the United States, WIN 55,212-2 is classified as a Schedule I Controlled Substance, as it belongs to the 3-(1-naphthyl)indole class of CB1 receptor agonists. It is also illegal in the United Kingdom.
6. How does WIN 55,212-2 impact cardiac recovery in diabetic fatty rats?
WIN 55,212-2 acts as a CB2 receptor agonist and has been found to improve cardiac recovery after ischemia/reperfusion (I/R) in the hearts of diabetic fatty rats. It restores coronary perfusion pressure and heart rate to pre-ischaemic levels by balancing the expression of inducible nitric oxide synthase (iNOS) and endothelial nitric oxide synthase (eNOS) in the heart.
7. Can WIN 55,212-2 be legally used for medical purposes?
The legal use of WIN 55,212-2 for medical purposes may vary by region and is subject to regulations. It is essential to consult with local authorities and medical professionals for the most accurate and up-to-date information regarding its use.
8. Is WIN 55,212-2 available for research purposes?
WIN 55,212-2 is commonly used in research settings, particularly in studies related to cannabinoid receptors and their effects on the body. Researchers may obtain it for scientific investigations through appropriate channels.
9. Are there any safety considerations when working with WIN 55,212-2?
Researchers and professionals working with WIN 55,212-2 should adhere to strict safety protocols, especially in laboratories. Safety measures and guidelines should be followed to minimize risks.
10. Where can I find more information about WIN 55,212-2 and its research applications?
You can access in-depth information about WIN 55,212-2 by referring to scientific journals, articles, and academic resources in cannabinoid research. Additionally, experts and institutions specializing in this area can provide valuable insights and guidance.
References
- Controlled Drugs and Substance Act – Schedule II. The Government of Canada enforces regulations regarding controlled substances, classifying them under Schedule II of the Controlled Drugs and Substance Act, which includes specific substances and compounds.
- In a study conducted by Michalski and colleagues in 2008, cannabinoids were found to reduce markers of inflammation and fibrosis in pancreatic stellate cells, showcasing their potential in addressing specific health issues.
- Compton and his team, in a 1992 research endeavor, explored a class of compounds known as aminoalkylindole analogs, revealing their cannabimimetic activities that differ structurally from delta 9-tetrahydrocannabinol (THC).
- Ferraro and colleagues, in a study published in 2001, examined how the cannabinoid receptor agonist WIN 55,212-2 regulates glutamate transmission in the cerebral cortex, both in vivo and in vitro.
- In 2002, Zhang and others investigated the in vitro metabolism of R(+)-[2,3-dihydro-5-methyl-3-[(morpholinyl)methyl]pyrrolo [1,2,3-de]1,4-benzoxazinyl]-(1-naphthalenyl) methanone mesylate, a cannabinoid receptor agonist, shedding light on its metabolic pathways.
- Felder and his team, in a 1995 study, compared the pharmacological and signal transduction characteristics of the human cannabinoid CB1 and CB2 receptors, contributing to a better understanding of their functions.
- Meng and colleagues, in 1998, identified an analgesia circuit activated by cannabinoids, offering insights into how these compounds exert pain-relieving effects.
- Herzberg and his team explored the analgesic effects of R(+)-WIN 55,212-2 mesylate, a high-affinity cannabinoid agonist, in a rat model of neuropathic pain, providing valuable information for pain management research.
- In 1995, Bouaboula and colleagues studied the activation of mitogen-activated protein kinases by the stimulation of the central cannabinoid receptor CB1, shedding light on the intracellular signaling pathways influenced by cannabinoids.
- Morgan and his team, in 2012, delved into the impact of Δ9-tetrahydrocannabinol (Δ9-THC) on mouse sperm motility and male fecundity, offering insights into the potential effects of cannabinoids on reproduction.
- Kuster and colleagues, in a 1993 study, examined aminoalkylindole binding in the rat cerebellum and the selective displacement of natural and synthetic cannabinoids, contributing to the understanding of cannabinoid receptors in the brain.
- O’Sullivan, in a 2016 review, provided an update on the activation of peroxisome proliferator-activated receptors (PPARs) by cannabinoids, showcasing their potential role in various physiological processes.
- Keeney and colleagues, in 2012, investigated sex differences in cannabinoid receptor-1 (CB1) pharmacology in mice selectively bred for high voluntary wheel-running behavior, shedding light on how genetic factors and gender may influence cannabinoid responses.
- The United States classifies substances under the Controlled Substances Act, specifically under 21 U.S.C. § 812, which includes various schedules for controlled substances.
- The “Misuse of Drugs Act 1971 (Amendment) Order 2013” in the United Kingdom outlines regulations concerning controlled substances and their legal status.
- González and his team, in a 2011 study, explored the potential of the cannabinoid agonist WIN 55,212-2 in reducing cardiac ischaemia–reperfusion injury in Zucker diabetic fatty rats. They highlighted the role of CB2 receptors and nitric oxide production in this process.
- Shmist and colleagues, in a 2006 study, investigated how delta-9-tetrahydrocannabinol (THC) protects cardiac cells from hypoxia via CB2 receptor activation and nitric oxide production, offering insights into the potential cardiovascular effects of cannabinoids.