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Product name: AM2201

CAS: 335161-24-5

MF: C24H22FNO

MW: 359.44

EINECS:

MDL Number:MFCD16620503

Synonyms:AM-2201 (AM 2201;[1-(5-fluoropentyl)-1H-indole-3-yl](naphthalene-1-yl)methanone;AM-2201 (1-[(5-fluoropentyl)-1H-indol-3-yl]-(naphthalen-1-yl)methanone);1-(5-Fluoropentyl)-3-(1-naphthoyl)-1H-indole;1-(5-fluoropentyl)-3-[(naphthalen-1-yl)carbonyl]-1H-indole;(1-(5-Fluoropentyl)-3-(naphthalen-1-oyl)indole);(1-(5-fluoropentyl)-1H-indol-3-yl)(naphthalen-1-yl)Methanone;1-(5-fluoropentyl)-3-(naphtalen-1-oy)indole

AM2201 is a potent synthetic cannabinoid (CB) with Ki values of 1.0 and 2.6 nM for the CB1 and CB2 receptors, respectively. The physiological actions and metabolism of AM2201 have not been characterized.

This product is a qualified Reference Material (RM) that has been manufactured and tested to meet ISO17025 and Guide 34 guidelines. These materials are tested using validated analytical methods on qualified instrumentation to ensure traceability of measurements. All traceable RMs may be distinguished by their CofAs and can be downloaded below using the batch number located on the product label. For a representative CofA please contact our technical support.

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Novel synthetic cannabinoids are appearing in recreational drug markets worldwide. Pharmacological characterization of these new drugs is needed to inform clinicians, toxicologists, and policy makers who monitor public health. [1-(5-Fluoropentyl)-1H-indol-3-yl](1-naphthyl)methanone (AM-2201) is an abused synthetic cannabinoid that was initially created as a research tool for investigating the endocannabinoid system.

Here we measured the pharmacodynamic effects of AM-2201 in rats, and simultaneously determined plasma pharmacokinetics for the parent drug and its metabolites. 

Male Sprague-Dawley rats were fitted with surgically implanted temperature transponders and indwelling jugular catheters under pentobarbital anesthesia.

One week later, rats received subcutaneous injection of AM-2201 (0.1, 0.3, and 1.0 mg/kg) or its vehicle, and serial blood specimens were withdrawn via catheters. Core temperatures and catalepsy were measured just prior to each blood withdrawal, and plasma was assayed for drug and metabolites using liquid chromatography-tandem mass spectrometry. 

We found that AM-2201 produced dose-related hypothermia and catalepsy that peaked at 2 hours and lasted up to 8 hours. AM-2201 plasma concentrations rose linearly with increasing dose and ranged from 0.14 to 67.9 µg/l. Concentrations of three metabolites, AM-2201 N-(4-hydroxypentyl) (≤0.17 µg/l), naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) N-(5-hydroxypentyl) (≤1.14 µg/l), and JWH-018 N-pentanoic acid (≤0.88 µg/l) were detectable but much lower. Peak AM-2201, JWH-018 N-(5-hydroxypentyl), and JWH-018 N-pentanoic acid concentrations occurred at 1.3, 2.4, and 6.5 hours, respectively.

Concentrations of AM-2201, JWH-018 N-(5-hydroxypentyl), and JWH-018 N-pentanoic acid were negatively correlated with body temperature, but, given the low concentrations of metabolites detected, AM-2201 is likely the major contributor to pharmacodynamic effects under our experimental conditions.

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[1-(5-Fluoropentyl)-1H-indol-3-yl](1-naphthyl)methanone (AM-2201) is a synthetic cannabinoid that was first developed in 2000 as a pharmacological tool to study the endocannabinoid system (Fig. 1) (Makriyannis and Deng, 2000).

AM-2201 is a full agonist at cannabinoid-1 receptors (CB1Rs) (Chimalakonda et al., 2012), producing psychoactive effects similar to the phytocannabinoid Δ9-tetrahydrocannabinol (Huestis et al., 2001), but with a binding affinity 40 times higher (Makriyannis and Deng, 2000; Chimalakonda et al., 2012). Similarly, the binding affinity of AM-2201 at cannabinoid-2 receptors, which are responsible for cannabinoid-mediated peripheral effects, is 14 times higher than that of Δ9-tetrahydrocannabinol (Makriyannis and Deng, 2000).

Smoking is the predominant route of AM-2201 consumption, and typical smoked doses of 250 µg to 2 mg are estimated from online drug forums . By contrast, a 5-mg AM-2201 oral dose was reported as a “comfortable entry dose,” whereas 10 mg would be “powerful” [1-(5-Fluoropentyl)-1H-indol-3-yl](1-naphthyl)methanone (AM-2201) is a synthetic cannabinoid that was first developed in 2000 as a pharmacological tool to study the endocannabinoid system (Fig. 1) (Makriyannis and Deng, 2000). AM-2201 is a full agonist at cannabinoid-1 receptors (CB1Rs) (Chimalakonda et al., 2012), producing psychoactive effects similar to the phytocannabinoid Δ9-tetrahydrocannabinol (Huestis et al., 2001), but with a binding affinity 40 times higher (Makriyannis and Deng, 2000; Chimalakonda et al., 2012).

Similarly, the binding affinity of AM-2201 at cannabinoid-2 receptors, which are responsible for cannabinoid-mediated peripheral effects, is 14 times higher than that of Δ9-tetrahydrocannabinol (Makriyannis and Deng, 2000). Smoking is the predominant route of AM-2201 consumption, and typical smoked doses of 250 µg to 2 mg are estimated from online drug forums . By contrast, a 5-mg AM-2201 oral dose was reported as a “comfortable entry dose,” whereas 10 mg would be “powerful” . These dose differences indicate potential AM-2201 degradation in the stomach, limited gastrointestinal absorption, or extensive gastrointestinal or hepatic metabolism. AM-2201 consumption induces typical cannabimimetic effects such as dry mouth, nausea, drowsiness, confusion, mydriasis, and tachycardia (Holm et al., 2013; Celofiga et al., 2014; Elian and Hackett, 2014; Musshoff et al., 2014; WHO, 2014). 

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At higher doses, psychiatric and autonomic complications, such as extreme anxiety, acute psychosis, hyperemesis, and convulsions are reported (Patton et al., 2013; Celofiga et al., 2014).. These dose differences indicate potential AM-2201 degradation in the stomach, limited gastrointestinal absorption, or extensive gastrointestinal or hepatic metabolism.

AM-2201 consumption induces typical cannabimimetic effects such as dry mouth, nausea, drowsiness, confusion, mydriasis, and tachycardia (Holm et al., 2013; Celofiga et al., 2014; Elian and Hackett, 2014; Musshoff et al., 2014; WHO, 2014). At higher doses, psychiatric and autonomic complications, such as extreme anxiety, acute psychosis, hyperemesis, and convulsions are reported (Patton et al., 2013; Celofiga et al., 2014).

Considering the potential risks associated with AM-2201 intake, pharmacodynamic and pharmacokinetic studies are needed to document consumption in clinical and forensic cases. In vitro and in vivo animal and human experiments identified six major AM-2201 metabolites: AM-2201 N-(4-hydroxypentyl), AM-2201 6′-hydroxyindole, naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) N-(5-hydroxypentyl), JWH-018 N-pentanoic acid, naphthalen-1-yl-(1-butylindol-3-yl)methanone (JWH-073) N-(4-hydroxybutyl), and JWH-073 N-butanoic acid (Chimalakonda et al., 2012; Sobolevsky et al., 2012; Hutter et al., 2013; Elian and Hackett, 2014; Jang et al., 2014; Kim et al., 2015). 

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AM-2201 and metabolite blood concentrations generally range from <0.1 to 12 µg/l in humans, with JWH-018 N-(5-hydroxypentyl) and JWH-018 N-pentanoic acid as principal metabolites (Fig. 1) (Holm et al., 2013; Hutter et al., 2013; Kneisel et al., 2013; Patton et al., 2013; Wikstrom et al., 2013; Yeakel and Logan, 2013; Musshoff et al., 2014; Tuv et al., 2014; World Health Organization, 2014). Importantly, AM-2201 is not detected in human urine. In a preclinical study, AM-2201 6′-hydroxyindole and JWH-018 N-pentanoic acid were the main AM-2201 metabolites in rat urine after repeated intraperitoneal injections of high drug doses (15 mg/kg) (Jang et al., 2014). To date, only one AM-2201 pharmacokinetic study is reported in the literature.

AM-2201 kinetics were reported from a single case of human oral self-administration (0.07 mg/kg), where AM-2201 and metabolite elimination from blood and urine were followed for up to 267 hours postadministration. However, AM-2201 and JWH-018 N-(5-hydroxypentyl) kinetic profiles were incomplete as maximum concentrations were not captured (Hutter et al., 2013).

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Pharmacodynamic effects of cannabinoids in rodents can be evaluated by standard tests examining physiologic parameters and behavioral endpoints. The “cannabinoid tetrad” is a set of tests to identify CB1R activation that usually includes the measurement of hypothermia, catalepsy, reduction in motor activity, and antinociceptive effects (Smith et al., 1994; Ovadia et al., 1995; McGregor et al., 1996; Stein et al., 1996; Rawls et al., 2002; Brents et al., 2011, 2012; Banister et al., 2015a,b).

In 2015, the first AM-2201 study in rats demonstrated that intraperitoneal injection of 0.3, 1.0, and 3.0 mg/kg produced robust dose-related hypothermia (Banister et al., 2015b), and we confirmed these findings using subcutaneous administration of the drug to rats (Schindler et al., 2017). The metabolites AM-2201 N-(4-hydroxypentyl) and JWH-018 N-(5-hydroxypentyl) are known to be CB1R full agonists (Brents et al., 2011; Chimalakonda et al., 2012), and these compounds may contribute to the effects of AM-2201 consumption. 

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The relationships between AM-2201 metabolite blood concentrations and cannabinoid effects has yet to be determined. Given the scarcity of pharmacological data for AM-2201, we investigated AM-2201 pharmacodynamics and pharmacokinetics after injections of AM-2201 (0.1, 0.3, and 1.0 mg/kg, s.c.) in male rats fitted with temperature transponders and indwelling jugular catheters.

We measured body temperature and catalepsy at timed intervals postinjection, while simultaneously obtaining serial blood specimens for analysis of AM-2201 and its metabolites using liquid chromatography tandem mass spectrometry (LC-MS/MS) (Carlier et al., 2016).

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