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80-578: Nabilone , sold under the brand name Cesamet among others, is a synthetic cannabinoid with therapeutic use as an antiemetic and as an adjunct analgesic for neuropathic pain . It mimics tetrahydrocannabinol (THC), the primary psychoactive compound found naturally occurring in Cannabis . The Food and Drug Administration (FDA) in the United States has indicated nabilone for chemotherapy-induced nausea/vomiting. In other countries, such as Canada , it

160-494: A "marijuana-like-high" would follow his recipes and methods. Eicosanoid synthetic cannabinoids are analogs of endocannabinoids , such as anandamide . Endocannabinoids are cannabinoids naturally occurring in the body. One of the best known synthetic analogs of anandamide is methanandamide . The synthetic cannabinoids that have emerged recently have even greater structural diversity, possibly to subvert legal regulations on earlier generations of synthetic cannabinoids. There are

240-510: A chemical reaction that makes a chiral product will always yield a racemate. That can make the synthesis of a racemate cheaper and easier than making the pure enantiomer, because it does not require special conditions. This fact also leads to the question of how biological homochirality evolved on what is presumed to be a racemic primordial earth. The reagents of, and the reactions that produce, racemic mixtures are said to be "not stereospecific " or "not stereoselective ", for their indecision in

320-426: A condition where the blood's ability to clot is impaired. 2 deaths and over 41 hospitalizations have been directly linked to this specific outbreak as of December 16, 2021. Synthetic cannabinoids have been speculated to be involved in vaping-associated pulmonary injury (VAPI). The Austrian Ministry of Health announced on December 18, 2008, that Spice would be controlled under Paragraph 78 of their drug-law on

400-458: A derivative of HU-210 , is a hybrid cannabinoid because it has the dibenzopyran ring common of classical cannabinoids and an aliphatic hydroxyl group common in the CP family of nonclassical cannabinoids. Aminoalkylindoles are structurally dissimilar to THC and include naphthoylindoles ( JWH-018 ), phenylacetylindoles ( JWH-250 ), and benzoylindoles ( AM-2233 ). Aminoalkylindoles are considered to be

480-441: A dibenzopyran ring. They were developed starting in the 1960s, following the isolation of THC, and were originally the only cannabinoids synthesized. Classical cannabinoids include nabilone and dronabinol , and one of the best known synthetic classical cannabinoids is HU-210 . HU-210 is a chiral compound first synthesized by Raphael Mechoulam at Hebrew University in the 1980s. It was discovered in herbal incense products by

560-587: A family history of mental illness . Individuals with risk factors for psychotic disorders are often counseled against using synthetic cannabinoids. Psychiatrists have suggested that the lack of an antipsychotic chemical, like CBD in natural cannabis , may make synthetic cannabinoids more likely to induce psychosis than natural cannabis. There are five major categories for synthetic cannabinoids: classical cannabinoids, non-classical cannabinoids, hybrid cannabinoids, aminoalkylindoles , and eicosanoids . Classical cannabinoids are analogs of THC that are based on

640-431: A few different structural classifications of synthetic cannabinoids that include many of the new structures, some of which are shown in table one. The indazole carboxamide group, including APINACA (AKB-48), an adamantyl indazole carboxamide, and AB-PINACA , an aminocarbonyl indazole carboxamide, is an example of a new group of synthetic cannabinoids. Most clandestine manufacturers and producers only make small changes to

720-426: A height, and wandering into traffic; cardiovascular effects; and central nervous system depression . Researchers have pointed out a few ways that synthetic cannabinoids differ from marijuana, and therefore may be more dangerous. First, they often have greater intrinsic activity . Many of the synthetic cannabinoids are full agonists of the cannabinoids receptors , CB 1 and CB 2 , compared to THC , which

800-411: A higher cost in cases where the use requires specifically one isomer (e.g., for a stereospecific reagent); compare omeprazole and esomeprazole . Moving from a racemic drug to a chiral specific drug may be done for a better safety profile or an improved therapeutic index. This process is called chiral switching and the resulting enantiopure drug is called a chiral switch . As examples, esomeprazole

880-450: A particular stereoisomerism . A frequent scenario is that of a planar species (such as an sp carbon atom or a carbocation intermediate) acting as an electrophile. The nucleophile will have a 50% probability of 'hitting' either of the two sides of the planar grouping, thus producing a racemic mixture: Some drug molecules are chiral, and the enantiomers have different effects on biological entities. They can be sold as one enantiomer or as

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960-517: A racemate sometimes has different properties from either of the pure enantiomers. Different melting points are most common, but different solubilities and boiling points are also possible. Pharmaceuticals may be available as a racemate or as the pure enantiomer, which might have different potencies. Because biological systems have many chiral asymmetries, pure enantiomers frequently have very different biological effects; examples include glucose and methamphetamine . There are four ways to crystallize

1040-406: A racemate; three of which H. W. B. Roozeboom had distinguished by 1899: The separation of a racemate into its components, the individual enantiomers, is called a chiral resolution . Various methods exist for this separation, including crystallization, chromatography , and the use of various reagents. Without a chiral influence (for example a chiral catalyst , solvent or starting material),

1120-478: A racemic mixture. Examples include thalidomide , ibuprofen , cetirizine and salbutamol . A well known drug that has different effects depending on its ratio of enantiomers is amphetamine . Adderall is an unequal mixture of both amphetamine enantiomers. A single Adderall dose combines the neutral sulfate salts of dextroamphetamine and amphetamine, with the dextro isomer of amphetamine saccharate and D/L-amphetamine aspartate monohydrate. The original Benzedrine

1200-429: A range of 1.1–1.5 ng/mL of 5F-PB-22 . Three of the four cases were sudden episodes and the symptoms leading to death included acute shortness of breath; vasocongestion in the liver, spleen, and kidneys; bilateral pulmonary edema ; dead inflamed tissue (necrotizing granulomatous inflammation); and congestion of most internal organs. The fourth case presented to the hospital with severe problems that deteriorated over

1280-472: A slower onset of peak action and a greater dose-dependence of effects, which the investigators attributed to greater bioavailability. A study comparing nabilone with metoclopramide , conducted before the development of modern 5-HT 3 antagonist anti-emetics such as ondansetron , revealed that patients taking cisplatin chemotherapy preferred metoclopramide , while patients taking carboplatin preferred nabilone to control nausea and vomiting. Nabilone

1360-498: A strong compulsion to re-dose, withdrawal symptoms , and persistent cravings. There have been several deaths linked to synthetic cannabinoids. The Centers for Disease Control and Prevention (CDC) found that the number of deaths from synthetic cannabinoid use tripled between 2014 and 2015. In 2018, the United States Food and Drug Administration warned of significant health risks from synthetic cannabinoid products that contain

1440-422: A suitable replacement for the naphthoyl moiety that is currently regulated by US scheduling laws . Although most synthetic cannabinoids are not direct analogs of THC, they share many common features with THC. Most are lipid-soluble , non-polar , small molecules (usually 20–26 carbon atoms) that are fairly volatile , making them "smokable", like THC. Another common feature of most synthetic cannabinoids and THC

1520-520: A synthetic cannabinoid called 5F-ADB over one weekend in July 2018. The Department of Public Health released that they believe "5F-ADB was the primary cause of the cluster of patients with these adverse drug reactions." On December 10, 2021, the Hillsborough County, Florida department of health reported cases of "rat poison" contaminated synthetic blends linked to symptoms associated with coagulopathy,

1600-840: A synthetic cannabinoid, either AMB-FUBINACA or AB, in Christchurch over two days. Some of the people were in critical condition in the Intensive Care Unit . On October 20, 2011, the Louisiana State University football program announced that it had suspended three players, including star cornerback Tyrann Mathieu , who tested positive for synthetic cannabinoids. On July 12, 2016, 33 people were intoxicated by an herbal "incense" product called "AK-47 24 Karat Gold", and dozens overdosed , in Brooklyn . Eighteen people were transported to local hospitals. The herbal "incense" product

1680-440: A variety of other designer drugs, has been illegal. Racemic mixture In chemistry , a racemic mixture or racemate ( / r eɪ ˈ s iː m eɪ t , r ə -, ˈ r æ s ɪ m eɪ t / ) is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. The first known racemic mixture

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1760-468: A wide array of plants. However, oftentimes, none of the listed ingredients have been detectable. Herbal components of 'Spice' (a non-exhaustive list): Many of the early synthetic cannabinoids that were synthesized for use in research were named after either the scientist who first synthesized them or the institution or company where they originated. Some of the names of synthetic cannabinoids synthesized for recreational use were given names to help market

1840-699: Is a NMDA receptor antagonist and is largely inactive as a cannabinoid . On the other hand, aminoalkylindoles , eicosanoids , and the other new synthetic cannabinoid groups typically do not have an asymmetric center, so they are usually not stereospecific. Recently there has been an increase in the emergence of terminally fluorinated synthetic cannabinoids, such as 5F-PB-22 (fluorinated version of PB-22 ) and XLR-11 (fluorinated version of UR-144 ). South Korea's National Forensic Service reported that 90% of all seized synthetic cannabinoids in 2013 were fluorinated, compared to no fluorinated synthetic cannabinoids reported in 2010. 5F-derivations (terminal fluorination) of

1920-408: Is a partial agonist of the cannabinoid CB 1 and CB 2 receptors . Nabilone is given in 1 or 2 mg doses multiple times a day up to a total of 6 mg. It is completely absorbed from oral administration and highly plasma protein bound . Multiple cytochrome P450 enzymes extensively metabolize nabilone to various metabolites that have not been fully characterized. Nabilone

2000-526: Is a racemic mixture consisting of ( S , S )-(+)- and ( R , R )-(−)- isomers . Nabilone was originally developed by Eli Lilly and Company ; and was first approved by Health Canada in 1981; shortly followed by its approval in Mexico , the United Kingdom , and Germany . Lilly received FDA approval in 1985 to market it, but withdrew that approval in 1989 for commercial reasons. Valeant Pharmaceuticals acquired

2080-416: Is a chiral switch of (±)-omeprazole and levocetirizine is a chiral switch of (±)-cetirizine. While often only one enantiomer of the drug may be active, there are cases in which the other enantiomer is harmful, like salbutamol and thalidomide . The (R) enantiomer of thalidomide is effective against morning sickness, while the (S) enantiomer is teratogenic, causing birth defects. Since the drug racemizes,

2160-423: Is a side-chain of five to nine saturated carbon atoms. It has been found that this chain of carbons is required for optimal psychotropic activity from binding CB 1 receptors . Also, most synthetic cannabinoids are agonists of both cannabinoid receptors , CB 1 and CB 2 , like THC; however, they often have greater binding affinity and therefore greater potency than THC, as seen in table two. Due to

2240-492: Is called “grape acid” e.g. German traubensäure and Swedish druvsyra . Carl von Linné gave red elderberry the scientific name Sambucus racemosa as the Swedish name, druvfläder , means 'grape elder', so called because its berries grow in a grape-like cluster. A racemic mixture is denoted by the prefix (±)- or dl- (for sugars the prefix dl - may be used), indicating an equal (1:1) mixture of dextro and levo isomers. Also

2320-468: Is controversial and, according to Lewis Nelson, a medical toxicologist at the NYU School of Medicine, a mistake. Nelson claims that relative to marijuana , products containing synthetic cannabinoids "are really quite different, and the effects are much more unpredictable. It's dangerous". Since the term synthetic does not apply to the plant, but rather to the cannabinoid that the plant contains ( THC ),

2400-473: Is most often used for confirmation and quantitation. There are commercially available EMIT kits for the screening of the synthetic cannabinoids JWH-018 , JWH-073 , JWH-398 , JWH-200 , JWH-019 , JWH-122 , JWH-081 , JWH-250 , JWH-203 , CP-47,497 , CP-47,497-C8 , HU-210 , HU-211 , AM-2201 , AM-694 , RCS-4 , and RCS-8 through companies like NMS Labs, Cayman Chemical, and Immunoanalysis Corporation. In September 2018, at least 10 people overdosed on

2480-454: Is only a partial agonist . Secondly, they may have other actions in the body, in addition to activating cannabinoid receptors. Some may work on NMDA glutamate receptors. Some may also work on serotonin , either indirectly by inhibiting MAO and increasing 5-HT 1A expression , or by directly binding to serotonin receptors, including the 5-HT 1A and 5-HT 3 subtypes; some researchers speculate that this activity may be because

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2560-641: Is sometimes used for nightmares in post-traumatic stress disorder , but there have not been studies longer than nine weeks, so effects of longer-term use are not known. Nabilone has also been used for medication overuse headache. Nabilone can increase – rather than decrease – postoperative pain . In the treatment of fibromyalgia , adverse effects limit the useful dose. Adverse effects of nabilone include, but are not limited to: dizziness / vertigo , euphoria , drowsiness , dry mouth , ataxia , sleep disturbance , headache , nausea , disorientation , depersonalization , hallucinations , and asthenia . Nabilone

2640-420: Is widely used as an adjunct therapy for chronic pain management . Numerous trials and case studies have demonstrated modest effectiveness for relieving fibromyalgia and multiple sclerosis . Nabilone is used to treat nausea and vomiting in people under chemotherapy . Nabilone has shown modest effectiveness in relieving fibromyalgia . A 2011 systematic review of cannabinoids for chronic pain determined there

2720-470: The U.S. Customs and Border Protection in January 2009; however, classical cannabinoids are not often seen in synthetic cannabinoid blends for recreational use , likely because they are difficult to synthesize. Non-classical cannabinoids include cyclohexylphenols (CP), which were first synthesized in the late 1970s to 1980s by Pfizer as potential analgesics . The C8 homologue of CP-47,497 ( CP-47,497-C8 )

2800-608: The Wisconsin Department of Health Services confirmed 16 more cases, bringing the total number of people affected by the outbreak in Wisconsin to 80 people since March 2018, including one death in July 2018. In August 2018, there were almost one hundred overdose cases reported over two days in New Haven, Connecticut from a bad batch of K2. The synthetic cannabinoid was believed to have been mixed with fentanyl , although no fentanyl

2880-570: The cannabinoid receptors . They have been designed to be similar to THC , the natural cannabinoid with the strongest binding affinity to the CB 1 receptor , which is linked to the psychoactive effects or "high" of marijuana . These synthetic analogs often have greater binding affinity and greater potency to the CB 1 receptors. There are several synthetic cannabinoid families (e.g., AM- xxx , CP- xx,xxx , HU- xx , JWH- xxx ) which are classified by

2960-466: The endocannabinoids that activate them in the body. Synthetic cannabinoids were needed partly due to legal restrictions on natural cannabinoids, which make them difficult to obtain for research. Many have been useful because they bind selectively to either the CB1 or CB2 receptors, whereas THC has a similar affinity for both. Tritium -labelled cannabinoids such as CP-55,940 were instrumental in discovering

3040-425: The indole moiety that some synthetic cannabinoids possess is similar to the structure of serotonin. Third, synthetic cannabinoids may break down into metabolites, or create other by-products when heated, that may differ from marijuana. Phase 1 metabolism of JWH-018 results in at least nine monohydroxylated metabolites , three of which have been shown to be full agonists of the CB 1 receptors , compared to

3120-421: The metabolism of THC , which only results in one psychoactive monohydroxylated metabolite. The metabolite N-(3-hydroxypentyl) JWH-018 was found to have toxic effects that its parent compound does not. Some metabolites even appear to be cannabinoid antagonists . Lastly, they may contain unwanted substances, be mislabeled, or contain different doses than advertised (in one analysis, a difference of one log unit

3200-556: The "synthetic cannabinoids" but as a "synthetic phytocannabinoid". In the early 2000s, synthetic cannabinoids began to be used for recreational drug use in an attempt to get similar effects to cannabis . Because synthetic cannabinoid molecular structures differ from THC and other illegal cannabinoids, synthetic cannabinoids were not technically illegal. Since the discovery of the use of synthetic cannabinoids for recreational use in 2008, some synthetic cannabinoids have been made illegal , but new analogs are continually synthesized to avoid

3280-409: The 1–10 μg/L range during the first few hours after recreational usage and the metabolites are usually present in urine at similar concentrations. Little to no parent drug is present in urine, so there is a lot of research to try and identify the major urinary metabolites that could be used as markers of synthetic cannabinoid intake. The major urinary metabolites in most cases are formed by oxidation of

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3360-444: The US that caused coagulopathy (prolonged or excessive bleeding) and resulted in the treatment of over 300 people and at least eight deaths. One of the most common non-cannabinoid ingredients in these products is oleamide , a fatty acid derivative that acts similarly to a cannabinoid and has hypnotic properties. Analysis of 44 products synthetic cannabinoid revealed oleamide in 7 of

3440-643: The United States advising of 89 confirmed cases of "serious unexplained bleeding" in Illinois. The cases are still being studied; however, 63 of the patients reported synthetic cannabinoid use, and laboratory analysis confirmed brodifacoum was present in at least 18 patients. As of April 24, 2018, 153 cases, including four deaths, linked to this outbreak have been reported to the Illinois Department of Public Health (IDPH) since March 7, 2018. On September 18, 2018,

3520-612: The alkyl side-chain to an alcohol and carboxylic acid followed by glucuronide conjugation and also by N-dealkylation and aromatic hydroxylation. For example, the main metabolites of JWH-018 , of which there are over 20, include carboxylated, monohydroxylated, dihydroxylated, and trihydroxylated metabolites, but they are mostly excreted in urine as glucuronide conjugates. The presence of synthetic cannabinoids or their metabolites in bodily fluids may be determined using specifically targeted commercially available immunoassay screening methods (EMIT), while liquid chromatography-mass spectrometry

3600-576: The brand name Spice, were first released in 2005 by the now-dormant company the Psyche Deli in London. In 2006, the brand gained popularity. According to the Financial Times , the assets of the Psyche Deli rose from £65,000 in 2006 to £899,000 in 2007. The EMCDDA reported in 2009 that Spice products were identified in 21 of the 30 participating countries. Because of these controversies, and in particular

3680-406: The cannabinoid receptors in the early 1990s. Some early synthetic cannabinoids were also used clinically. Nabilone , a first generation synthetic THC analog, has been used as an antiemetic to combat vomiting and nausea since 1981. Synthetic THC (marinol, dronabinol ) has been used as an antiemetic since 1985, and an appetite stimulant since 1991, although synthetic THC is often not listed among

3760-488: The combination of O -desmethyltramadol , a μ- opioid agonist and analgesic drug, and kratom , an Asiatic medicinal plant containing mitragynine , another μ- opioid agonist , in a synthetic cannabinoid product called "Krypton". And in 2013, AH-7921 was detected in smoking blends in Japan. In 2018, there was an outbreak of synthetic cannabinoids contaminated with anticoagulants , mainly brodifacoum , in at least 11 states in

3840-709: The course of a day, ending with circulatory , respiratory , central nervous system , and renal failure . There have been reports of a strong compulsion to re-dose, withdrawal symptoms , and persistent cravings lasting up to a week after taking synthetic cannabinoids, indicating that synthetic cannabinoids may be more addictive than marijuana . Studies have strongly linked particular synthetic cannabinoids with psychosis . The use of synthetic cannabinoids can be associated with psychosis and physicians are beginning to investigate if some patients with inexplicable psychotic symptoms may have at one point used synthetic cannabinoids. In contrast to most other recreational drugs ,

3920-695: The creator of the substance (e.g., JWH stands for John W. Huffman ), which can include several substances with different base structures such as classical cannabinoids and unrelated naphthoylindoles. Synthetic marijuana compounds began to be manufactured and sold in the early 2000s. From 2008 to 2014, 142 synthetic cannabinoid receptor agonists were reported to the European Monitoring-Center for Drugs and Drug Addiction (EMCDDA). Reported user negative effects include palpitations , paranoia , intense anxiety , nausea , vomiting, confusion, poor coordination, and seizures. There have also been reports of

4000-492: The difficulty of distinguishing natural cannabinoids obtained in laboratory (for example, CBD or synthetic THC ) from artificial novel synthetic cannabinoid analog compounds not present in nature (like nabilone, Spice, the HU, JWH series, etc.), the term "neocannabinoid" has been proposed to name the latter. Synthetic cannabinoids were made for cannabinoid research focusing on tetrahydrocannabinol (THC), cannabinoid receptors , and

4080-457: The dramatic psychotic state induced by use of synthetic cannabinoids has been reported, in multiple cases, to persist for several weeks, and in one case for seven months, after complete cessation of drug use. Some studies suggest that not only can synthetic cannabinoids induce psychosis, but they can worsen previously stable psychotic disorders and might trigger a chronic (long-term) psychotic disorder among vulnerable individuals such as those with

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4160-420: The drug cannot be considered safe for use by women of child-bearing age, and its use is tightly controlled when used for treating other illness. Methamphetamine is available by prescription under the brand name Desoxyn . The active component of Desoxyn is dextromethamphetamine hydrochloride . This is the right-handed isomer of methamphetamine. The left-handed isomer of methamphetamine, levomethamphetamine ,

4240-433: The greater potency, the standard doses of many synthetic cannabinoids may be less than 1 mg. Most classical, non-classical, and hybrid synthetic cannabinoids have stereospecificity (one stereoisomer is usually much more potent than the other(s)). For example, HU-210 is the (–) enantiomer of 11-OH-Δ -THC-DMH and a full agonist of the CB 1 receptor ; the (+) enantiomer of 11-OH-D -THC-DMH, known as HU-211 ,

4320-730: The grounds that it contains an active substance that affects the functions of the body, and the legality of JWH-018 is under review. JWH-018, CP 47,497 and the C6, C8, and C9 homologues of CP 47,497 have been illegal in Germany since January 22, 2009. Since November 26, 2016, about 80–90% of the substances belonging to the group of synthetic cannabinoids are illegal in Germany as the law does not cover all chemical structures. JWH-018, CP 47,497 (and its homologues), and HU-210 were all made illegal in France on February 24, 2009. From June 2010, JWH-018, along with

4400-403: The intention of making a synthetic cannabinoid prodrug , which might improve absorption and confound detection. Ester bonds are easily biodegradable through spontaneous or endogenous , nonspecific esterase hydrolysis, which has been commonly used in medicinal chemistry to make ester prodrugs. The reason for the change to the quinolone substructure is unknown, but it may have been found to be

4480-478: The macroscopic scale down to the molecular, he reckoned that the molecules had to have non-superimposable mirror images. A sample with only a single enantiomer is an enantiomerically pure or enantiopure compound. From racemic acid found in grapes; from Latin racemus , meaning a bunch of grapes . This acid, when naturally produced in grapes, is only the right-handed version of the molecule, better known as tartaric acid . In many Germanic languages racemic acid

4560-422: The most common synthetic cannabinoids found in synthetic cannabinoid blends, likely due to the fact that these molecules are easier to synthesize than classical and non-classical cannabinoids. The JWH molecules were first synthesized by John William Huffman at Clemson University in the late 1990s. The FBI concluded in a 2012 memo that as a result of the publication of J.W. Huffman's research, people searching for

4640-445: The name is formatted as LinkedGroup-TailCoreLinker. For example, in 5F-MDMB-PINACA (also known as 5F-ADB ), 5F stands for the terminal fluorine or "fluorine on carbon 5" of the pentyl chain; MDMB stands for "methyl-3,3-dimethyl butanoate", the linked group; and PINACA stands for "pentyl chain (tail) indazole (core) carboxamide (linker)". Use of the term "synthetic marijuana" to describe products containing synthetic cannabinoids

4720-436: The negative effects of 5F-AKB-48 reported by users included palpitations , paranoia , intense anxiety, and a taste like burned plastic. In addition, while there are no fatal overdose cases linked to marijuana , there are deaths linked to synthetic cannabinoids each year. The most common mechanisms leading to death following synthetic cannabinoid use include behavioral risks, such as self-harm and suicide , falling from

4800-423: The prefix rac- (or racem- ) or the symbols RS and SR (all in italic letters) are used. If the ratio is not 1:1 (or is not known), the prefix (+)/(−) , d/l - or d/l- (with a slash) is used instead. The usage of d and l is discouraged by IUPAC . A racemate is optically inactive ( achiral ), meaning that such materials do not rotate the polarization of plane- polarized light. Although

4880-479: The products tested. Other non-cannabinoid ingredients that have been found in synthetic cannabinoid blends include harmine and harmaline , reversible monoamine oxidase inhibitors , which have been found with myristicin and asarone ; substituted cathinone derived stimulant drugs such as 4-methylbuphedrone and 4'-methyl-alpha-PPP ; and psychedelic tryptamine derivatives such as 4-HO-DET . Packages of synthetic cannabinoid products can claim to contain

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4960-415: The products. For example, AKB-48 (also known as APINACA ) is also the name of a popular Japanese girl band ; 2NE1 (also known as APICA ) is also a South Korean girl band ; and XLR-11 was named after the first USA-developed liquid fuel rocket for aircraft . Now many synthetic cannabinoids are assigned names derived from their four main structural components, core, tail, linker, and linked group, where

5040-545: The rat poison brodifacoum , which is added because it is thought to extend the duration of the drugs' effects. Severe illnesses and death have resulted from this contamination. Synthetic cannabinoids reagent testing kits have recently become economical. It is often difficult to determine what is in these products without reagent testing because masking agents , such as tocopherol (or vitamin E acetate that causes vaping-associated pulmonary injury ), eugenol , and fatty acids , are added to confound identification. Just as

5120-1176: The restrictions. Synthetic cannabinoids have also been used recreationally because they are inexpensive and are typically not revealed by the standard marijuana drug tests . Unlike nabilone , the synthetic cannabinoids found being used for recreational use did not have any documented therapeutic effects . Because they activate the cannabinoid CB 1 and CB 2 receptors, many of the effects of synthetic cannabinoids are similar to those of THC. These are achieved at lower doses, because many synthetic cannabinoids are more potent than marijuana, and users are often unaware of exactly what they are getting and how potent it is. For example, Δ -THC has an EC 50 of 250 nM at CB 1 and 1157 nM at CB 2 , whereas PB-22 has an EC 50 of 5.1 nM at CB 1 and 37 nM at CB 2 . Adverse effects observed due to synthetic cannabinoid use include acute kidney injury , cardiac toxicity , seizure , stroke , tremor , hypokalemia , and rhabdomyolysis . Some negative effects of 5F-PB-22 reported by users included nausea , vomiting , confusion , poor coordination , anxiety , and seizures. Some of

5200-556: The rights from Lilly in 2004. Valeant tried and failed to get the medication approved by the FDA again in 2005 and then succeeded in 2006. In 2007, Valeant acquired the United Kingdom and European Union rights to market nabilone from Cambridge Laboratories. Nabilone was approved in Austria to treat chemotherapy -induced nausea in 2013; it was already approved in Spain for the same indication and

5280-450: The sole agent, 66.1% reported problems in the central nervous system (e.g., agitation, coma , toxic psychosis ), 17% reported cardiovascular problems (e.g., tachycardia , bradycardia ), 7.6% reported pulmonary problems (5.4% of which had respiratory depression ), and 4% reported acute kidney injury . Four postmortem cases linked to the synthetic cannabinoids 5F-PB-22 have been reviewed. The postmortem blood specimens contained

5360-463: The specific antibodies in the EMIT for marijuana do not bind to them. Also, due to their high potency , a very small dose of synthetic cannabinoids is used; moreover, synthetic cannabinoids are highly metabolized by the body, so the window to detect the parent drug (the synthetic cannabinoid itself) in blood and oral fluid is very small. Serum concentrations of synthetic cannabinoids are generally in

5440-474: The structure of a synthetic cannabinoid, such as changing an indole to indazole structure ( AM-2201 to THJ-2201 ) or terminal fluorine replacement; however, one group that was unprecedented when discovered by forensic scientists in 2013, was the quinolinyl ester synthetic cannabinoids. PB-22 and 5F-PB-22 were the first synthetic cannabinoids to include a quinoline substructure and an ester linkage . These compounds are thought to have been synthesized with

5520-767: The synthetic cannabinoid(s) used differ between each synthetic cannabinoid product sold, so do the other contents of the counterfeit product. Synthetic cannabinoids appear in many CBD brands in products such as gummy bears and vape cartridges. Synthetic cannabinoid components of 'Spice' (a non-exhaustive list): Most blends consist of synthetic cannabinoids sprayed onto inert vegetable matter, but some contain other psychoactive substances , including psychoactive herbs, e.g., wild dagga and indian warrior , and psychoactive alkaloids , e.g., betonicine, aporphine , leonurine , nuciferine , and nicotine . Some synthetic cannabinoids products have also been found to contain synthetic opioids . For example, in 2010, nine people died due to

5600-549: The synthetic cannabinoids have been found to be about 2–5 times more potent at CB 1 receptors than their un-fluorinated counterparts, as shown in table two. Synthetic cannabinoids are typically not identified by the standard marijuana drug tests including the immunoassay test ( EMIT ), GC-MS screening, and multi-target screening by LC-GC/MS because those tests only detect the presence of THC and its metabolites. Although most synthetic cannabinoids are analogs of THC, they are structurally different enough that, for example,

5680-551: The term synthetic cannabinoid is more appropriate. Nearly 700 "herbal incense" blends exist. They are often called "synthetic marijuana", "natural herbs", "herbal incense", or "herbal smoking blends" and often labeled "not for human consumption". In some Spanish-speaking countries, such as Chile and Argentina, such preparations are often referred to as cripy . According to the Psychonaut Web Mapping Research Project, synthetic cannabinoids, sold under

5760-407: The two enantiomers rotate plane-polarized light in opposite directions, the rotations cancel each other out because they are present in equal amounts of negative (-) counterclockwise ( levorotatory ) and positive (+) clockwise ( dextrorotatory ) enantiomers. In contrast to the two pure enantiomers, which have identical physical properties except for the direction of rotation of plane-polarized light,

5840-404: Was racemic acid , which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid . He manually separated the crystals of a mixture, starting from an aqueous solution of the sodium ammonium salt of racemate tartaric acid. Pasteur benefited from the fact that ammonium tartrate salt gives enantiomeric crystals with distinct crystal forms (at 77 °F). Reasoning from

5920-431: Was a racemic mixture, and isolated dextroamphetamine was later introduced to the market as Dexedrine. The prescription analgesic tramadol is also a racemate. In some cases (e.g., ibuprofen and thalidomide ), the enantiomers interconvert or racemize in vivo . This means that preparing a pure enantiomer for medication is largely pointless. However, sometimes samples containing pure enantiomers may be made and sold at

6000-471: Was determined to be a synthetic cannabinoid called AMB-FUBINACA . Since March 2018, Illinois, Wisconsin, Maryland, and 8 other states in the United States have had an outbreak of severe bleeding caused by a synthetic cannabinoid contaminated with brodifacoum , a rat poison that causes bleeding. Illinois was hit the hardest and on April 5, 2018, the CDC issued a Clinical Action alert to health care providers across

6080-658: Was evidence of safety and modest efficacy for some conditions. The main settings that have seen published clinical trials of nabilone include movement disorders such as parkinsonism , chronic pain, dystonia and spasticity neurological disorders, multiple sclerosis, and the nausea of cancer chemotherapy. Nabilone is also effective in the treatment of inflammatory bowel disease , especially ulcerative colitis . In one study of current daily users of cannabis, oral nabilone at 4, 6, and 8 mg produced sustained and dose-dependent mood elevation and psychomotor slowing comparable to 10 or 20 mg oral dronabinol (THC). Nabilone had

6160-562: Was found). No official studies have been conducted on the effects of synthetic cannabinoids on humans (as is often the case with illegal and potentially toxic compounds); however, user reports and the effects experienced by patients seeking medical care after taking synthetic cannabinoids have been published. Each of the many different synthetic cannabinoids can have different effects at different dosages. The CDC described synthetic cannabinoid overdoses between 2010 and 2015 and of 277 drug overdose patients who reported synthetic cannabinoid as

6240-552: Was identified in samples of the drug tested by the DEA . From September 21–22, 2018, almost 50 people overdosed and two people died in the Kensington area of Philadelphia . Officials believed the cause to be a combination of heroin or fentanyl and a synthetic cannabinoid. This same area in Philadelphia had 155 people overdose and 10 people die from a combination of heroin, fentanyl, and

6320-870: Was legal in Belgium to treat glaucoma , spasticity in multiple sclerosis , wasting due to AIDS , and chronic pain . Synthetic cannabinoid Typically, synthetic cannabinoids are sprayed onto plant matter and are usually smoked, although they have also been ingested as a concentrated liquid form in the United States and United Kingdom since 2016. They have been marketed as herbal incense, or "herbal smoking blends", and sold under common names like K2 , spice , and synthetic marijuana . They are often labeled "not for human consumption" for liability defense. A large and complex variety of synthetic cannabinoids are designed in an attempt to avoid legal restrictions on cannabis , making synthetic cannabinoids designer drugs . Most synthetic cannabinoids are agonists of

6400-443: Was one of the first synthetic cannabinoids being used recreationally. CP-47,497-C8 is made by extending the dimethylheptyl side chain of CP-47,497 to a dimethyloctyl side chain. It was discovered by forensic scientists in a herbal blend known as "Spice" in 2008, along with JWH-018 , an aminoalkylindole . Hybrid cannabinoids have a combination of classical and non-classical cannabinoid structural features. For example, AM-4030 ,

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