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| Chemical and physical data | |
| Formula | C15H18BrN3O3 |
| Molar mass | 368.231 g·mol−1 |
| 3D model (JSmol) | |
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MDMB-5Br-INACA is an indazole-3-carboxamide derivative which has been sold as a designer drug. [2] Surprisingly it appears to produce psychoactive activity despite the lack of a "tail" group at the indazole 1-position, but is of relatively low potency and has been encountered being misrepresented as other illicit drugs such as MDMA. [3] [4]
MDMB-5Br-INACA is believed to be used as a precursor in the synthesis of synthetic cannabinoids. It has been sold online as "half finished" synthetic cannabinoids, sometimes as a "chemistry kit" with other compounds required to complete the reaction. This reaction would complete MDMB-5Br-INACA by giving it a "tail" group required for high cannabinoid activity. Other precursors lacking a tail chain have also been marketed such as (ADB-5-Br-INACA), [5] (CH-IATA), (ADB-IACA), and (ADB-5’Br-EZO-CA). This may be due to increasing legality changes worldwide on synthetic cannabinoids. [6] [7]
In the United States, MDMB-5Br-INACA is unscheduled at the federal level as of May 22nd, 2023.
North Dakota has placed MDMB-5Br-INACA (along with ADB-5'Br-BINACA, ADB-5'Br-BUTINACA and ADB-5-Br-INACA) into Schedule I on 04/27/2023. [8]
ADB-FUBINACA (ADMB-FUBINACA) is a designer drug identified in synthetic cannabis blends in Japan in 2013. In 2018, it was the third-most common synthetic cannabinoid identified in drugs seized by the Drug Enforcement Administration.
AB-CHMINACA is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor (Ki = 0.78 nM) and CB2 receptor (Ki = 0.45 nM) and fully substitutes for Δ9-THC in rat discrimination studies, while being 16x more potent. Continuing the trend seen in other cannabinoids of this generation, such as AB-FUBINACA and AB-PINACA, it contains a valine amino acid amide residue as part of its structure, where older cannabinoids contained a naphthyl or adamantane residue.
5F-ADB (also known as MDMB-5F-PINACA and 5F-MDMB-PINACA) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family, which has been used as an active ingredient in synthetic cannabis products and has been sold online as a designer drug. 5F-ADB is a potent agonist of the CB1 receptor, though it is unclear whether it is selective for this target. 5F-ADB was first identified in November 2014 from post-mortem samples taken from an individual who had died after using a product containing this substance. Subsequent testing identified 5F-ADB to have been present in a total of ten people who had died from unexplained drug overdoses in Japan between September 2014 and December 2014. 5F-ADB is believed to be extremely potent based on the very low levels detected in tissue samples, and appears to be significantly more toxic than earlier synthetic cannabinoid drugs that had previously been sold.
ADB-CHMINACA (also known as ADMB-CHMINACA and MAB-CHMINACA) is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor with a binding affinity of Ki = 0.289 nM and was originally developed by Pfizer in 2009 as an analgesic medication. It was identified in cannabinoid blends in Japan in early 2015.
5F-APINACA is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. Structurally it closely resembles cannabinoid compounds from patent WO 2003/035005 but with a 5-fluoropentyl chain on the indazole 1-position, and 5F-APINACA falls within the claims of this patent, as despite not being disclosed as an example, it is very similar to the corresponding pentanenitrile and 4-chlorobutyl compounds which are claimed as examples 3 and 4.
MDMB-FUBINACA (also known as MDMB(N)-Bz-F and FUB-MDMB) is an indazole-based synthetic cannabinoid that is a potent agonist for the cannabinoid receptors, with Ki values of 1.14 nM at CB1 and 0.1228 nM at CB2 and EC50 values of 0.2668 nM at CB1 and 0.1411 nM at CB2, and has been sold online as a designer drug. Its benzyl analogue (instead of 4-fluorobenzyl) has been reported to be a potent agonist for the CB1 receptor (Ki = 0.14 nM, EC50 = 2.42 nM). The structure of MDMB-FUBINACA contains the amino acid, 3-methylvaline or tert-leucine methyl ester.
MDMB-CHMINACA (also known as MDMB(N)-CHM) is an indazole-based synthetic cannabinoid that acts as a potent agonist of the CB1 receptor, and has been sold online as a designer drug. It was invented by Pfizer in 2008, and is one of the most potent cannabinoid agonists known, with a binding affinity of 0.0944 nM at CB1, and an EC50 of 0.330 nM. It is closely related to MDMB-FUBINACA, which caused at least 1000 hospitalizations and 40 deaths in Russia as consequence of intoxication.
5F-AB-FUPPYCA (also known as AZ-037) is a pyrazole-based synthetic cannabinoid that is presumed to be an agonist of the CB1 receptor and has been sold online as a designer drug. It was first detected by the EMCDDA as part of a seizure of 540 g white powder in France in February 2015.
CUMYL-4CN-BINACA (also known as CUMYL-CYBINACA or SGT-78) is an indazole-3-carboxamide based synthetic cannabinoid that has been sold online as a designer drug. It is a potent agonist for cannabinoid receptors CB1 and CB2, with in vitro EC50 values of 0.58 nM and 6.12 nM, respectively. In mice, CUMYL-4CN-BINACA produces hypothermic and pro-convulsant effects via the CB1 receptor, and anecdotal reports suggest it has an active dose of around 0.1 mg in humans.
5F-CUMYL-P7AICA is a pyrrolo[2,3-b]pyridine-3-carboxamide based synthetic cannabinoid that has been sold as a designer drug. It was first identified by the EMCDDA in February 2015.
MDMB-4en-PINACA is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. MDMB-4en-PINACA was first identified in Europe in 2017. In 2021, MDMB-4en-PINACA was the most common synthetic cannabinoid identified by the Drug Enforcement Administration in the United States. MDMB-4en-PINACA differs from 5F-MDMB-PINACA due to replacement of 5-fluoropentyl with a pent-4-ene moiety (4-en).
4F-MDMB-BINACA (also known as MDMB-4F-BINACA, 4F-MDMB-BUTINACA or 4F-ADB) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family. It has been used as an active ingredient in synthetic cannabis products and sold as a designer drug since late 2018. 4F-MDMB-BINACA is an agonist of the CB1 receptor (EC50 = 7.39 nM), though it is unclear whether it is selective for this target. In December 2019, the UNODC announced scheduling recommendations placing 4F-MDMB-BINACA into Schedule II throughout the world.
ADB-BINACA (also known as ADMB-BZINACA using EMCDDA naming standards) is a cannabinoid designer drug that has been found as an ingredient in some synthetic cannabis products. It was originally developed by Pfizer as a potential analgesic, and is a potent agonist of the CB1 receptor with a binding affinity (Ki) of 0.33 nM and an EC50 of 14.7 nM.
ADB-BUTINACA (also known as ADMB-BINACA using EMCDDA naming standards) is a synthetic cannabinoid compound which has been sold as a designer drug. It is a potent CB1 agonist, with a binding affinity of 0.29nM for CB1 and 0.91nM for CB2, and an EC50 of 6.36 nM for CB1.
ADB-4en-PINACA is a cannabinoid designer drug that has been found as an ingredient in some synthetic cannabis products, first appearing in early 2021. It is a reasonably potent cannabinoid agonist in vitro but has not been so widely sold as related compounds such as ADB-PINACA and MDMB-4en-PINACA.
ADB-FUBIATA (AD-18, FUB-ACADB, ADB-FUBIACA) is a synthetic cannabinoid compound first identified in 2021. It is closely related in structure to the older compound ADB-FUBICA but with the amide linker group extended by the addition of a methylene bridge. It started to be sold as an ingedient in grey-market synthetic cannabis blends following the introduction of legislation in China which for the first time introduced general controls on various classes of synthetic cannabinoids, but did not encompass compounds where the linker group had been extended in this fashion. ADB-FUBIATA has many times lower affinity for cannabinoid receptors than ADB-FUBICA with an EC50 of only 635 nM at CB1, but retains full agonist activity at this target, while being practically inactive at CB2.
ADB-5'Br-PINACA (5'-Br-ADB-PINACA) is an indazole-3-carboxamide based synthetic cannabinoid receptor agonist that has been sold as a designer drug. It was first identified in Abu Dhabi in September 2022, but has subsequently been found in the US and Europe. While formal pharmacology studies have not yet been carried out, ADB-5'Br-PINACA is believed to be a highly potent synthetic cannabinoid with similar potency to compounds such as MDMB-FUBINACA and 5F-ADB which have been responsible for numerous fatal and non-fatal drug overdoses, consistent with previously reported compounds from the patent literature showing bromination of the indazole ring at the 5-, 6- or 7- positions to increase potency over the unsubstituted analogues. ADB-5'Br-PINACA is the 5'-bromo analog of ADB-PINACA.
MDMB-5'Br-BUTINACA (5'-Br-MDMB-BUTINACA) is an indazole-3-carboxamide based synthetic cannabinoid receptor agonist that has been sold as a designer drug. It was first identified in Russia in August 2022. It is believed to be synthesized from the "half finished" synthesis precursor MDMB-5Br-INACA, which is shipped to the destination and then the final synthetic step is completed on arrival.
ADB-5'F-BUTINACA is an indazole-3-carboxamide based synthetic cannabinoid receptor agonist. It was synthesised as part of investigations into related compounds such as ADB-5'Br-BUTINACA and MDMB-5'Br-BUTINACA, and confirmed that fluorination of the indazole 5-position increases potency in a similar manner to bromination.
ADB-5'Br-BUTINACA (ADB-B-5Br-INACA) is an indazole-3-carboxamide based synthetic cannabinoid receptor agonist which has been sold as a designer drug, first detected in Philadelphia in the US in May 2022, and subsequently found in South Korea, Portugal and Sweden. It is specifically listed as an illegal drug in Italy, South Korea and several states in the US, and controlled under analogue legislation in various other jurisdictions.
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