MDMB-5Br-INACA

Last updated

MDMB-5Br-INACA
MDMB-5Br-INACA structure.png
Legal status
Legal status
Identifiers
  • methyl (2S)-2-[(5-bromo-1H-indazole-3-carbonyl)amino]-3,3-dimethylbutanoate
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C15H18BrN3O3
Molar mass 368.231 g·mol−1
3D model (JSmol)
  • O=C(OC)[C@@H](NC(=O)c1n[NH]c2ccc(Br)cc21)C(C)(C)C
  • InChI=1S/C15H18BrN3O3/c1-15(2,3)12(14(21)22-4)17-13(20)11-9-7-8(16)5-6-10(9)18-19-11/h5-7,12H,1-4H3,(H,17,20)(H,18,19)/t12-/m1/s1
  • Key:QGEVEXPJOKFMAN-GFCCVEGCSA-N

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]

Contents

Use as a precursor

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]

Legality

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]

See also

Related Research Articles

<span class="mw-page-title-main">AB-FUBINACA</span> Chemical compound

AB-FUBINACA (AMB-FUBINACA) is a psychoactive drug that acts as a potent agonist for the cannabinoid receptors, with Ki values of 0.9 nM at CB1 and 23.2 nM at CB2 and EC50 values of 1.8 nM at CB1 and 3.2 nM at CB2. It was originally developed by Pfizer in 2009 as an analgesic medication but was never pursued for human use. In 2012, it was discovered as an ingredient in synthetic cannabinoid blends in Japan, along with a related compound AB-PINACA, which had not previously been reported.

<span class="mw-page-title-main">ADB-FUBINACA</span> Chemical compound

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.

<span class="mw-page-title-main">AB-CHMINACA</span> Chemical compound

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.

<span class="mw-page-title-main">5F-ADB</span> Chemical compound

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.

<span class="mw-page-title-main">ADB-CHMINACA</span> Chemical compound

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.

<span class="mw-page-title-main">5F-APINACA</span> Chemical compound

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.

<span class="mw-page-title-main">5F-AB-FUPPYCA</span> Chemical compound

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.

<span class="mw-page-title-main">CUMYL-4CN-BINACA</span> Chemical compound

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.

<span class="mw-page-title-main">5F-CUMYL-P7AICA</span> Chemical compound

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.

<span class="mw-page-title-main">MDMB-4en-PINACA</span> Chemical compound

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).

<span class="mw-page-title-main">4F-MDMB-BINACA</span> Chemical compound

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.

<span class="mw-page-title-main">ADB-BINACA</span> Chemical compound

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.

<span class="mw-page-title-main">ADB-BUTINACA</span> Chemical compound

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.

<span class="mw-page-title-main">ADB-4en-PINACA</span> Chemical compound

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.

<span class="mw-page-title-main">ADB-FUBIATA</span> Chemical compound

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.

<span class="mw-page-title-main">ADB-5'Br-PINACA</span> Synthetic cannabinoid, designer drug

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.

<span class="mw-page-title-main">MDMB-5'Br-BUTINACA</span> Chemical compound

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.

<span class="mw-page-title-main">ADB-5'F-BUTINACA</span> Chemical compound

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.

<span class="mw-page-title-main">ADB-5'Br-BUTINACA</span> Chemical compound

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.

<span class="mw-page-title-main">MDMB-BINACA</span> Chemical compound

MDMB-BINACA (MDMB-BUTINACA) is an indazole-3-carboxamide based synthetic cannabinoid receptor agonist that has been sold as a designer drug, first identified in Sweden in May 2023. It has a similar chemical structure to potent cannabinoid agonists previously reported such as ADB-BUTINACA and MDMB-5'Br-BUTINACA, and is believed to have similar effects.

References

  1. ↑ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ↑ "CFSRE Analysis Report" (PDF). Indianapolis-Marion County Forensic Services Agency. 17 May 2022.
  3. ↑ "Drug testers warn of new synthetic cannabinoid being sold as MDMA". New Zealand Herald. 5 August 2022.
  4. ↑ Deventer MH, Persson M, Norman C, Liu H, Connolly MJ, Daéid NN, et al. (October 2023). "In vitro cannabinoid activity profiling of generic ban-evading brominated synthetic cannabinoid receptor agonists and their analogs". Drug Testing and Analysis. doi:10.1002/dta.3592. PMID   37903509. S2CID   264671035.
  5. ↑ Choi H, Kim S, Jang H, Kim HJ, Choe S (September 2022). "Identification of a novel bromoindazole synthetic cannabinoid analogue in seized e-cigarette liquid: ADB-BRINACA". Forensic Science International. 338: 111385. doi:10.1016/j.forsciint.2022.111385. PMID   35863161.
  6. ↑ "Cumyl-PeGaClone and other recently encountered synthetic cannabinoid receptor agonists. A review of the evidence on their use and harms" (PDF). Advisory Council on the Misuse of Drugs. 2022.
  7. ↑ Andrews R, Jorge R, Christie R, Gallegos A (April 2023). "From JWH-018 to OXIZIDS: Structural evolution of synthetic cannabinoids in the European Union from 2008 to present day". Drug Testing and Analysis. 15 (4): 378–387. doi:10.1002/dta.3422. PMID   36507715.
  8. ↑ "AN ACT to amend and reenact sections 19-03.1-05, 19-03.1-11, and 19-03.1-13 of the North Dakota Century Code, relating to the scheduling of controlled substances; and to declare an emergency" (PDF). Sixty-eighth Legislative Assembly of North Dakota in Regular Session. 3 January 2023.
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