ADB-P7AICA

Last updated
ADB-P7AICA
ADB-P7AICA structure.png
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
Identifiers
  • N-[(2S)-1-amino-3,3-dimethyl-1-oxobutan-2-yl]-1-pentylpyrrolo[2,3-b]pyridine-3-carboxamide
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
Formula C19H28N4O2
Molar mass 344.459 g·mol−1
3D model (JSmol)
  • NC(=O)[C@@H](NC(=O)c1cn(CCCCC)c2ncccc21)C(C)(C)C
  • InChI=1S/C19H28N4O2/c1-5-6-7-11-23-12-14(13-9-8-10-21-17(13)23)18(25)22-15(16(20)24)19(2,3)4/h8-10,12,15H,5-7,11H2,1-4H3,(H2,20,24)(H,22,25)/t15-/m1/s1
  • Key:QDZHLYBDQFZWCJ-OAHLLOKOSA-N

ADB-P7AICA is a cannabinoid designer drug that has been found as an ingredient in some synthetic cannabis products, first identified by the DEA in early 2021. [1] [2]

See also

Related Research Articles

<span class="mw-page-title-main">ADBICA</span> Group of stereoisomers

ADBICA (also known as ADB-PICA) is a designer drug identified in synthetic cannabis blends in Japan in 2013. ADBICA had not previously been reported in the scientific literature prior to its sale as a component of synthetic cannabis blends. ADBICA features a carboxamide group at the 3-indole position, like SDB-001 and STS-135. The stereochemistry of the tert-butyl side-chain in the product is unresolved, though in a large series of indazole derivatives structurally similar to ADBICA that are disclosed in Pfizer patent WO 2009/106980, activity resides exclusively in the (S) enantiomers. ADBICA is a potent agonist of the CB1 receptor and CB2 receptor with an EC50 value of 0.69 nM and 1.8 nM respectively.

<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">ADB-PINACA</span> Chemical compound

ADB-PINACA is a cannabinoid designer drug that is an ingredient in some synthetic cannabis products. It is a potent agonist of the CB1 receptor and CB2 receptor with EC50 values of 0.52 nM and 0.88 nM respectively. Like MDMB-FUBINACA, this compound incorporates the unnatural amino acid tert-leucine.

<span class="mw-page-title-main">NM-2201</span> Chemical compound

NM-2201 (also known as CBL-2201 and NA-5F-PIC) is an indole-based synthetic cannabinoid that presumably has similar properties to the closely related 5F-PB-22 and NNE1, which are both full agonists and unselectively bind to CB1 and CB2 receptors with low nanomolar affinity.

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

APP-FUBINACA is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. Pharmacological testing showed APP-FUBINACA to have only moderate affinity for the CB1 receptor, with a Ki of 708 nM, while its EC50 was not tested. It contains a phenylalanine amino acid residue in its structure.

<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 should not be confused with the amantadine analogue 4F-ABINACA. 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">CUMYL-CBMICA</span> Chemical compound

CUMYL-CBMICA (SGT-280) is an indole-3-carboxamide based synthetic cannabinoid receptor agonist which has been sold as a designer drug, first being identified in Germany in August 2019. Since the structure fell outside the German drug analogue law provisions at the time, an amendment was made to the law to expand the relevant definition, which came into effect in April 2020. It has been shown to act as a CB1 receptor agonist with an EC50 of 62.9nM.

<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-HEXINACA</span> Chemical compound

ADB-HEXINACA 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 longer chain homologue of previously encountered synthetic cannabinoid compounds such as ADB-BUTINACA and ADB-PINACA. The pharmacology of ADB-HEXINACA and numerous analogues at CB1 and CB2 receptors has been reported.

<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">MDMB-5Br-INACA</span> Chemical compound

MDMB-5Br-INACA is an indazole-3-carboxamide derivative which has been sold as a designer drug. 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.

<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">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. "Announcement of a Newly Identified Synthetic Cannabinoid ADB-P7AICA" (PDF). Drug Enforcement Administration Toxicology Testing Program. U.S. Department of Justice. 22 February 2021.
  2. Sparkes E, Cairns EA, Kevin RC, Lai F, Grafinger KE, Chen S, et al. (February 2022). "Structure-activity relationships of valine, tert-leucine, and phenylalanine amino acid-derived synthetic cannabinoid receptor agonists related to ADB-BUTINACA, APP-BUTINACA, and ADB-P7AICA". RSC Medicinal Chemistry. 13 (2): 156–174. doi:10.1039/d1md00242b. PMC   8864554 . PMID   35308023.