SDB-005

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = Naphthalen-1-yl 1-pentyl-1H-indazole-3-carboxylate

| image = SDB-005_structure.png

| image_class = skin-invert-image

| width = 180

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| pregnancy_AU =

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| legal_AU =

| legal_CA = Schedule II

| legal_DE = NpSG

| legal_UK = Class B

| legal_US =

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| routes_of_administration =

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 2180934-13-6

| ATC_prefix =

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| PubChem = 125181303

| ChemSpiderID = 30922481

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Z6XWV5U765

| smiles = CCCCCN1N=C(C(=O)OC2=CC=CC3=C2C=CC=C3)C2=C1C=CC=C2

| StdInChI = 1S/C23H22N2O2/c1-2-3-8-16-25-20-14-7-6-13-19(20)22(24-25)23(26)27-21-15-9-11-17-10-4-5-12-18(17)21/h4-7,9-15H,2-3,8,16H2,1H3

| StdInChIKey = JBVNFKZVDLFOAY-UHFFFAOYSA-N

| C=23 | H=22 | N=2 | O=2

}}

SDB-005 (also known as NA-PINAC using systematic EUDA nomenclature){{cite journal |vauthors=Pulver B, Fischmann S, Gallegos A, Christie R |date=March 2023 |title=EMCDDA framework and practical guidance for naming synthetic cannabinoids |url=https://www.euda.europa.eu/drugs-library/emcdda-framework-and-practical-guidance-naming-synthetic-cannabinoids_en |journal=Drug Testing and Analysis |volume=15 |issue=3 |pages=255–276 |doi=10.1002/dta.3403 |pmid=36346325|url-access=subscription }} is an indazole-based synthetic cannabinoid that has been sold online as a designer drug.{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/15389 | title=SDB-005 | publisher=Cayman Chemical | access-date=27 June 2015}} It is presumed to be an agonist of the CB₁ and CB₂ cannabinoid receptors. SDB-005 is the indazole core analog of PB-22 where the 8-hydroxyquinoline has also been replaced with a naphthalene group.

The code number SDB-005 was originally used for a different compound, the N-phenyl instead of N-benzyl analogue of SDB-006. This compound is a potent agonist of the CB₁ receptor (K_i = 21 nM) and CB₂ receptor (K_i = 140 nM).{{cite journal | vauthors = Banister SD, Wilkinson SM, Longworth M, Stuart J, Apetz N, English K, Brooker L, Goebel C, Hibbs DE, Glass M, Connor M, McGregor IS, Kassiou M | display-authors = 6 | title = The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse | journal = ACS Chemical Neuroscience | volume = 4 | issue = 7 | pages = 1081–92 | date = July 2013 | pmid = 23551277 | pmc = 3715837 | doi = 10.1021/cn400035r }}

Image:originalSDB005_structure.png{{clear left}}

However, SDB-005 was subsequently used as the name for the indazole-3-carboxylate compound mentioned above when it was sold in Europe as a designer drug, and was entered into the EMCDDA synthetic drug database under this name.[https://forum.goeg.at/EwsForum/default.aspx?g=posts&t=205 EWS_EU: Neue Psychoaktive Substanzen, April 2015] Consequently, there are now two distinct, yet fairly closely related cannabinoid compounds, which may both be referred to under the code SDB-005.