{{Short description|Chemical compound}} {{Drugbox | IUPAC_name = Naphthalen-1-yl 1-pentyl-1''H''-indazole-3-carboxylate | image = SDB-005_structure.png | image_class = skin-invert-image | width = 180
<!--Clinical data--> | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = Schedule II | legal_DE = NpSG | legal_UK = Class B | legal_US = | legal_status = | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 2180934-13-6 | ATC_prefix = | ATC_suffix = | 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
<!--Chemical data--> | C=23 | H=22 | N=2 | O=2 }}
'''SDB-005''' (also known as '''NA-PINAC''' using systematic EUDA nomenclature)<ref>{{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 }}</ref> is an indazole-based synthetic cannabinoid that has been sold online as a designer drug.<ref>{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/15389 | title=SDB-005 | publisher=Cayman Chemical | access-date=27 June 2015}}</ref> It is presumed to be an agonist of the CB<sub>1</sub> and CB<sub>2</sub> 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 CB<sub>1</sub> receptor (K<sub>i</sub> = 21 nM) and CB<sub>2</sub> receptor (K<sub>i</sub> = 140 nM).<ref>{{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 }}</ref>
class=skin-invert-image|200px|thumb|left|Original, non designer drug SDB-005{{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.<ref>[https://forum.goeg.at/EwsForum/default.aspx?g=posts&t=205 EWS_EU: Neue Psychoaktive Substanzen, April 2015]</ref> Consequently, there are now two distinct, yet fairly closely related cannabinoid compounds, which may both be referred to under the code SDB-005.
== See also == * 5F-PB-22 * AM-2201 * BB-22 * JWH-018 * NM-2201 * NNE1
== References == {{Reflist}}
{{Cannabinoids}} {{Cannabinoidergics}}
Category:Indazoles Category:Cannabinoids Category:Designer drugs