SDB-005

SDB-005
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B;
Identifiers
	IUPAC name Naphthalen-1-yl 1-pentyl-1H-indazole-3-carboxylate;
CAS Number	2180934-13-6 ;
PubChem CID	125181303;
ChemSpider	30922481;
UNII	Z6XWV5U765;
CompTox Dashboard (EPA)	DTXSID601010032 ;
Chemical and physical data
Formula	C23H22N2O2
Molar mass	358.441 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCN1N=C(C(=O)OC2=CC=CC3=C2C=CC=C3)C2=C1C=CC=C2;
	InChI InChI=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; Key:JBVNFKZVDLFOAY-UHFFFAOYSA-N;

SDB-005 (also known as NA-PINAC using systematic EUDA nomenclature)^[1] is an indazole-based synthetic cannabinoid that has been sold online as a designer drug.^[2] 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).^[3]

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.^[4] Consequently, there are now two distinct, yet fairly closely related cannabinoid compounds, which may both be referred to under the code SDB-005.

References

^ Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID 36346325.
^ "SDB-005". Cayman Chemical. Retrieved 27 June 2015.
^ Banister SD, Wilkinson SM, Longworth M, Stuart J, Apetz N, English K, et al. (July 2013). "The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse". ACS Chemical Neuroscience. 4 (7): 1081–92. doi:10.1021/cn400035r. PMC 3715837. PMID 23551277.
^ EWS_EU: Neue Psychoaktive Substanzen, April 2015

[1] Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID 36346325.

[2] "SDB-005". Cayman Chemical. Retrieved 27 June 2015.

[3] Banister SD, Wilkinson SM, Longworth M, Stuart J, Apetz N, English K, et al. (July 2013). "The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse". ACS Chemical Neuroscience. 4 (7): 1081–92. doi:10.1021/cn400035r. PMC 3715837. PMID 23551277.

[4] EWS_EU: Neue Psychoaktive Substanzen, April 2015

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See also

References