BzODZ-EPyr

BzODZ-EPyr
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name 3-(3-Benzyl-1,2,4-oxadiazol-5-yl)-1-[2-(pyrrolidin-1-yl)ethyl]-1H-indole;
PubChem CID	9842447;
ChemSpider	8018162;
UNII	WSQ49D7D2Q;
ChEMBL	ChEMBL463656;
CompTox Dashboard (EPA)	DTXSID301045812 ;
Chemical and physical data
Formula	C23H24N4O
Molar mass	372.472 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C(C1=CC=CC=C1)C2=NOC(=N2)C3=C[N](C4=CC=CC=C34)CCN5CCCC5;
	InChI InChI=1S/C23H24N4O/c1-2-8-18(9-3-1)16-22-24-23(28-25-22)20-17-27(15-14-26-12-6-7-13-26)21-11-5-4-10-19(20)21/h1-5,8-11,17H,6-7,12-16H2; Key:RUVOQWMACBDQDK-UHFFFAOYSA-N;

BzODZ-EPyr is an indole based synthetic cannabinoid that has been sold as a designer drug in Russia.^[1]

It acts as a CB₁ receptor agonist with a pK_B value of 7.2 and demonstrates that replacing the ketone in 3-carbonylindoles with an oxadiazole spacer does not generally lead to activity loss.^[2]^[3]

References

^ Shevyrin V, Melkozerov V, Eltsov O, Shafran Y, Morzherin Y (February 2016). "Synthetic cannabinoid 3-benzyl-5-[1-(2-pyrrolidin-1-ylethyl)-1H-indol-3-yl]-1,2,4-oxadiazole. The first detection in illicit market of new psychoactive substances". Forensic Science International. 259: 95–100. doi:10.1016/j.forsciint.2015.12.019. PMID 26771874.
^ Moloney GP, Angus JA, Robertson AD, Stoermer MJ, Robinson M, Wright CE, et al. (March 2008). "Synthesis and cannabinoid activity of 1-substituted-indole-3-oxadiazole derivatives: novel agonists for the CB1 receptor". European Journal of Medicinal Chemistry. 43 (3): 513–39. doi:10.1016/j.ejmech.2007.04.007. PMID 17582659.
^ US 6930118, Moloney PG, Robertson AD, "3-Oxadiazol-5-yl-1-aminoalkyl-1h-indole derivatives", issued 2005, assigned to Amrad Operations Pty. Ltd.

This cannabinoid related article is a stub. You can help Wikipedia by expanding it.

[1] Shevyrin V, Melkozerov V, Eltsov O, Shafran Y, Morzherin Y (February 2016). "Synthetic cannabinoid 3-benzyl-5-[1-(2-pyrrolidin-1-ylethyl)-1H-indol-3-yl]-1,2,4-oxadiazole. The first detection in illicit market of new psychoactive substances". Forensic Science International. 259: 95–100. doi:10.1016/j.forsciint.2015.12.019. PMID 26771874.

[2] Moloney GP, Angus JA, Robertson AD, Stoermer MJ, Robinson M, Wright CE, et al. (March 2008). "Synthesis and cannabinoid activity of 1-substituted-indole-3-oxadiazole derivatives: novel agonists for the CB1 receptor". European Journal of Medicinal Chemistry. 43 (3): 513–39. doi:10.1016/j.ejmech.2007.04.007. PMID 17582659.

[3] US 6930118, Moloney PG, Robertson AD, "3-Oxadiazol-5-yl-1-aminoalkyl-1h-indole derivatives", issued 2005, assigned to Amrad Operations Pty. Ltd.

[1]

[2]

[3]

Legal status

Legal status	CA: Schedule II DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act
Identifiers
IUPAC name 3-(3-Benzyl-1,2,4-oxadiazol-5-yl)-1-[2-(pyrrolidin-1-yl)ethyl]-1H-indole
PubChem CID	9842447
ChemSpider	8018162
UNII	WSQ49D7D2Q
ChEMBL	ChEMBL463656
CompTox Dashboard (EPA)	DTXSID301045812
Chemical and physical data
Formula	C₂₃H₂₄N₄O
Molar mass	372.472 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C(C1=CC=CC=C1)C2=NOC(=N2)C3=C[N](C4=CC=CC=C34)CCN5CCCC5
InChI InChI=1S/C23H24N4O/c1-2-8-18(9-3-1)16-22-24-23(28-25-22)20-17-27(15-14-26-12-6-7-13-26)21-11-5-4-10-19(20)21/h1-5,8-11,17H,6-7,12-16H2 Key:RUVOQWMACBDQDK-UHFFFAOYSA-N

BzODZ-EPyr

See also

References