Adamantyl-THPINACA

Adamantyl-THPINACA
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B;
Identifiers
	IUPAC name N-(2-Adamantyl)-1-(tetrahydropyran-4-ylmethyl)indazole-3-carboxamide;
CAS Number	2365471-86-7 ; 1400742-48-4 (1-adamantyl isomer);
PubChem CID	123132009;
ChemSpider	58858889;
UNII	7I4LAF1R3Y;
CompTox Dashboard (EPA)	DTXSID101009995 ;
Chemical and physical data
Formula	C24H31N3O2
Molar mass	393.531 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C12C(C3CC(CC(C1)C3)C2)NC(=O)C2=NN(C3=CC=CC=C23)CC2CCOCC2;
	InChI InChI=1/C24H31N3O2/c28-24(25-22-18-10-16-9-17(12-18)13-19(22)11-16)23-20-3-1-2-4-21(20)27(26-23)14-15-5-7-29-8-6-15/h1-4,15-19,22H,5-14H2,(H,25,28)/f/h25H; Key:XFZLBNDGZVRJNJ-UHFFFAOYSA-N;

Adamantyl-THPINACA (ATHPINACA, AD-THPINACA)^[1] is an indazole-based synthetic cannabinoid,^[2] which was first reported to Europol in Slovenia in January 2015.^[3] It is known as both the 1-adamantyl and 2-adamantyl isomers (SGT-40 and SGT-194 respectively), which can be distinguished by GC-EI-MS.^[4] It is banned in Sweden^[5] and Russia.^[6] Both the 1-adamantyl and 2-adamantyl isomers are specifically listed as illegal drugs in Japan.^[7] Given the known metabolic liberation (and presence as an impurity) of amantadine in the related compound APINACA, it is suspected that metabolic hydrolysis of the amide group of Adamantyl-THPINACA may also release amantadine.

References

^ "ATHPINACA isomer 1 (CAS 1400742-48-4)". Caymen Chemical. Retrieved 29 April 2017.
^ "Muuntohuumeiden esiintyvyys 2015" (PDF). Finnish Medicines Agency. 7 May 2015. Retrieved 10 March 2021.
^ Europol 2015 Annual Report on the implementation of Council Decision 2005/387/JHA
^ Asada A, Doi T, Tagami T, Takeda A, Sawabe Y (March 2017). "Isomeric discrimination of synthetic cannabinoids by GC-EI-MS: 1-adamantyl and 2-adamantyl isomers of N-adamantyl carboxamides". Drug Testing and Analysis. 9 (3): 378–388. doi:10.1002/dta.2124. PMID 27770510.
^ "Fler ämnen föreslås bli klassade som narkotika eller hälsofarlig vara". Folkhälsomyndigheten. Retrieved 24 July 2015.
^ List of substances prohibited in the Russian Federation
^ 指定薬物一覧

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[1] "ATHPINACA isomer 1 (CAS 1400742-48-4)". Caymen Chemical. Retrieved 29 April 2017.

[2] "Muuntohuumeiden esiintyvyys 2015" (PDF). Finnish Medicines Agency. 7 May 2015. Retrieved 10 March 2021.

[3] Europol 2015 Annual Report on the implementation of Council Decision 2005/387/JHA

[4] Asada A, Doi T, Tagami T, Takeda A, Sawabe Y (March 2017). "Isomeric discrimination of synthetic cannabinoids by GC-EI-MS: 1-adamantyl and 2-adamantyl isomers of N-adamantyl carboxamides". Drug Testing and Analysis. 9 (3): 378–388. doi:10.1002/dta.2124. PMID 27770510.

[5] "Fler ämnen föreslås bli klassade som narkotika eller hälsofarlig vara". Folkhälsomyndigheten. Retrieved 24 July 2015.

[6] List of substances prohibited in the Russian Federation

[7] 指定薬物一覧

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Legal status

Legal status	CA: Schedule II DE: NpSG (Industrial and scientific use only) UK: Class B
Identifiers
IUPAC name N-(2-Adamantyl)-1-(tetrahydropyran-4-ylmethyl)indazole-3-carboxamide
CAS Number	2365471-86-7^Y 1400742-48-4 (1-adamantyl isomer)
PubChem CID	123132009
ChemSpider	58858889
UNII	7I4LAF1R3Y
CompTox Dashboard (EPA)	DTXSID101009995
Chemical and physical data
Formula	C₂₄H₃₁N₃O₂
Molar mass	393.531 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C12C(C3CC(CC(C1)C3)C2)NC(=O)C2=NN(C3=CC=CC=C23)CC2CCOCC2
InChI InChI=1/C24H31N3O2/c28-24(25-22-18-10-16-9-17(12-18)13-19(22)11-16)23-20-3-1-2-4-21(20)27(26-23)14-15-5-7-29-8-6-15/h1-4,15-19,22H,5-14H2,(H,25,28)/f/h25H Key:XFZLBNDGZVRJNJ-UHFFFAOYSA-N

Adamantyl-THPINACA

See also

References