BTMPS

BTMPS
Names
	Other names Bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate
Identifiers
CAS Number	52829-07-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	144046 ;
ECHA InfoCard	100.052.899
EC Number	258-207-9;
MeSH	C083752
PubChem CID	164282;
UNII	6803A71201 ;
CompTox Dashboard (EPA)	DTXSID0028030 ;
	InChI InChI=1S/C28H52N2O4/c1-25(2)17-21(18-26(3,4)29-25)33-23(31)15-13-11-9-10-12-14-16-24(32)34-22-19-27(5,6)30-28(7,8)20-22/h21-22,29-30H,9-20H2,1-8H3 Key: XITRBUPOXXBIJN-UHFFFAOYSA-N;
	SMILES CC1(C)CC(CC(C)(C)N1)OC(=O)CCCCCCCCC(=O)OC2CC(C)(C)NC(C)(C)C2;
Properties
Chemical formula	C28H52N2O4
Molar mass	480.734 g·mol−1
Density	1.05 g/cm3
Melting point	81 to 85 °C (178 to 185 °F; 354 to 358 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

BTMPS (also known as Tinuvin 770) is a hindered amine light stabilizer with the chemical formula C₂₈H₅₂N₂O₄. It is a white crystalline powder.^[1]

In 2024 it was detected as an adulterant in illicitly sold fentanyl in the United States.^[2]^[3]

Production and reactions

Its production involves sebacic acid and tetramethylpiperidinol.^[4]

Potential medical significance

It is capable of inhibiting nicotinic acetylcholine receptors.^[5] Additionally, it is a potent blocker of L-type calcium channels.^[6]^[7] It is also able to induce dose-dependent hemodynamic alterations.^[8] Similar to early calcium channel blockers, it can precipitate adrenergic release.^[9]

References

^ "Bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate". pubchem.ncbi.nlm.nih.gov.
^ "BTMPS". The Center for Forensic Science Research & Education.
^ Alpert Reyes, Emily (16 September 2024). "An industrial chemical is showing up in fentanyl in the U.S., troubling scientists". Los Angeles Times. Archived from the original on 16 September 2024.
^ "Preparation method of hindered amine light stabilizer 770". 13 August 2014.
^ Papke, RL; Craig, AG; Heinemann, SF (February 1994). "Inhibition of nicotinic acetylcholine receptors by bis (2,2,6,6-tetramethyl- 4-piperidinyl) sebacate (Tinuvin 770), an additive to medical plastics". The Journal of Pharmacology and Experimental Therapeutics. 268 (2): 718–26. PMID 8113983.
^ Glossmann, H; Hering, S; Savchenko, A; Berger, W; Friedrich, K; Garcia, ML; Goetz, MA; Liesch, JM; Zink, DL; Kaczorowski, GJ (15 October 1993). "A light stabilizer (Tinuvin 770) that elutes from polypropylene plastic tubes is a potent L-type Ca(2+)-channel blocker". Proceedings of the National Academy of Sciences of the United States of America. 90 (20): 9523–7. doi:10.1073/pnas.90.20.9523. PMC 47601. PMID 8415734.
^ Sótonyi, P; Keller, E; Járay, J; Nemes, B; Benkõ, T; Kovács, A; Tolokán, A; Rajs, I (15 July 2001). "A light stabilizer Tinuvin 770-induced toxic injury of adult rat cardiac myocytes". Forensic Science International. 119 (3): 322–7. doi:10.1016/s0379-0738(00)00462-x. PMID 11390147.
^ Krepuska, M; Hubay, M; Zima, E; Kovacs, A; Kekesi, V; Kalasz, H; Szilagyi, B; Merkely, B; Sotonyi, P (2018). "Hemodynamic Effects of the Light Stabilizer Tinuvin 770 in Dogs In Vivo". The Open Medicinal Chemistry Journal. 12: 88–97. doi:10.2174/1874104501812010088. PMC 6142673. PMID 30288180.
^ Sótonyi, P; Merkely, B; Hubay, M; Járay, J; Zima, E; Soós, P; Kovács, A; Szentmáriay, I (February 2004). "Comparative study on cardiotoxic effect of Tinuvin 770: a light stabilizer of medical plastics in rat model". Toxicological Sciences. 77 (2): 368–74. doi:10.1093/toxsci/kfh025. PMID 14657520.

[1] "Bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate". pubchem.ncbi.nlm.nih.gov.

[2] "BTMPS". The Center for Forensic Science Research & Education.

[3] Alpert Reyes, Emily (16 September 2024). "An industrial chemical is showing up in fentanyl in the U.S., troubling scientists". Los Angeles Times. Archived from the original on 16 September 2024.

[4] "Preparation method of hindered amine light stabilizer 770". 13 August 2014.

[5] Papke, RL; Craig, AG; Heinemann, SF (February 1994). "Inhibition of nicotinic acetylcholine receptors by bis (2,2,6,6-tetramethyl- 4-piperidinyl) sebacate (Tinuvin 770), an additive to medical plastics". The Journal of Pharmacology and Experimental Therapeutics. 268 (2): 718–26. PMID 8113983.

[6] Glossmann, H; Hering, S; Savchenko, A; Berger, W; Friedrich, K; Garcia, ML; Goetz, MA; Liesch, JM; Zink, DL; Kaczorowski, GJ (15 October 1993). "A light stabilizer (Tinuvin 770) that elutes from polypropylene plastic tubes is a potent L-type Ca(2+)-channel blocker". Proceedings of the National Academy of Sciences of the United States of America. 90 (20): 9523–7. doi:10.1073/pnas.90.20.9523. PMC 47601. PMID 8415734.

[7] Sótonyi, P; Keller, E; Járay, J; Nemes, B; Benkõ, T; Kovács, A; Tolokán, A; Rajs, I (15 July 2001). "A light stabilizer Tinuvin 770-induced toxic injury of adult rat cardiac myocytes". Forensic Science International. 119 (3): 322–7. doi:10.1016/s0379-0738(00)00462-x. PMID 11390147.

[8] Krepuska, M; Hubay, M; Zima, E; Kovacs, A; Kekesi, V; Kalasz, H; Szilagyi, B; Merkely, B; Sotonyi, P (2018). "Hemodynamic Effects of the Light Stabilizer Tinuvin 770 in Dogs In Vivo". The Open Medicinal Chemistry Journal. 12: 88–97. doi:10.2174/1874104501812010088. PMC 6142673. PMID 30288180.

[9] Sótonyi, P; Merkely, B; Hubay, M; Járay, J; Zima, E; Soós, P; Kovács, A; Szentmáriay, I (February 2004). "Comparative study on cardiotoxic effect of Tinuvin 770: a light stabilizer of medical plastics in rat model". Toxicological Sciences. 77 (2): 368–74. doi:10.1093/toxsci/kfh025. PMID 14657520.

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