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Bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate

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BTMPS
Names
Other names
Trade names
  • Tinuvin 770 (BASF)
  • Lowilite 77 (SI Group)
  • ADK STAB LA-77 (Adeka)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.052.899 Edit this at Wikidata
EC Number
  • 258-207-9
MeSH C083752
UNII
  • 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
  • CC1(C)CC(CC(C)(C)N1)OC(=O)CCCCCCCCC(=O)OC2CC(C)(C)NC(C)(C)C2
Properties
C28H52N2O4
Molar mass 480.734 g·mol−1
Appearance white powder (aminoxyl form is orange-red)
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).

Bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate (abbreviated BTMPS) is a hindered amine light stabilizer used to protect plastics and coatings such as paint from oxidation caused by weathering. like most compounds of this class, it's active form is an aminoxyl radical.

In 2024 it was detected as an adulterant in illicitly sold fentanyl in the United States.[1][2]

Production and reactions

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It is produced by the esterification of sebacic acid and tetramethylpiperidinol (or its oxidised form 4-Hydroxy-TEMPO).[3]

Potential medical significance

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It is capable of inhibiting nicotinic acetylcholine receptors.[4] Additionally, it is a potent blocker of L-type calcium channels.[5][6] It is also able to induce dose-dependent hemodynamic alterations.[7] Similar to early calcium channel blockers, it can precipitate adrenergic release.[8]

References

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  1. ^ "BTMPS". The Center for Forensic Science Research & Education.
  2. ^ 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.
  3. ^ "Preparation method of hindered amine light stabilizer 770". 13 August 2014. Archived from the original on 20 September 2024. Retrieved 20 September 2024.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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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