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

BTMPS
Names
Other names
Bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate
Identifiers
3D model (JSmol)
ChemSpider
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
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).

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

Production and reactions

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Its production involves sebacic acid and tetramethylpiperidinol.[4]

Potential medical significance

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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

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  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.