1,2,2,6,6-Pentamethylpiperidine - CAS 79-55-0
Not Intended for Therapeutic Use. For research use only.
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1,2,2,6,6-Pentamethylpiperidine is a ganglion-blocking drug. It is one of the most strongly basic tertiary amine. It is ued as an oral treatment for hypertension and used as an organic structure directing agent (OSDA) in the synthesis of the RTH-type zeolites. It is also used in the synthesis of BN-fused polycyclic aromatic molecules for potential application to electronic materials and apparatus. It is also a catalyst for the chemoselective silylation of benzylic alcohols.
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CAS 79-55-0 1,2,2,6,6-Pentamethylpiperidine

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Reference Reading

1.Design, synthesis and photostability of novel 1,8-naphthalimide PAMAM light-harvesting dendrons.
Georgiev NI1, Bojinov VB. J Fluoresc. 2011 Jan;21(1):51-63. doi: 10.1007/s10895-010-0689-y. Epub 2010 Jul 17.
This paper reports on the divergent synthesis, photophysical properties and photodegradation of novel PAMAM dendrons, core and peripherally functionalized with 1,8-naphthalimide fluorophores. The novel compounds were configured as light-harvesting antennae where the system surface is labeled with blue emitting 4-allyloxy-1,8-naphthalimide "donor" fluorophores capable of absorbing light and efficiently transferring the energy to a single yellow-green emitting 4-alkylamino-1,8-naphthalimide "acceptor" dye. The focal 1,8-naphthalimide fluorophores in the antennae were modified with a HALS fragment (2,2,6,6-tetramethylpiperidine or 1,2,2,6,6-pentamethylpiperidine) with a view to improve their photostability. Novel light-harvesting systems showed highly efficient energy transfer, depending on the volume of the core substituent. Due to the HALS fragments the chromophoric system of the novel antennae showed higher photostability, while the photostability of the PAMAM scaffold was found to be lower.
2.Optimization of palladium-catalyzed polyene cyclizations: suppression of competing hydride transfer from tertiary amines with Dabco and an unexpected hydride transfer from 1,4-dioxane.
Lau SY1, Andersen NG, Keay BA. Org Lett. 2001 Jan 25;3(2):181-4.
[figure: see text] This paper demonstrates that both 1,2,2,6,6-pentamethylpiperidine (PMP) and 1,4-dioxane can act as hydride donors in palladium-catalyzed polyene cyclizations of 2 and 3. Studies using PMP-d3 and dioxane-d8 either incorporate a deuterium atom into the monosubstituted product or completely inhibit the hydride transfer so that the second ring closure occurs in high yield. Dabco is the best substitute for PMP.
3.Pharmacological properties of pempidine (1:2:2:6:6-pentamethylpiperidine), a new ganglion-blocking compound.
CORNE SJ, EDGE ND. Br J Pharmacol Chemother. 1958 Sep;13(3):339-49.
Pempidine (1:2:2:6:6-pentamethylpiperidine) is a long-acting ganglion-blocking compound which is effective by mouth. By intravenous injection it has a similar potency to hexamethonium on the preganglionically stimulated nictitating membrane of the cat. The compound blocks the effects of intravenous nicotine and of peripheral vagal stimulation on the blood pressure; it also causes dilatation of the pupil after removal of the sympathetic innervation. On the guinea-pig ileum, the predominant effect of the compound is to inhibit nicotine contractions. Pempidine is well absorbed from the gastro-intestinal tract as judged by (a) the low ratio (6.9) of oral to intravenous toxicities, (b) the rapid development of mydriasis in mice after oral administration of small doses, and (c) the rapid onset of hypotension when the compound is injected directly into the duodenum of anaesthetized cats. Other actions include neuromuscular paralysis of curare-like type when large doses of the compound are injected intravenously and central effects such as tremors which occur with near toxic doses.