The Discovery of Capsazepine, the First Competitive Antagonist of the Sensory Neuron Excitants Capsaicin and Resiniferatoxin was written by Walpole, Christopher S. J.;Bevan, Stuart;Bovermann, Guenter;Boelsterli, Johann J.;Breckenridge, Robin;Davies, John W.;Hughes, Glyn A.;James, Iain;Oberer, Lukas. And the article was included in Journal of Medicinal Chemistry in 1994.Name: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride This article mentions the following:
Capsaicin and resiniferatoxin are natural products which act specifically on a subset of primary afferent sensory neurons to open a novel cation-selective ion channel in the plasma membrane. Conformationally constrained analogs I [R1 = OH, OMe, H; R2 = OH, OMe; R3 = H, OH; R4 = octyl, 4-ClC6H4CH2CH2; n = 1-3] of these mols. were prepared The resulting compounds provided agonists of comparable potency to unconstrained analogs as well as a moderately potent antagonist, capsazepine (I, R1 = R2 = OH, R3 = H, R4 = 4-ClC6H4CH2CH2, n = 3). This compound is the first competitive antagonist of capsaicin and resiniferatoxin to be described and is active in various systems, in vitro and in vivo. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Name: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride).
6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. An oxidative C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents is mediated by diethyl azodicarboxylate (DEAD). This C-H activation under metal-free conditions delivers target compounds, including some naturally occurring alkaloids, in good yields.Name: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride
Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem