Synthesis of the 3-(3,4,5-Trimethoxyphenyl)-pyrrolidine: A New Conformationally Constrained Mescaline Analogue
Ricardo de L. Barreto, Laura B. L. R. Nascimbem, Carlos Roque D. Correia
Synthetic Communications June 1, 2007 DOI: 10.1080/00397910701356504 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | Mescaline |
| Keywords | Pyrrolidine Hemiaminal Stereochemistry Trifluoroacetic anhydride Thebaine Organic chemistry |
| Citations | 8 |
| Key points | A new mescaline analogue was synthesized via a concise four-step route featuring a Heck arylation, with potential activity towards 5-HT2 dopamine receptors. |
Abstract
Abstract The total synthesis of the 3‐(3,4,5-trimethoxyphenyl)-pyrrolidine, a new and conformationally constrained mescaline analogue, was accomplished in a concise and efficient manner. The synthetic route encompassed only 4 steps from the starting N-Cbz-3-pyrrolidine, in 46% overall yield. The route features a highly effective Heck arylation of the non-activated olefin N-Cbz-3-pyrrolidine with the 3,4,5-trimethoxybenzene diazonium tetrafluoroborate. The hemiaminal (lactamol) Heck adduct was converted to the mescaline analogue in a sequence of reactions: (a) dehydration of the intermediate hemiaminal 3 with trifluoroacetic acid anhydride, (b) hydrogenation/hydrogenolysis of the endocyclic enecarbamate 6 with H2-Pd/C, and (c) formation of the rather stable mescaline analogue in the form of a hydrochloride salt. The target molecule constitutes a new mescaline analogue with potential activity towards 5‐HT2 dopamine receptors.
Comparable studies
Other theoretical and historical papers on mescaline, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Schizophrenia: A New Approach. II. Result of a Year's Research | 1954 | Theoretical or philosophical paper | |
| Thought insertion as a self-disturbance: An integration of predictive coding and phenomenological approaches | 2016 | Theoretical or philosophical paper | |
| Entactogens: How the Name for a Novel Class of Psychoactive Agents Originated | 2022 | Theoretical or philosophical paper | |
| Steric and Electronic Relationships among Some Hallucinogenic Compounds | 1970 | Theoretical or philosophical paper | |
| EFFECT OF DRUGS One individual | 1952 | Theoretical or philosophical paper | n = 1 |
Citations in the library
Cites 6
- Synthesis of a Tricyclic Mescaline Analogue by Catalytic C−H Bond Activation Organic Letters March 22, 2003
- Dihydrobenzofuran Analogues of Hallucinogens. 4. Mescaline Derivatives Journal of Medicinal Chemistry September 1, 1997
- Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogs Journal of Medicinal Chemistry February 1, 1977
- Effects of mescaline and some of its analogs on cholinergic neuromuscular transmission Neuropharmacology February 1, 1993
- Sulfur analogues of psychotomimetic agents. Monothio analogs of mescaline and isomescaline Journal of Medicinal Chemistry November 1, 1981
and 1 more in the library