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The chemistry of Salvia divinorum - PDF Document (6 M) |
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| Access Rights |
Open Access |
| Citation |
Munro, T. A. (2006). The chemistry of Salvia divinorum. PhD thesis, Science: School of Chemistry, University of Melbourne. |
| Handle |
10187/742 |
| Title |
The chemistry of Salvia divinorum |
| Creator |
Munro, Thomas Anthony |
| Date |
2006-04 |
| Subject / Keywords |
Salvia divinorum, salvinorin, divinatorin, terpenoid, neoclerodane diterpenoid, alkaloid, Valdes, Diaz, epimerization, kappa opioid receptor, HIV, activated carbon, amorphous solid, legal status, systematic name |
| Abstract |
Salvia divinorum is a hallucinogenic sage used to treat illness by the Mazatec Indians of Mexico. Salvinorin A (1a), a neoclerodane diterpenoid isolated from the plant, is a potent, selective agonist at the kappa opioid receptor (KOR), and is the first non-nitrogenous opioid. The plant is used recreationally as a hallucinogen, but is unpopular due to its dysphoric effects. 1a has been prohibited in Australia under an invalid systematic name. An early report of psychoactive alkaloids in S. divinorum proved to be irreproducible. Similarly, tests in mice suggesting the presence of psychoactive compounds other than 1a were confounded and therefore unreliable. In this work, an improved isolation method for 1a was developed, using filtration through activated carbon to decolourise the crude extract. Six new diterpenoids were isolated: salvinorins D–F (1d–1f) and divinatorins A–C (28a–28c). Five known terpenoids not previously reported from this species were also isolated. The structure–activity relationships of 1a were evaluated via selective modifications of each functional group. Useful synthetic methods are reviewed, including the first thorough review of furanolactone hydrogenations. Testing of the derivatives at the KOR suggests that the methyl ester and furan ring of 1a are required for activity, but that the lactone and ketone functionalities are not. Other compounds from S. divinorum did not bind to the KOR, suggesting that 1a is the plant’s active principle. |
| Type |
PhD thesis |
| Language |
eng |
| Notes |
© 2006 Thomas Anthony Munro. |
| Publication Status |
Unpublished |
| Peer Reviewed |
Peer Reviewed |
| Faculty/Department |
Science: School of Chemistry |
| Faculty/Department |
Chemistry |
| Institution |
University of Melbourne |
| Collection |
Research Collections (UMER) |
| Rights |
Terms and Conditions: Copyright in works deposited in the University of Melbourne Eprints Repository (UMER) is retained by the copyright owner. The work may not be altered without permission from the copyright owner. Readers may only, download, print, and save electronic copies of whole works for their own personal non-commercial use. Any use that exceeds these limits requires permission from the copyright owner. Attribution is essential when quoting or paraphrasing from these works. |
| PID |
66891 |
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