Epibatidine
Structural formula | |||||||||||||||||||
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General | |||||||||||||||||||
Surname | Epibatidine | ||||||||||||||||||
other names |
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Molecular formula | C 11 H 13 ClN 2 | ||||||||||||||||||
Brief description |
white solid [(+) - epibatidine dihydrochloride] |
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properties | |||||||||||||||||||
Molar mass | 208.69 g mol −1 [(+) - epibatidine] | ||||||||||||||||||
Physical state |
liquid [(+) - epibatidine] |
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Melting point |
216–217 ° C [(+) - epibatidine dihydrochloride] |
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solubility |
poor in water (10 g · l −1 [(+) - epibatidine · dihydrochloride] ) |
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safety instructions | |||||||||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Epibatidin is an alkaloid with a bicyclic structure obtained from the skin gland secretion of the poison dart frog ( Epipedobates tricolor ) .
It occurs in amounts less than 1 mg per frog. Epibatidine exceeds the analgesic effect of morphine by about 200 times and the affinity of nicotine for nicotinic acetylcholine receptors by 120 times. Epibatidine is a potent analgesic , but too toxic for human use. Its effect is similar to other acetylcholine receptor blockers such as nicotine from tobacco , anatoxin A from some cyanobacteria , coniin from the spotted hemlock , cytisine from golden rain , and arecoline from betel nuts .
Based on epibatidine, the only slightly toxic non-opioid analgesic Tebanicline ( ABT-594 ) was developed in 1996 , which is one of the azetidines . Due to gastrointestinal side effects, the trials in phase II were stopped, but research on similar substances is being continued.
See also
Individual evidence
- ↑ a b c d e data sheet (+) - Epibatidine dihydrochloride from Sigma-Aldrich , accessed on August 16, 2019 ( PDF ).
- ^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 616, ISBN 978-0-911910-00-1 .
- ^ Matthew J. Dowd: Epibatidine. In: phc.vcu.edu. Archived from the original on August 8, 2009 ; accessed on February 16, 2017 .
- ↑ Zin Sig Kim: Asymmetrical synthesis of 1,3-amino alcohols and their application for the synthesis of azetidines and 1-azabicyclics (PDF; 1.1 MB), TH Aachen , dissertation, 2006.