Epibatidine

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Structural formula
Structure of (+) - epibatidine
General
Surname Epibatidine
other names
  • (+) - epibatidine
  • (1 R , 2 R , 4 S ) - (+) - 2- (6-chloro-3-pyridinyl) -7-azabicyclo [2.2.1] heptane
Molecular formula C 11 H 13 ClN 2
Brief description

white solid [(+) - epibatidine dihydrochloride]

External identifiers / databases
CAS number
  • 140111-52-0 [(+) - epibatidine]
  • 166374-43-2 [(+) - epibatidine · di hydrochloride ]
EC number 634-286-9
ECHA InfoCard 100.162.281
PubChem 3073763
DrugBank DB07720
Wikidata Q423783
properties
Molar mass 208.69 g mol −1 [(+) - epibatidine]
Physical state

liquid [(+) - epibatidine]

Melting point

216–217 ° C [(+) - epibatidine dihydrochloride]

solubility

poor in water (10 g · l −1 [(+) - epibatidine · dihydrochloride] )

safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 300-310
P: 264-280-302 + 350-310
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 ) .

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

  1. a b c d e data sheet (+) - Epibatidine dihydrochloride from Sigma-Aldrich , accessed on August 16, 2019 ( PDF ).
  2. ^ 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 .
  3. ^ Matthew J. Dowd: Epibatidine. In: phc.vcu.edu. Archived from the original on August 8, 2009 ; accessed on February 16, 2017 .
  4. 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.