Basic information
- CAS
4678-44-8- Standard SMILES
C=C1[C@@H]2CC[C@@H]3C(O)[C@@]2(C[C@@H](O)[C@@]2(O)[C@H]1C[C@H](O)C2(C)C)C[C@@]3(C)O- InChIKey
KEOQZUCOGXIEQR-BBLSUVPKSA-N- Molecular formula
- C20H32O5
- Average molar mass
- 352.5 g/mol
- Monoisotopic mass
- 352.22497412
Overview
Grayanotoxins are toxins found in rhododendrons and other plants of the family Ericaceae. It can be found in honey made from their nectar and cause a very rare poisonous reaction called grayanotoxin poisoning, honey intoxication, or rhododendron poisoning. (L1251)
Names & identifiers
- Preferred name
- Grayanotox-10-ene-3beta,5,6beta,14,16-pentol
- IUPAC
- (1S,3R,4R,6S,8S,10S,13R,14R)-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.01,10.04,8]hexadecane-3,4,6,14,16-pentol
Names & synonyms
orb1986001HY-N7570AKOS040751952CS-0133964T31993Grayanotox-10-ene-3beta,5,6beta,14,16-pentol
Database identifiers
- CAS
4678-44-8- PubChem CID
- 107976
- DTXSID
DTXSID20897035
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 617
Safety & regulation
Toxicology
TreatmentMedical treatment is not often needed but sometimes atropine therapy, vasopressors and other agents are used to mitigate symptoms. (L1251)
Health EffectsGrayanotoxins affect the nervous system but are not usually fatal. (L1251)
Exposure RoutesOral (ingestion) (L1817) ; dermal (L1817)
Toxicity SummaryGrayanotoxins bind to specific sodium ion channels in cell membranes. The grayanotoxins prevent inactivation, leaving excitable cells depolarized. (L1251)
Signs and Symptoms
Initial symptoms include excessive salivation, perspiration, vomiting, dizziness, weakness and paresthesia in the extremities and around the mouth, low blood pressure and sinus bradycardia. In higher doses symptoms can include loss of coordination, severe and progressive muscular weakness, bradycardia (and, paradoxically, ventricular tachycardia), and nodal rhythm or Wolff-Parkinson-White syndrome. (L1251)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Uses & manufacturing
UsesGrayanotoxins are toxins found in rhododendrons and other plants of the family Ericaceae. (L1251)
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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