Grayanotoxane-3,5,6,10,14,16-hexol

HCID 207666
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Basic information

CAS
30460-38-9
Standard SMILES
CC1(C)[C@H](O)C[C@H]2[C@](C)(O)[C@@H]3CCC4[C@H](O)C3(C[C@@H](O)[C@@]21O)C[C@@]4(C)O
InChIKey
BWMFRQKICHXLSH-PMDFNMFYSA-N
Molecular formula
C20H34O6
Average molar mass
370.5 g/mol
Monoisotopic mass
370.23553881

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
Grayanotoxane-3,5,6,10,14,16-hexol
IUPAC
(3R,4R,6R,8S,9R,10R,14R,16S)-5,5,9,14-tetramethyltetracyclo[11.2.1.01,10.04,8]hexadecane-3,4,6,9,14,16-hexol

Names & synonyms

DTXSID80952790Grayanotoxane-3,5,6,10,14,16-hexol30460-38-9RefChem:1086182DTXCID5013808643-Epigrayanotoxin III3-epi-Grayanotoxin III(3-alpha,6-beta,14R)Grayanotoxane-3,5,6,10,14,16-hexolGrayanotoxane-3,5,6,10,14,16-hexol, (3-alpha,6-beta,14R)-(14S)-Grayanotoxane-3alpha,5,6beta,10,14,16-hexol

Database identifiers

CAS
30460-38-9
PubChem CID
207666
DTXSID
DTXSID80952790

Properties

Computed structural propertiesFilling in

XLogP
0.3
Topological polar surface area
121 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
6
Rotatable bonds
0
Heavy atoms
26

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 · 1 item

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)

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