tinyatoxin

Also known as Daphnetoxin

Tinyatoxin (TTX or TTN) is an analog of the neurotoxin resiniferatoxin. It occurs naturally in Euphorbia poissonii.

Key facts

Pepper.heat: Above peak
Pepper.scoville: 5,300,000,000

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Chemical data

Formula: C36H38O8
Molecular weight: 598.7 g/mol
IUPAC name: [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxyphenyl)acetate
SMILES: C[C@@H]1C[C@]2([C@H]3[C@H]4[C@]1([C@@H]5C=C(C(=O)[C@]5(CC(=C4)COC(=O)CC6=CC=C(C=C6)O)O)C)O[C@](O3)(O2)CC7=CC=CC=C7)C(=C)C
InChIKey: WWZMXEIBZCEIFB-ACAXUWNGSA-N
XLogP: 4.5
Polar surface area: 112 Å²
H-bond donors: 2
H-bond acceptors: 8
Formal charge: 0

via PubChem

Wikidata facts

Mass: 598.256668176

Show 5 more facts

isomeric SMILES: C[C@@H]1C[C@]2([C@H]3[C@H]4[C@]1([C@@H]5C=C(C(=O)[C@]5(CC(=C4)COC(=O)CC6=CC=C(C=C6)O)O)C)O[C@](O3)(O2)CC7=CC=CC=C7)C(=C)C
canonical SMILES: CC1CC2(C3C4C1(C5C=C(C(=O)C5(CC(=C4)COC(=O)CC6=CC=C(C=C6)O)O)C)OC(O3)(O2)CC7=CC=CC=C7)C(=C)C
found in taxon: Euphorbia lactea
chemical formula: C₃₆H₃₈O₈
Scoville grade: 5300000000

Sources (1)

wikidata.org

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Encyclopedic overview

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Contents

References

Tinyatoxin (TTX or TTN) is an analog of the neurotoxin resiniferatoxin. It occurs naturally in Euphorbia poissonii.

It is a neurotoxin that acts via full agonism of the vanilloid receptors of sensory nerves. Tinyatoxin has a potential for pharmaceutical uses similar to uses of capsaicin. Tinyatoxin is about one third as strong as resiniferatoxin but is still an ultrapotent analogue of capsaicin, with a heat intensity estimate of 300 to 350 times that of capsaicin.

Excerpted from Wikipedia’s “tinyatoxin” article, available under the CC BY-SA 4.0 licence.

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