Tinyatoxin

Tinyatoxin
Heat	Above peak
Scoville scale	5,300,000,000 SHU

Tinyatoxin
Identifiers
CAS Number	58821-95-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9603;
ChemSpider	32701427;
ECHA InfoCard	100.165.094
MeSH	tinyatoxin
PubChem CID	442098;
UNII	WN080Z1OL0 ;
CompTox Dashboard (EPA)	DTXSID40974337 ;
	InChI InChI=1S/C36H38O8/c1-21(2)34-17-23(4)36-28(32(34)42-35(43-34,44-36)19-25-8-6-5-7-9-25)15-26(18-33(40)29(36)14-22(3)31(33)39)20-41-30(38)16-24-10-12-27(37)13-11-24/h5-15,23,28-29,32,37,40H,1,16-20H2,2-4H3/t23-,28+,29-,32-,33-,34-,35-,36-/m1/s1 Key: WWZMXEIBZCEIFB-ACAXUWNGSA-N;
	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)Cc6ccc(cc6)O)O)C)O[C@](O3)(O2)Cc7ccccc7)C(=C)C;
Properties
Chemical formula	C36H38O8
Molar mass	598.692 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tinyatoxin (TTX or TTN) is an analog of the neurotoxin resiniferatoxin. It occurs naturally in Euphorbia poissonii.^[1]

It is a neurotoxin that acts via full agonism of the vanilloid receptors of sensory nerves.^[2] 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.

References

^ Euphorbia poissonii in BoDD – Botanical Dermatology Database
^ Szallasi, A. & Blumberg, P.M. (1991). "Characterization of vanilloid receptors in the dorsal horn of pig spinal cord". Brain Res. 547 (2): 335–338. doi:10.1016/0006-8993(91)90982-2. PMID 1884211. S2CID 25052101.

[BoDD-1] Euphorbia poissonii in BoDD – Botanical Dermatology Database

[2] Szallasi, A. & Blumberg, P.M. (1991). "Characterization of vanilloid receptors in the dorsal horn of pig spinal cord". Brain Res. 547 (2): 335–338. doi:10.1016/0006-8993(91)90982-2. PMID 1884211. S2CID 25052101.

[1]

[2]

Identifiers

CAS Number	58821-95-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9603
ChemSpider	32701427
ECHA InfoCard	100.165.094
MeSH	tinyatoxin
PubChem CID	442098
UNII	WN080Z1OL0
CompTox Dashboard (EPA)	DTXSID40974337
InChI InChI=1S/C36H38O8/c1-21(2)34-17-23(4)36-28(32(34)42-35(43-34,44-36)19-25-8-6-5-7-9-25)15-26(18-33(40)29(36)14-22(3)31(33)39)20-41-30(38)16-24-10-12-27(37)13-11-24/h5-15,23,28-29,32,37,40H,1,16-20H2,2-4H3/t23-,28+,29-,32-,33-,34-,35-,36-/m1/s1 Key: WWZMXEIBZCEIFB-ACAXUWNGSA-N
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)Cc6ccc(cc6)O)O)C)O[C@](O3)(O2)Cc7ccccc7)C(=C)C
Properties
Chemical formula	C₃₆H₃₈O₈
Molar mass	598.692 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).