Batrachotoxin

Batrachotoxin
	; Skeletal formula of batrachotoxin
	; Stick model of batrachotoxin based on the crystal structure of batrachotoxinin A O-p-bromobenzoate
	; Ball-and-stick model of batrachotoxin, as above
Names
	Other names 3α,9α-epoxy-14β,18-(2′-oxyethyl-N-methylamino)-5β-pregna-7,16-diene-3β,11α,20α-triol 20α-2,4-dimethylpyrrole-3-carboxylate
Identifiers
CAS Number	23509-16-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	10310314 ;
IUPHAR/BPS	2619;
PubChem CID	6324647;
UNII	TSG6XHX09R ;
CompTox Dashboard (EPA)	DTXSID50893767 ;
	InChI InChI=1S/C31H42N2O6/c1-18-16-32-19(2)25(18)26(35)38-20(3)22-8-9-30-23-7-6-21-14-29(36)11-10-27(21,4)31(23,39-29)24(34)15-28(22,30)17-33(5)12-13-37-30/h7-8,16,20-21,24,32,34,36H,6,9-15,17H2,1-5H3/t20-,21+,24+,27-,28-,29+,30-,31-/m0/s1 Key: ISNYUQWBWALXEY-OMIQOYQYSA-N ; InChI=1/C31H42N2O6/c1-18-16-32-19(2)25(18)26(35)38-20(3)22-8-9-30-23-7-6-21-14-29(36)11-10-27(21,4)31(23,39-29)24(34)15-28(22,30)17-33(5)12-13-37-30/h7-8,16,20-21,24,32,34,36H,6,9-15,17H2,1-5H3/t20-,21+,24+,27-,28-,29+,30-,31-/m0/s1 Key: ISNYUQWBWALXEY-OMIQOYQYBY;
	SMILES Cc1c[nH]c(C)c1C(=O)O[C@@H](C)C1=CC[C@@]23OCCN(C)C[C@@]12C[C@@H](O)[C@]12O[C@]4(O)CC[C@@]1(C)[C@H](CC=C23)C4;
Properties
Chemical formula	C31H42N2O6
Molar mass	538.685 g·mol−1
Density	1.304 g/mL
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Highly toxic
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	2 μg/kg; (mouse, sub-cutaneous)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Batrachotoxin (BTX) is an extremely potent cardiotoxic and neurotoxic steroidal alkaloid found in certain species of beetles, birds, and frogs. The name is from the Greek word βάτραχος, bátrachos, 'frog'.^[3] Structurally-related chemical compounds are often referred to collectively as batrachotoxins. In certain frogs, this alkaloid is present mostly on the skin. Such frogs are among those used for poisoning darts. Batrachotoxin binds to and irreversibly opens the sodium channels of nerve cells and prevents them from closing, resulting in paralysis and death. No antidote is known.

^ ^a ^b Karle, I. L.; Karle, J. (1969). "The structural formula and crystal structure of the O-p-bromobenzoate derivative of batrachotoxinin A, C₃₁H₃₈NO₆Br, a frog venom and steroidal alkaloid". Acta Crystallogr. B. 25 (3): 428–434. Bibcode:1969AcCrB..25..428K. doi:10.1107/S056774086900238X. PMID 5820223. S2CID 28609553.
^ Daly, J. W.; Journal of the American Chemical Society 1965, V87(1), P124-6 CAPLUS
^ The Merck Index. Entry 1009. p. 167.

[Karle&Karle1969-1] Karle, I. L.; Karle, J. (1969). "The structural formula and crystal structure of the O-p-bromobenzoate derivative of batrachotoxinin A, C₃₁H₃₈NO₆Br, a frog venom and steroidal alkaloid". Acta Crystallogr. B. 25 (3): 428–434. Bibcode:1969AcCrB..25..428K. doi:10.1107/S056774086900238X. PMID 5820223. S2CID 28609553.

[2] Daly, J. W.; Journal of the American Chemical Society 1965, V87(1), P124-6 CAPLUS

[3] The Merck Index. Entry 1009. p. 167.

[1]

[2]

[3]

Names
Skeletal formula of batrachotoxin
Stick model of batrachotoxin based on the crystal structure of batrachotoxinin A O-p-bromobenzoate^[1]
Ball-and-stick model of batrachotoxin, as above^[1]
Other names 3α,9α-epoxy-14β,18-(2′-oxyethyl-N-methylamino)-5β-pregna-7,16-diene-3β,11α,20α-triol 20α-2,4-dimethylpyrrole-3-carboxylate
Identifiers
CAS Number	23509-16-2^Y
3D model (JSmol)	Interactive image
ChemSpider	10310314^Y
IUPHAR/BPS	2619
PubChem CID	6324647
UNII	TSG6XHX09R^Y
CompTox Dashboard (EPA)	DTXSID50893767
InChI InChI=1S/C31H42N2O6/c1-18-16-32-19(2)25(18)26(35)38-20(3)22-8-9-30-23-7-6-21-14-29(36)11-10-27(21,4)31(23,39-29)24(34)15-28(22,30)17-33(5)12-13-37-30/h7-8,16,20-21,24,32,34,36H,6,9-15,17H2,1-5H3/t20-,21+,24+,27-,28-,29+,30-,31-/m0/s1^Y Key: ISNYUQWBWALXEY-OMIQOYQYSA-N^Y InChI=1/C31H42N2O6/c1-18-16-32-19(2)25(18)26(35)38-20(3)22-8-9-30-23-7-6-21-14-29(36)11-10-27(21,4)31(23,39-29)24(34)15-28(22,30)17-33(5)12-13-37-30/h7-8,16,20-21,24,32,34,36H,6,9-15,17H2,1-5H3/t20-,21+,24+,27-,28-,29+,30-,31-/m0/s1 Key: ISNYUQWBWALXEY-OMIQOYQYBY
SMILES Cc1c[nH]c(C)c1C(=O)O[C@@H](C)C1=CC[C@@]23OCCN(C)C[C@@]12C[C@@H](O)[C@]12O[C@]4(O)CC[C@@]1(C)[C@H](CC=C23)C4
Properties
Chemical formula	C₃₁H₄₂N₂O₆
Molar mass	538.685 g·mol⁻¹
Density	1.304 g/mL ^[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Highly toxic
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	2 μg/kg (mouse, sub-cutaneous)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references