Tetrodotoxin

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Names

[ Name ]:
Tetrodotoxin

[Synonym ]:
5,9:7,10a-Dimethano-10aH-[1,3]dioxocino[6,5-d]pyrimidine-4,7,10,11,12-pentol, octahydro-12-(hydroxymethyl)-2-imino-, (4R,4aR,5R,7S,9S,10S,10aR,11S,12S)-
Tetrodotoxin
EINECS 224-458-8
Tetradotoxin
Fugu Toxin
spheroidine
(–)-Tetrodotoxin
(1R,5R,6R,7R,9S,11S,12S,13S,14S)-3-Amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1.0]tetradec-2-ene-5,9,12,13,14-pentol
(4R,4aR,5R,7S,9S,10S,10aR,11S,12S)-octahydro-12-(hydroxymethyl)-2-imino-5,9:7,10a-dimethano-10aH-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol
maculotoxin
tarichatoxin
tetrodontoxin
tetrdotoxin
Fugu poison,Maculotoxin,TTX
MFCD00213719
fugu poison

Chemical & Physical Properties

[ Density]:
2.8±0.1 g/cm3

[ Boiling Point ]:
702.6±70.0 °C at 760 mmHg

[ Melting Point ]:
225ºC dec

[ Molecular Formula ]:
C₁₁H₁₇N₃O₈

[ Molecular Weight ]:
319.268

[ Flash Point ]:
378.7±35.7 °C

[ Exact Mass ]:
319.101563

[ PSA ]:
187.75000

[ LogP ]:
2.16

[ Vapour Pressure ]:
0.0±5.0 mmHg at 25°C

[ Index of Refraction ]:
2.087

[ Water Solubility ]:
H2O: stable at pH 4-5 if stored frozensoluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: IO1450000

CAS REGISTRY NUMBER :: 4368-28-9

BEILSTEIN REFERENCE NO. :: 0049176

LAST UPDATED :: 199710

DATA ITEMS CITED :: 19

MOLECULAR FORMULA :: C11-H17-N3-O8

MOLECULAR WEIGHT :: 319.31

WISWESSER LINE NOTATION :: T66 B6 D6/B-H/DM A B- C 2BD M AO B-O DX EMYMTJ CQ EQ GQ G1Q JQ LUM

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 15 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 144,1100,1964

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 334 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: SKEZAP Shokuhin Eiseigaku Zasshi. Food Hygiene Journal. (Nippon Shokuhin Eisei Gakkai c/o Shokuhin Eisei Senta, 2-6-1 Jingumae, Shibuya-ku, Tokyo 150, Japan) V.1- 1960- Volume(issue)/page/year: 14,186,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 144,1100,1964

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 4,331,1971

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7300 ng/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: SKEZAP Shokuhin Eiseigaku Zasshi. Food Hygiene Journal. (Nippon Shokuhin Eisei Gakkai c/o Shokuhin Eisei Senta, 2-6-1 Jingumae, Shibuya-ku, Tokyo 150, Japan) V.1- 1960- Volume(issue)/page/year: 14,186,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 600 ng/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia

REFERENCE :: SKEZAP Shokuhin Eiseigaku Zasshi. Food Hygiene Journal. (Nippon Shokuhin Eisei Gakkai c/o Shokuhin Eisei Senta, 2-6-1 Jingumae, Shibuya-ku, Tokyo 150, Japan) V.1- 1960- Volume(issue)/page/year: 14,186,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8700 pg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IGAYAY Igaku No Ayumi. Progress in Medicine. (Ishiyaku Shuppan K.K., 1-7-10, Honkomagom, Bunkyo-ku, Tokyo, Japan) V.1- 1946- Volume(issue)/page/year: 112,861,1980

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 7500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HXPHAU Handbuch der Experimentellen Pharmakologie. (Berlin, Ger.) New series: V.1-49, 1935-78. For publisher information, see HEPHD2. Volume(issue)/page/year: 6,63,1938

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 650 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HXPHAU Handbuch der Experimentellen Pharmakologie. (Berlin, Ger.) New series: V.1-49, 1935-78. For publisher information, see HEPHD2. Volume(issue)/page/year: 6,63,1938

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HXPHAU Handbuch der Experimentellen Pharmakologie. (Berlin, Ger.) New series: V.1-49, 1935-78. For publisher information, see HEPHD2. Volume(issue)/page/year: 6,63,1938

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HXPHAU Handbuch der Experimentellen Pharmakologie. (Berlin, Ger.) New series: V.1-49, 1935-78. For publisher information, see HEPHD2. Volume(issue)/page/year: 6,63,1938

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 25 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HXPHAU Handbuch der Experimentellen Pharmakologie. (Berlin, Ger.) New series: V.1-49, 1935-78. For publisher information, see HEPHD2. Volume(issue)/page/year: 6,63,1938

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 4 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HXPHAU Handbuch der Experimentellen Pharmakologie. (Berlin, Ger.) New series: V.1-49, 1935-78. For publisher information, see HEPHD2. Volume(issue)/page/year: 6,63,1938

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraspinal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 80 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HXPHAU Handbuch der Experimentellen Pharmakologie. (Berlin, Ger.) New series: V.1-49, 1935-78. For publisher information, see HEPHD2. Volume(issue)/page/year: 6,63,1938

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 14 ug/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change

REFERENCE :: TOXIA6 Toxicon. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.1- 1962- Volume(issue)/page/year: 5,25,1967

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 15 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 144,1100,1964 *** REVIEWS *** TOXICOLOGY REVIEW TRBMAV Texas Reports on Biology and Medicine. (Galveston, TX) V.1-41(2), 1943-81/82. Discontinued. Volume(issue)/page/year: 33,183,1975

Safety Information

[ Hazard Codes ]:
T+: Very toxic;

[ Risk Phrases ]:
R26/27/28

[ Safety Phrases ]:
S22-S36/37/39-S45

[ RIDADR ]:
UN 3462 6.1/PG 1

[ WGK Germany ]:
3

[ RTECS ]:
IO1450000

[ Packaging Group ]:
I

[ Hazard Class ]:
6.1(a)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

(E)-2-((2R,5S,6R)-2-((benzyloxy)methoxy)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-hydroxycyclohex-3-en-1-ylidene)acetaldehyde
(1S,4R,6R,E)-4-((benzyloxy)methoxy)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(2-hydroxyethylidene)cyclohex-2-en-1-ol
methyl (E)-2-((2R,5S,6R)-2-((benzyloxy)methoxy)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-hydroxycyclohex-3-en-1-ylidene)acetate
((1S,2R,3S,4R,5S,6R)-2-acetoxy-5-((benzyloxy)methoxy)-4-((tert-butoxycarbonyl)amino)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(2-oxoethyl)-7-oxabicyclo[4.1.0]heptan-1-yl)methyl benzoate
(1S,3S,5R,8S,8aR)-1-(((tert-butyldimethylsilyl)oxy)methyl)-7-(((tert-butyldiphenylsilyl)oxy)methyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl benzoate
(1S,5R,8S,8aR)-5-((benzyloxy)methoxy)-7-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxy-1-(hydroxymethyl)-3,5,8,8a-tetrahydro-1H-isochromen-8-yl benzoate
((1S,2R,3S,4R,5S,6R)-2-acetoxy-5-((benzyloxy)methoxy)-4-((tert-butoxycarbonyl)amino)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(2-hydroxyethyl)-7-oxabicyclo[4.1.0]heptan-1-yl)methyl benzoate
methyl 2-((1S,5R,6R,9R)-6-((benzyloxy)methoxy)-8-(((tert-butyldiphenylsilyl)oxy)methyl)-9-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-oxo-2-oxa-4-azabicyclo[3.3.1]non-7-en-5-yl)acetate
(1S,5R,8S,8aR)-1-(acetoxymethyl)-5-((benzyloxy)methoxy)-7-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl benzoate