TETRODOTOXIN

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TETRODOTOXIN

  • Name TETRODOTOXIN
  • CAS 4368-28-9
  • Purity 99%
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Product Details

Top quality factory supply 4368-28-9 TETRODOTOXIN at low price

  • Molecular Formula: C11H17N3O8
  • Molecular Weight: 319.271
  • Appearance/Colour: white powder 
  • Vapor Pressure: 1.58E-27mmHg at 25°C 
  • Melting Point: 225oC dec 
  • Refractive Index: 2.087 
  • Boiling Point: 702.6 °C at 760 mmHg 
  • PKA: 8.76 (water); 9.4 (50% alc) 
  • Flash Point: 378.7 °C 
  • PSA： 192.32000 
  • Density: 2.78 g/cm3 
  • LogP: -6.03400 

TETRODOTOXIN(Cas 4368-28-9) Usage

Biological Activity

Selective inhibitor of Na + channel conductance. Binding is reversible and of high affinity (K d = 1-10 nM). Blocks in a use-dependent manner.

Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. When heated to decomposition it emits toxic fumes of Nox.

Toxicity evaluation

TTX is a selective sodium channel blocker that can block nerve and muscle conductions; action potentials are blocked while resting membrane potentials and resting membrane resistance are not affected. TTX blocks axonal transmission by lowering the conductance of sodium at nodes of Ranvier. Vomiting occurs because the toxin can act directly at or near the chemoreceptor trigger zone. Respiratory depression is caused by either a specific action of tetrodotoxin on the brain’s respiratory center or because paralysis of respiratory nerves and muscles occurs.

Definition

ChEBI: A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.

InChI:InChI=1/C11H17N3O8/c12-8-13-6(17)2-4-9(19,1-15)5-3(16)10(2,14-8)7(18)11(20,21-4)22-5/h2-7,15-20H,1H2,(H3,12,13,14)/t2-,3-,4-,5+,6-,7+,9+,10-,11+/m1/s1

4368-28-9 Relevant articles

Total Synthesis of (?)-Tetrodotoxin and 11-norTTX-6(R)-ol

Maehara, Tomoaki,Motoyama, Keisuke,Toma, Tatsuya,Yokoshima, Satoshi,Fukuyama, Tohru

supporting information, p. 1549 - 1552 (2017/02/05)

The enantioselective total synthesis of ...

An efficient total synthesis of optically active tetrodotoxin

Nishikawa, Toshio,Urabe, Daisuke,Isobe, Minoru

, p. 4782 - 4785 (2007/10/03)

The toxic principle of puffer-fish poiso...

First asymmetric total synthesis of tetrodotoxin

Ohyabu, Norio,Nishikawa, Toshio,Isobe, Minoru

, p. 8798 - 8805 (2007/10/03)

Tetrodotoxin, a toxic principle of puffe...

ISOLATION OF 11-OXOTETRODOTOXIN FROM THE PUFFER AROTHRON NIGROPUNCTATUS

Khora, Samanta S.,Yasumoto, Takeshi

, p. 4393 - 4394 (2007/10/02)

A novel tetrodotoxin analog was isolated...

4368-28-9 Process route

C<sub>28</sub>H<sub>49</sub>N<sub>3</sub>O<sub>12</sub>Si

C28 H49 N3 O12 Si

4,9-anhydrotetrodotoxin

4,9-anhydrotetrodotoxin

tetradotoxin
4368-28-9

tetradotoxin

Conditions
Conditions Yield
With trifluoroacetic acid; In water; at 20 ℃;
58%
36%
[(2R,5S,6R)-2-Benzyloxymethoxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-cyclohex-3-en-(E)-ylidene]-acetaldehyde
588693-73-6

[(2R,5S,6R)-2-Benzyloxymethoxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-cyclohex-3-en-(E)-ylidene]-acetaldehyde

tetradotoxin
4368-28-9

tetradotoxin

Conditions
Conditions Yield
Multi-step reaction with 34 steps
1.1: 2-methyl-2-butene; aq. NaH2 PO4 ; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C
2.1: 1.60 g / benzene; methanol / 1 h / 20 °C
3.1: CH2 Cl2 / 0.25 h / 0 °C
4.1: 1.68 g / K2 CO3 / methanol / 10 h / 0 °C
5.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C
6.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C
7.1: pyridine / 10 h / 50 °C
8.1: 2.15 g / Et3 N; DMAP / tetrahydrofuran / 48 h / 20 °C
9.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C
10.1: 98 percent / Na2 HPO4 ; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C
11.1: 95 percent / Et3 N / CH2 Cl2 / 0.67 h / -42 °C
12.1: Ac2 O; DMSO / 2 h / 20 °C
13.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C
14.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C
15.1: 89 percent / TFA / methanol / 3 h / 20 °C
16.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C
17.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C
18.1: NMO; OsO4 / acetone; H2 O / 3 h / 20 °C
19.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C
20.1: NaBH4 / methanol / 0.25 h / -78 °C
21.1: Et3 N; MeOH / 28.8 h / 15 °C
22.1: pyridine; Et3 N / CH2 Cl2 / 0.5 h / 0 °C
22.2: pyridine; DMAP / CH2 Cl2 / 2 h / 20 °C
23.1: Pd(OH)2/C / methanol / 12 h / 20 °C
24.1: 96 mg / DMAP / pyridine / 2 h / 20 °C
25.1: 75 percent / aq. TFA / methanol; H2 O / 26.4 h / 20 °C
26.1: CAN / acetonitrile; H2 O / 2 h / 85 °C
27.1: 38.5 mg / Et3 N; HgCl2 / dimethylformamide / 2 h / 20 °C
28.1: NaIO4 / methanol; H2 O / 0.5 h / 20 °C
29.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C
30.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C
31.1: HCl; dioxane / 24 h
32.1: 11.2 mg / Et3 N / pyridine / 12 h / 40 °C
33.1: 18 percent / Et3 N / aq. methanol / 8 h / 20 °C
34.1: 63 percent / trifluoroacetic acid; D2 O / 96 h
With pyridine; hydrogenchloride; methanol; dmap; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; 2-methyl-but-2-ene; ammonium cerium(IV) nitrate; potassium tert-butylate; acetic anhydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; mercury dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; hydrogenchloride; methanol; dichloromethane; water; water-d2; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; acetonitrile; trifluoroacetic acid; tert-butyl alcohol; benzene; 12.1: Albright-Goldman reaction;
Multi-step reaction with 35 steps
1.1: 2-methyl-2-butene; aq. NaH2 PO4 ; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C
2.1: 1.60 g / benzene; methanol / 1 h / 20 °C
3.1: CH2 Cl2 / 0.25 h / 0 °C
4.1: 1.68 g / K2 CO3 / methanol / 10 h / 0 °C
5.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C
6.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C
7.1: pyridine / 10 h / 50 °C
8.1: 2.15 g / Et3 N; DMAP / tetrahydrofuran / 48 h / 20 °C
9.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C
10.1: 98 percent / Na2 HPO4 ; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C
11.1: 95 percent / Et3 N / CH2 Cl2 / 0.67 h / -42 °C
12.1: Ac2 O; DMSO / 2 h / 20 °C
13.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C
14.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C
15.1: 89 percent / TFA / methanol / 3 h / 20 °C
16.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C
17.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C
18.1: NMO; OsO4 / acetone; H2 O / 3 h / 20 °C
19.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C
20.1: NaBH4 / methanol / 0.25 h / -78 °C
21.1: Et3 N; MeOH / 28.8 h / 15 °C
22.1: pyridine; Et3 N / CH2 Cl2 / 0.5 h / 0 °C
22.2: pyridine; DMAP / CH2 Cl2 / 2 h / 20 °C
23.1: Pd(OH)2/C / methanol / 12 h / 20 °C
24.1: 96 mg / DMAP / pyridine / 2 h / 20 °C
25.1: 75 percent / aq. TFA / methanol; H2 O / 26.4 h / 20 °C
26.1: CAN / acetonitrile; H2 O / 2 h / 85 °C
27.1: 38.5 mg / Et3 N; HgCl2 / dimethylformamide / 2 h / 20 °C
28.1: NaIO4 / methanol; H2 O / 0.5 h / 20 °C
29.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C
30.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C
31.1: HCl; dioxane / 24 h
32.1: 11.2 mg / Et3 N / pyridine / 12 h / 40 °C
33.1: 67 percent / Et3 N / aq. methanol / 8 h / 20 °C
34.1: 15 percent / trifluoroacetic acid; D2 O / 96 h
35.1: 63 percent / trifluoroacetic acid; D2 O / 96 h
With pyridine; hydrogenchloride; methanol; dmap; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; 2-methyl-but-2-ene; ammonium cerium(IV) nitrate; potassium tert-butylate; acetic anhydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; mercury dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; hydrogenchloride; methanol; dichloromethane; water; water-d2; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; acetonitrile; trifluoroacetic acid; tert-butyl alcohol; benzene; 12.1: Albright-Goldman reaction;
Multi-step reaction with 34 steps
1.1: 2-methyl-2-butene; aq. NaH2 PO4 ; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C
2.1: 1.60 g / benzene; methanol / 1 h / 20 °C
3.1: CH2 Cl2 / 0.25 h / 0 °C
4.1: 1.68 g / K2 CO3 / methanol / 10 h / 0 °C
5.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C
6.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C
7.1: pyridine / 10 h / 50 °C
8.1: 2.15 g / Et3 N; DMAP / tetrahydrofuran / 48 h / 20 °C
9.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C
10.1: 98 percent / Na2 HPO4 ; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C
11.1: 95 percent / Et3 N / CH2 Cl2 / 0.67 h / -42 °C
12.1: Ac2 O; DMSO / 2 h / 20 °C
13.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C
14.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C
15.1: 89 percent / TFA / methanol / 3 h / 20 °C
16.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C
17.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C
18.1: NMO; OsO4 / acetone; H2 O / 3 h / 20 °C
19.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C
20.1: NaBH4 / methanol / 0.25 h / -78 °C
21.1: Et3 N; MeOH / 28.8 h / 15 °C
22.1: pyridine; Et3 N / CH2 Cl2 / 0.5 h / 0 °C
22.2: pyridine; DMAP / CH2 Cl2 / 2 h / 20 °C
23.1: Pd(OH)2/C / methanol / 12 h / 20 °C
24.1: 96 mg / DMAP / pyridine / 2 h / 20 °C
25.1: 75 percent / aq. TFA / methanol; H2 O / 26.4 h / 20 °C
26.1: CAN / acetonitrile; H2 O / 2 h / 85 °C
27.1: 38.5 mg / Et3 N; HgCl2 / dimethylformamide / 2 h / 20 °C
28.1: NaIO4 / methanol; H2 O / 0.5 h / 20 °C
29.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C
30.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C
31.1: HCl; dioxane / 24 h
32.1: 11.2 mg / Et3 N / pyridine / 12 h / 40 °C
33.1: 67 percent / Et3 N / aq. methanol / 8 h / 20 °C
34.1: 66 percent / trifluoroacetic acid; D2 O / 96 h
With pyridine; hydrogenchloride; methanol; dmap; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; 2-methyl-but-2-ene; ammonium cerium(IV) nitrate; potassium tert-butylate; acetic anhydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; mercury dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; hydrogenchloride; methanol; dichloromethane; water; water-d2; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; acetonitrile; trifluoroacetic acid; tert-butyl alcohol; benzene; 12.1: Albright-Goldman reaction;

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