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Trimetoquinol hydrochloride
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Name

Trimetoquinol hydrochloride

 EINECS 242-423-5
CAS No. 18559-59-6 Density 1.235g/cm3
PSA 80.18000 LogP 3.68390
Solubility N/A Melting Point N/A
Formula C19H23 N O5 . Cl H Boiling Point 533.3°Cat760mmHg
Molecular Weight 381.856 Flash Point 276.3°C
Transport Information N/A Appearance N/A
Safety Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion and subcutaneous routes. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx and HCl. Risk Codes N/A
Molecular Structure Molecular Structure of 18559-59-6 ((S)-1,2,3,4-tetrahydro-6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)isoquinolinium chloride) Hazard Symbols N/A
Synonyms

6,7-Isoquinolinediol,1,2,3,4-tetrahydro-1-(3,4,5-trimethoxybenzyl)-, hydrochloride, (-)- (8CI);6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-[(3,4,5-trimethoxyphenyl)methyl]-,hydrochloride, (1S)- (9CI); 6,7-Isoquinolinediol,1,2,3,4-tetrahydro-1-[(3,4,5-trimethoxyphenyl)methyl]-, hydrochloride, (S)-; (-)-Trimethoquinol;(-)-Trimetoquinol; AQL 208; Bentomex; Inolin; NSC 288748; Trimethoquinol;Trimetoquinol; Trimetoquinol hydrochloride; Triquinol; Vems; l-Trimetoquinol

Article Data 3

Trimetoquinol hydrochloride Synthetic route

(S)-6,7-Bis(benzyloxy)-1-<(3,4,5-trimethoxyphenyl)methyl>-1,2,3,4-tetrahydroisoquinoline hydrochloride

18559-59-6

(-)-Trimetoquinol hydrochloride

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 50℃; under 3040 Torr; for 16h;96%

(1S,1'S)-6,7-dibenzyloxy-2-(2-hydroxy-1-phenylethyl)-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

18559-59-6

(-)-Trimetoquinol hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol86%

(3S)-8,9-dibenzyloxy-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo-<2,3-a>isoquinoline

18559-59-6

(-)-Trimetoquinol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 86 percent / H2, 10percent HCl / 10percent Pd-C / ethanol
View Scheme
3840-30-0

5-(chloromethyl)-1,2,3-trimethoxybenzene

18559-59-6

(-)-Trimetoquinol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 86 percent / H2, 10percent HCl / 10percent Pd-C / ethanol
View Scheme

N-(2-nitrophenylsulfenyl)-β-(3-hydroxy-4-(methoxymethoxy)phenyl)ethylamine

A

18559-59-6

(-)-Trimetoquinol hydrochloride

B

(+)-Trimetoquinol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium sulfate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 80 °C / Inert atmosphere
2: hydrogenchloride / ethanol; water; dichloromethane / 24 h / 20 °C
View Scheme
65299-00-5

3-hydroxy-4-(methoxymethoxy)benzaldehyde

A

18559-59-6

(-)-Trimetoquinol hydrochloride

B

(+)-Trimetoquinol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: ammonium acetate / 1 h / Molecular sieve; Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux
3: triethylamine; potassium carbonate / water; chloroform; methanol / 2 h / 0 °C
4: magnesium sulfate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 80 °C / Inert atmosphere
5: hydrogenchloride / ethanol; water; dichloromethane / 24 h / 20 °C
View Scheme
139-85-5

3,4-dihydroxybenzaldehyde

A

18559-59-6

(-)-Trimetoquinol hydrochloride

B

(+)-Trimetoquinol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium carbonate / acetonitrile / 0.5 h / 20 °C
1.2: 2 h
2.1: ammonium acetate / 1 h / Molecular sieve; Reflux
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux
4.1: triethylamine; potassium carbonate / water; chloroform; methanol / 2 h / 0 °C
5.1: magnesium sulfate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 80 °C / Inert atmosphere
6.1: hydrogenchloride / ethanol; water; dichloromethane / 24 h / 20 °C
View Scheme

C27H30N2O8S

A

18559-59-6

(-)-Trimetoquinol hydrochloride

B

(+)-Trimetoquinol hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; dichloromethane; water at 20℃; for 24h; Overall yield = 86 %; Overall yield = 62 mg;

(E)-3-hydroxy-4-(methoxymethoxy)-1-(2-nitrovinyl)benzene

A

18559-59-6

(-)-Trimetoquinol hydrochloride

B

(+)-Trimetoquinol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux
2: triethylamine; potassium carbonate / water; chloroform; methanol / 2 h / 0 °C
3: magnesium sulfate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 80 °C / Inert atmosphere
4: hydrogenchloride / ethanol; water; dichloromethane / 24 h / 20 °C
View Scheme

β-(3-hydroxy-4-(methoxymethoxy)phenyl)ethylamine

A

18559-59-6

(-)-Trimetoquinol hydrochloride

B

(+)-Trimetoquinol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; potassium carbonate / water; chloroform; methanol / 2 h / 0 °C
2: magnesium sulfate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 80 °C / Inert atmosphere
3: hydrogenchloride / ethanol; water; dichloromethane / 24 h / 20 °C
View Scheme

Trimetoquinol hydrochloride Chemical Properties

Inolin is aslo named as  Tretoquinol HCL;(S)-1,2,3,4-tetrahydro-6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)isoquinolinium chloride;-)-Trimethoquinol;6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-[(3,4,5-trimethoxyphenyl)methyl]-, hydrochloride, (1S)- (9CI);6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-[(3,4,5-trimethoxyphenyl)methyl]-, hydrochloride, (S)-;AQL 208;Bentomex,and so on.

Molecular Formula: C19H24ClNO5
Molecular Weight: 381.85056
EINECS: 242-423-5

Trimetoquinol hydrochloride Toxicity Data With Reference

1.   

orl-rat TDLo:2 g/kg (7-14D preg):TER

   OYYAA2    Oyo Yakuri. Pharmacometrics. 2 (1968),383.
2.   

orl-rat LD50:2 g/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 24 (1982),2331.
3.   

ipr-rat LD50:298 mg/kg

   EJPHAZ    European Journal of Pharmacology. 5 (1968),303.
4.   

scu-rat LD50:1100 mg/kg

   EJPHAZ    European Journal of Pharmacology. 5 (1968),303.
5.   

ivn-rat LD50:164 mg/kg

   EJPHAZ    European Journal of Pharmacology. 5 (1968),303.
6.   

orl-mus LD50:2250 mg/kg

   NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),529.
7.   

ipr-mus LD50:370 mg/kg

   EJPHAZ    European Journal of Pharmacology. 5 (1968),303.
8.   

scu-mus LD50:2000 mg/kg

   EJPHAZ    European Journal of Pharmacology. 5 (1968),303.
9.   

ivn-mus LD50:120 mg/kg

   NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),529.
10.   

ivn-dog LD50:160 mg/kg

   EJPHAZ    European Journ

RTECS:  NX0500000

Trimetoquinol hydrochloride Safety Profile

Inolin is poisonous by intravenous and intraperitoneal routes. Moderately toxic by ingestion and subcutaneous routes. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx and HCl.
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