Tetrahydropapaverine hydrochloride Chemical Properties

Melting point:

216.0 to 220.0 °C

storage temp. 

Sealed in dry,2-8°C

Water Solubility 

Soluble in water

solubility 

Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly)

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C20H25NO4.ClH/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16;/h5-6,10-12,16,21H,7-9H2,1-4H3;1H

InChIKey

VMPLLPIDRGXFTQ-UHFFFAOYSA-N

SMILES

C12C=C(C(OC)=CC=1CCNC2CC1=CC=C(OC)C(OC)=C1)OC.Cl

CAS DataBase Reference

6429-04-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xn

Risk Statements 

22

Safety Statements 

36

RTECS 

NX5070700

HS Code 

29334900

Tetrahydropapaverine hydrochloride Usage And Synthesis

Uses

Tetrahydropapaverine hydrochloride is an organic amine compound that can be used as atracuramide intermediate.

Biological Activity

Tetrahydropapaverine (Norlaudanosine), a TIQs, is an analogue of Salsolinol and Tetrahydropapaveroline, and has neurotoxic effects on dopamine neurons.

Synthesis

Crude 3,4-dihydroisoquinoline hydrochloride 12 (6.48 g) was suspended in methanol (50 mL) under argon protection and cooled to 0 °C. Sodium borohydride (0.8 g, 21 mmol) was slowly added to this suspension. The reaction mixture was stirred at room temperature for 10 minutes and then concentrated. Subsequently, brine (16 mL) and acetonitrile (30 mL) were added to the concentrate and the mixture was then partitioned between ethyl acetate (30 mL) and water (30 mL). The aqueous layer was extracted twice with a solvent mixture of ethyl acetate-acetonitrile (30 mL, 1:1). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated to give a yellow oil. This oily substance was dissolved in methanol (10 mL), 5% hydrochloric acid solution in methanol (20 mL) was added and concentrated again. The residue was crystallized by the addition of ether, and the solid was collected by filtration and washed with ether to give finally 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (6-HCl, 4.67 g, 89% yield, after a 3-step reaction) as a white solid with a melting point of 211-215 °C. The 1H NMR (DMSO-d6) data were as follows: δ 2.91 (1H, m), 3.16-3.24 (3H, m), 3.36 (1H, m), 3.56 (1H, m), 3.60 (3H, s), 3.80 (3H, s), 3.85 (6H, s), 4.73 (1H, m), 6.17 (1H, s), 6.58 ( 1H, s), 6.72 (1H, d, J = 8.0 Hz), 6.77-6.79 (2H, m), 9.77 (1H, br s), 10.35 (1H, br s). The 1H NMR (D2O) data were as follows: δ 3.01-3.05 (2H, m), 3.16-3.29 (2H, m), 3.41 (1H, m), 3.53 (1H, m), 3.60 (3H, s), 3.72 (3H, s), 3.83 (6H, s), 4.73 (1H, m), 6.36 (1H, s), 6.73 ( 1H, s), 6.83-6.89 (2H, m), 7.00 (1H, m).

References

[1] Heterocycles, 2014, vol. 8, # 2, p. 1311 - 1321

Tetrahydropapaverine hydrochloride(6429-04-5)Related Product Information

• Triethylamine hydrochloride
• Diphenyldimethoxysilane
• D-Glucosamine hydrochloride
• Methoxyammonium chloride
• Dimethyldimethoxysilane
• Papaverine hydrochloride
• (+/-)-Tetrahydropapaverine
• DL-Carnitine
• L-Carnitine hydrochloride
• 1,1-Dimethoxyethane
• Isoquinoline
• Benzyl chloride
• N,N-Dimethylbenzylamine
• Topotecan hydrochloride
• Benzyltriethylammonium chloride
• Pyridine hydrochloride
• PAPAVERINE
• BOLDINE DIMETHYL ETHER