Tetrahydropapaverine hydrochloride
[CAS# 6429-04-5]

Identification

• Classification: Biochemical >> Inhibitor >> Metabolism >> Hydroxylase inhibitor
• Name: Tetrahydropapaverine hydrochloride
• Synonyms: 1-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride
• Molecular Formula: C₂₀H₂₅NO₄.HCl
• Molecular Weight: 379.88
• CAS Registry Number: 6429-04-5
• EC Number: 229-213-9
• SMILES: COC1=C(C=C(C=C1)CC2C3=CC(=C(C=C3CCN2)OC)OC)OC.Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Tetrahydropapaveline hydrochloride is a derivative of the alkaloid tetrahydropapaveline, known for its medicinal properties and applications. Tetrahydropapaveline hydrochloride belongs to a group of synthetic derivatives derived from the alkaloid papaverine, originally isolated from the opium poppy (Papaver somniferum). The compound was first synthesized by chemical modification of papaverine, involving hydrogenation of the double bond in the tetrahydroisoquinoline ring structure to produce tetrahydropapaveline. Subsequent chlorination and hydrochlorination steps form tetrahydropapaveline hydrochloride, a water-soluble salt suitable for medical use.

Tetrahydropapaveline hydrochloride has a variety of pharmacological actions: Like its parent compound papaverine, tetrahydropapaveline hydrochloride acts as a smooth muscle relaxant. It primarily acts on vascular smooth muscle, causing vasodilation and increased blood flow to the affected tissue. It is used to relieve spasms of various smooth muscle tissues, including those of the gastrointestinal tract and urinary system.

Uses of Tetrahydropapaverine HCl in Cardiology: It is effective in treating vasospastic disorders such as coronary artery spasm and peripheral vascular disease by relaxing constricted blood vessels and improving blood circulation. It can be used to relieve symptoms of angina, especially those caused by coronary artery spasm.

Tetrahydropapaverine HCl is used to relieve ureteral and bladder spasms, help pass kidney stones and ureteral stones, and facilitate catheter insertion. It is used to reduce spasms of smooth muscles in the gastrointestinal tract and relieve symptoms of irritable bowel syndrome and other functional gastrointestinal disorders.

Tetrahydropapaverine HCl is usually taken orally or intravenously under the supervision of a physician. Dosages vary depending on the condition being treated and the patient's response to treatment. It is important to adhere to the prescribed dosing regimen so that the best treatment effect can be achieved while minimizing potential side effects.

Common side effects of tetrahydropapaverine HCl include mild dizziness, headache, nausea, and flushing. In rare cases, allergic reactions or more serious adverse reactions, such as low blood pressure, may occur. Tetrahydropapaverine HCl should be used with caution in patients with cardiovascular disease or who require careful monitoring of their blood pressure.

Research continues to optimize the pharmacological properties of tetrahydropapaverine hydrochloride and explore its potential applications in other medical fields. Ongoing studies are aimed at elucidating its mechanism of action, improving formulation technology, and expanding its therapeutic indications.

References

1980. Tetrahydropapaveroline Inhibits Dopamine Uptake in Rat Brain Synaptosomes. Alcohol and Aldehyde Metabolizing Systems-IV.
DOI: 10.1007/978-1-4757-1419-7_84

2023. High-Throughput Searches for Natural Products as Aggregation Modulators of Amyloidogenic Proteins. New Tide of Natural Product Chemistry.
DOI: 10.1007/978-981-99-1714-3_15

2022. Biosynthesis of tetrahydropapaverine and semisynthesis of papaverine in yeast. Proceedings of the National Academy of Sciences of the United States of America, 119(32).
DOI: 10.1073/pnas.2205848119