15052-05-8

Basic information

• Product Name: 1,3-Dioxolo[4,5-g]isoquinoline,5,6,7,8-tetrahydro-, hydrochloride (1:1)
• Synonyms: 1,3-Dioxolo[4,5-g]isoquinoline,5,6,7,8-tetrahydro-, hydrochloride (1:1);5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin;TDIQ (hydrochloride);5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline hydrochloride
• CAS NO: 15052-05-8
• Molecular Formula: C₁₀H₁₁NO₂*ClH
• Molecular Weight: 213.66078
• Mol File: 15052-05-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 319.2oC at 760 mmHg
• Flash Point: 121.1oC
• Appearance: /
• Vapor Pressure: 0.000345mmHg at 25°C
• CAS DataBase Reference: 1,3-Dioxolo[4,5-g]isoquinoline,5,6,7,8-tetrahydro-, hydrochloride (1:1)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxolo[4,5-g]isoquinoline,5,6,7,8-tetrahydro-, hydrochloride (1:1)(15052-05-8)
• EPA Substance Registry System: 1,3-Dioxolo[4,5-g]isoquinoline,5,6,7,8-tetrahydro-, hydrochloride (1:1)(15052-05-8)

Safety Data

• Hazardous Substances Data: 15052-05-8(Hazardous Substances Data)

Usage

Description

1,3-Dioxolo[4,5-g]isoquinoline,5,6,7,8-tetrahydro-, hydrochloride (1:1), also known as TDIQ (hydrochloride), is an analytical reference standard classified as a phenylalkylamine. It is structurally related to amphetamines but does not significantly impact locomotor activity. TDIQ is a partial agonist of α2A-, α2B-, and α2C-adrenergic receptors, with Kis values of 75, 95, and 65 nM, respectively. It has low affinity for dopamine or serotonin receptors and does not affect catecholamine release in rodent brain synaptosomes. TDIQ is used for forensic and research purposes.

Uses

Used in Pharmaceutical Synthesis:
1,3-Dioxolo[4,5-g]isoquinoline,5,6,7,8-tetrahydro-, hydrochloride (1:1) is used as an intermediate in the synthesis of (+/-)-β-Hydrastine (H675690), an inhibitor of dopamine biosynthesis.
Used in Research and Development:
In the field of neuroscience and pharmacology, TDIQ (hydrochloride) is used as a research compound to study its interactions with adrenergic receptors and its potential effects on anxiety and appetite in rodent models. It serves as a discriminative stimulus, generalizing to substances like cocaine and partially to 3,4-MDMA and methcathinone, but not to amphetamine.
Used in Forensic Analysis:
TDIQ (hydrochloride) is utilized in forensic analysis to identify and analyze substances related to its chemical structure, particularly in cases involving the examination of drugs and their metabolites.

InChI:InChI=1/C10H11NO2.ClH/c1-2-11-5-8-4-10-9(3-7(1)8)12-6-13-10;/h3-4,11H,1-2,5-6H2;1H

Synthetic route

hydrochloride of homopiperonylamine → 5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline; hydrochloride (15052-05-8)

formaldehyd (50-00-0) + hydrochloride of homopiperonylamine → 5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline; hydrochloride (15052-05-8)

Conditions	Yield
at 130℃; im Rohr;

Bis(7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6(5H)-yl)methane → 5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline; hydrochloride (15052-05-8)

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol at 20℃; for 18h;

formaldehyd (50-00-0) + 5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline; hydrochloride (15052-05-8) + butanone (78-93-3) → 4-(7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl)-3-methyl-butan-2-one

Conditions	Yield
In water

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline; hydrochloride (15052-05-8) + 2-nitrobenzyl chloride (610-14-0) + KOH-solution → 2-<2-nitro-benzoyl>-norhydrohydrastinine

formaldehyd (50-00-0) + 5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline; hydrochloride (15052-05-8) → hydrochloride of hydrohydrastinine

Conditions	Yield
at 130℃;

Upstream product

• 50-00-0 formaldehyd 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF SUBSTITUTED-1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES

The present invention is directed to a process for the synthesis of substituted-1,2,3,4-tetrahydroisoquinoline derivatives, useful as intermediates in the synthesis of pharmaceutical agents.