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291919

Sigma-Aldrich

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

97%

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About This Item

Empirical Formula (Hill Notation):
C11H15NO2 · HCl
CAS Number:
2328-12-3
Molecular Weight:
229.70
Beilstein:
3634126
MDL number:
MFCD00012744
UNSPSC Code:
12352100
PubChem Substance ID:
24857546
NACRES:
NA.22

Assay

97%

form

solid

mp

260-265 °C (lit.)

solubility

soluble 25 mg/mL, clear, colorless (1N NaOH in methanol)

SMILES string

Cl.COc1cc2CCNCc2cc1OC

InChI

1S/C11H15NO2.ClH/c1-13-10-5-8-3-4-12-7-9(8)6-11(10)14-2;/h5-6,12H,3-4,7H2,1-2H3;1H

InChI key

SHOWAGCIRTUYNA-UHFFFAOYSA-N

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General description

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride is also referred as heliamine. It is an alkaloid isolated from mexican cereoid, Backebergia militaris.

Application

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride has been used as starting material for the synthesis of more complex isoquinolines and quinolizidines.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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E Glusa et al.
Die Pharmazie, 45(6), 408-410 (1990-06-01)
The synthesis of the title compounds starting from 2-Chlormethylbenzdioxan and Tetrahydroisochinolines is presented. Their actions on the platelet aggregation and the inhibition of alpha-adrenoceptors at the isolated rabbit aorta and the vas deferens of the guinea pig were investigated.
R Mata et al.
Journal of pharmaceutical sciences, 69(1), 94-95 (1980-01-01)
Backebergia militaris (Andot) Bravo ex Sánchez Mejorada yielded alkaloid crystals from a fractionated ethanol extract of only 20 g of plant material. The alkaloid was identified as heliamine (6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline) hydrochloride. A second alkaloid, 3,4-dimethoxy-beta-phenethylamine hydrochloride, was crystallized after preparative TLC
Heterocycles, 34, 1857-1857 (1992)
S A Barker et al.
Biochemical pharmacology, 30(17), 2461-2468 (1981-09-01)
Gas chromatographic/mass spectrometric data are presented which demonstrate the presence of 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (DHTIQ) as a normal constituent of rat brain. The level of DHTIQ was calculated to be 10.0 +/- 3.0 ng/g wet weight (+/- S.D., N = 9) of
Ken-ichi Umehara et al.
Drug metabolism and disposition: the biological fate of chemicals, 37(7), 1427-1433 (2009-04-11)
(-)-N-{2-[(R)-3-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)piperidino]ethyl}-4-fluorobenzamide (YM758), a novel "funny" If current channel (If channel) inhibitor, is developed as a treatment for stable angina and atrial fibrillation. In this study, the pharmacokinetic/pharmacodynamic (PK/PD) relationship after intravenous administration of YM758 to tachycardia-induced dogs was investigated and
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