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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/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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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
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.
Heterocycles, 34, 1857-1857 (1992)
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
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
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