Tetrahydropapaverine hydrochloride CAS#: 6429-04-5; ChemWhat Code: 81923
Identification
| Product Name | Tetrahydropapaverine hydrochloride |
| IUPAC Name | 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;hydrochloride |
| Molecular Structure |  |
| CAS Registry Number | 6429-04-5 |
| EINECS Number | No data available |
| MDL Number | No data available |
| Beilstein Registry Number | No data available |
| Synonyms | 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride, Tetrahydropapaverine hydrochloride, 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride, (+/-)-tetrahydropapaverine hydrochloride, (+/-)-N-norlaudanosine hydrochloride, (+/-)-norlaudanosine hydrochloride, tetrahydropapaverine hydrochloride;CAS No.: 6429-04-5; CAS Number: 6429-04-5 |
| Molecular Formula | C20H26ClNO4 |
| Molecular Weight | 379.8 |
| 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 |
| InChI Key | VMPLLPIDRGXFTQ-UHFFFAOYSA-N |
| Canonical SMILES | COc1ccc(cc1OC)CC2c3cc(c(cc3CCN2)OC)OC.Cl |
| Patent Information |
| No data available |
Physical Data
| Appearance | White powder |
| Solubility | No data available |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
| Melting Point, °C | Solvent (Melting Point) |
| 211 – 215 | |
| 216 | methanol, ethyl acetate |
| 217 – 219 | ethanol |
| 83 – 85 | H2O |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | water-d2 | 500 |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | 126 |
| Chemical shifts | 1H | D2O |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Comment (IR Spectroscopy) |
| Bands | nujol | 3100 – 1590 cm**(-1) |
Route of Synthesis (ROS)
| Conditions | Yield |
| With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 17h; Experimental Procedure 1-(1-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-2-(3,4-dimethoxyphenyl)ethanone (7) A mixture of 6•HCl (5.7 g, 15 mmol), homoveratric acid 10 (2.94 g, 15 mmol), HOBt (2.28 g, 16.8 mmol),EDC (3 mL, 16.8 mmol) and Et3N (6.3 mL, 45 mmol) in CH2Cl2 (300 mL) was stirred at room temperaturefor 17 h. The mixture was diluted with CH2Cl2 (100 mL) and was washed with 10% HCl (30 mL x 2), satdNaHCO3 (30 mL) and brine (30 mL), dried over Na2SO4, filtrated and evaporated to afford yellow solids.Recrystallization from EtOH (135 mL) gave amide 7 (6.96 g, 89%) as yellow solids of mp 148-150 °C.1H NMR (the ratio of rotamer is 66/34): 2.49-2.61 (1.32H, m), 2.70 (0.34H, m), 2.92 (0.34H, m), 2.93(0.66H, dd, J = 8.0, 13.2), 2.98 (0.34H, dd, J = 5.2, 13.7), 3.02 (0.34H, d, J = 16.0), 3.07 (0.34H, dd, J = 9.2,13.7), 3.10 (0.66H, dd, J = 5.8, 13.2), 3.19 (0.34H, m), 3.24 (0.34H, d, J = 16.0), 3.38 (0.66H, m), 3.61(1.98H, s), 3.67 (1.02H, s), 3.68-3.73 (1.98H, m), 3.75 (1.98H, s), 3.80 (1.98H, s), 3.83-3.84 (6H, m), 3.86(1.02H, s), 3.87 (3H, s), 3.88 (1.02H, s), 4.82 (0.34H, m), 4.92 (0.34H, dd, J = 5.2, 9.2), 5.67 (0.66H, dd, J= 5.8, 8.0), 6.18 (0.66H, s), 6.39 (0.34H, s), 6.43-6.45 (0.68H, m), 6.15-6.52 (1.32H, m), 6.62-6.80 (4.66H,m), 6.84 (0.34 H, d, J = 8.6). 13C NMR: 27.9 (CH2), 28.3 (CH2), 35.2 (CH2), 39.6 (CH2), 41.1 (CH2), 41.2(CH2), 41.8 (CH2), 42.4 (CH), 54.0 (CH), 56.6 (CH3), 55.8 (CH3), 55.93 (CH3), 55.96 (CH3), 55.99 (CH3), 56.1 (CH3), 58.6 (CH), 110.1 (CH), 110.82 (CH), 110.89 (CH), 110.93 (CH), 111.2 (CH), 111.4 (CH), 111.5(CH), 111.6 (CH), 111.8 (CH), 111.9 (CH), 112.8 (CH), 112.9 (CH), 120.8 (CH), 120.9 (CH), 121.9 (CH),122.1 (CH), 125.6 (C), 126.7 (C), 127.5 (C), 127.7 (C), 128.0 (C), 128.3 (C), 130.5 (C), 130.7 (C), 147.0(C), 147.4 (C), 147.69 (C), 147.72 (C), 147.9 (C), 148.2 (C), 148.3 (C), 148.9 (C), 145.1 (C), 170.1 (C),170.4 (C). IR: 1630. HRMS-ESI m/z: [M+Na]+ calcd for C30H35NNaO7, 544.2311; found, 544.2300. | 89% |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P264, P270, P301+P312, P330, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) For more detailed information, please visit ECHA C&L website |
| Source: European Chemicals Agency (ECHA) License Note: Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: “Source: European Chemicals Agency, http://echa.europa.eu/”. Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. License URL: https://echa.europa.eu/web/guest/legal-notice Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446 Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database |
Other Data
| Transportation | Not dangerous goods |
| Under the room temperature and away from light | |
| HS Code | 293349 |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 yearS |
| Market Price | USD |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 379.884 |
| logP | 3.255 |
| HBA | 1 |
| HBD | 1 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 48.95 |
| Rotatable Bond (RotB) | 6 |
| Matching Veber Rules | 2 |
| Use Pattern |
| Used as Atracurium intermediate. |
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