Synonym
Carnegine hydrochloride; NSC36664; NSC 36664; NSC-36664
IUPAC/Chemical Name
6,7-dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline hydrochloride
InChi Key
LARXMHOYLNCTFD-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H19NO2.ClH/c1-9-11-8-13(16-4)12(15-3)7-10(11)5-6-14(9)2;/h7-9H,5-6H2,1-4H3;1H
SMILES Code
COc1c(OC)cc2c(CCN(C2C)C)c1.Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
257.76
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Li X, Leonori D, Sheikh NS, Coldham I. Synthesis of 1-substituted tetrahydroisoquinolines by lithiation and electrophilic quenching guided by in situ IR and NMR spectroscopy and application to the synthesis of salsolidine, carnegine and laudanosine. Chemistry. 2013 Jun 10;19(24):7724-30. doi: 10.1002/chem.201301096. Epub 2013 May 15. PMID: 23677770.
2: Fogleman JC, Danielson PB, Frank MR. Comparison of Drosophila cytochrome P450 metabolism of natural and model substrates. J Insect Physiol. 1997 Oct;43(10):953-957. doi: 10.1016/s0022-1910(97)00038-3. PMID: 12770465.
3: Mezghani-Jarraya R, Hammami H, Ayadi A, Damak M. Molluscicidal activity of Hammada scoparia (Pomel) Iljin leaf extracts and the principal alkaloids isolated from them against Galba truncatula. Mem Inst Oswaldo Cruz. 2009 Nov;104(7):1035-8. doi: 10.1590/s0074-02762009000700017. PMID: 20027474.
4: Louafi F, Hurvois JP, Chibani A, Roisnel T. Synthesis of tetrahydroisoquinoline alkaloids via anodic cyanation as the key step. J Org Chem. 2010 Aug 20;75(16):5721-4. doi: 10.1021/jo100714y. PMID: 20704442.
5: Bembenek ME, Abell CW, Chrisey LA, Rozwadowska MD, Gessner W, Brossi A. Inhibition of monoamine oxidases A and B by simple isoquinoline alkaloids: racemic and optically active 1,2,3,4-tetrahydro-, 3,4-dihydro-, and fully aromatic isoquinolines. J Med Chem. 1990 Jan;33(1):147-52. doi: 10.1021/jm00163a025. PMID: 2296014.
6: El-Shazly A, Wink M. Tetrahydroisoquinoline and beta-carboline alkaloids from Haloxylon articulatum (Cav.) Bunge (Chenopodiaceae). Z Naturforsch C J Biosci. 2003 Jul-Aug;58(7-8):477-80. doi: 10.1515/znc-2003-7-805. PMID: 12939030.
7: Danielson PB, Frank MR, Fogleman JC. Comparison of larval and adult P-450 activity levels for alkaloid metabolism in desertDrosophila. J Chem Ecol. 1994 Aug;20(8):1893-906. doi: 10.1007/BF02066231. PMID: 24242717.
8: Erhardt PA, Soine TO. Stereochemical preferences for curarimimetic neuromuscular junction blockade I: enantiomeric monoquaternary amines as probes. J Pharm Sci. 1975 Jan;64(1):53-62. doi: 10.1002/jps.2600640110. PMID: 124343.
9: Naghaway JA, Soine TO. Hofmann elimination with diazomethane on curare bases and selected quaternary tetrahydroisoquinoline alkaloids. J Pharm Sci. 1978 Apr;67(4):473-7. doi: 10.1002/jps.2600670408. PMID: 641751.
10: Bruhn JG, Lundström J. Alkaloids of Carnegiea gigantea. Arizonine, a new tetrahydroisoquinoline alkaloid. Lloydia. 1976 Jul-Aug;39(4):197-203. PMID: 957908.
