Synonym
(+)-Laudanosine, (S)-Laudanosine, L-(+)-Laudanosine, L-Laudanosine
IUPAC/Chemical Name
(1S)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinoline
InChi Key
KGPAYJZAMGEDIQ-KRWDZBQOSA-N
InChi Code
InChI=1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m0/s1
SMILES Code
COC1=C(OC)C=C(CCN(C)[C@H]2CC3=CC=C(OC)C(OC)=C3)C2=C1
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
357.45
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. Fodale, V., and Santamaria, L.B. Laudanosine, an atracurium and cisatracurium metabolite. Eur. J. Anaesthesiol. 19(7), 466-473 (2002).
2. Siatka, T., Adamcová, M., Opletal, L., et al. Cholinesterase and prolyl oligopeptidase inhibitory activities of alkaloids from Argemone platyceras (Papaveraceae). Molecules 22(7), E1181 (2017).
3. Chia, Y.-C., Chang, F.-R., Wu, C.-C., et al. Effect of isoquinoline alkaloids of different structural types on antiplatelet aggregation in vitro. Planta Med. 72(13), 1238-1241 (2006).
4: Wu YJ, Chen JH, Teng MY, Li X, Jiang TY, Huang FR, Yao QJ, Shi BF. Cobalt-Catalyzed Enantioselective C-H Annulation of Benzylamines with Alkynes: Application to the Modular and Asymmetric Syntheses of Bioactive Molecules. J Am Chem Soc. 2023 Nov 15;145(45):24499-24505. doi: 10.1021/jacs.3c10714. Epub 2023 Nov 2. PMID: 38104268.
5: Dang TT, Facchini PJ. Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy. Plant Physiol. 2012 Jun;159(2):618-31. doi: 10.1104/pp.112.194886. Epub 2012 Apr 25. PMID: 22535422; PMCID: PMC3375929.
