DL-Laudanosine

• CAS: 1699-51-0
• Catalog Number: ACM1699510
• Category: Main Products
• Molecular Weight: 357.44
• Molecular Formula: C₂₁H₂₇NO₄
• Synonyms: N-Methyltetrahydropapaverine
• IUPAC Name: 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC
• InChI Key: KGPAYJZAMGEDIQ-UHFFFAOYSA-N
• Melting Point: 115 °C
• Appearance: white powder
• EC Number: 216-923-9
• Exact Mass: 357.19400
• Safety Description: 22-24/25

Case Study

Alkaloids Such as (±)-Laudanosine Can Be Synthesized Through the Stevens Rearrangement of Nitrile-Stabilized Ammonium Ylides

Orejarena Pacheco, et al. The Journal of Organic Chemistry, 2013, 78(10), 4985-4992.

The combined process of Stevens rearrangement of nitrile-stabilized ammonium ylides with subsequent reductive removal of the nitrile group allows easy synthesis of α-branched amines starting from α-aminonitriles. Through this reaction sequence researchers can synthesize multiple alkaloids such as (±)-laudanosine starting from two easily obtainable bicyclic α-aminonitriles.
General Procedure for the Stevens Rearrangement and Reductive Decyanation
· The reaction began by adding a KHMDS solution (56 mg, 0.28 mmol) in dry THF (1 mL) to a stirred isoquinolinium salt 11a suspension (120 mg, 0.259 mmol) in dry THF (7 mL) maintained at 0 °C.
· Following 1.5 to 3 hours of stirring at this temperature, then added EtOH (1 mL) and NaCNBH3 (57 mg, 0.91 mmol) to the mixture which then warmed to room temperature. The reaction mixture received acetic acid in a dropwise fashion using 85 µL of the compound which amounted to 1.5 mmol before stirring for 14 hours.
· Afterward, saturated aqueous NaHCO3 (15 mL) was added to the mixture and the product was extracted three times with 20 mL CH2Cl2 each time. Washed the combined organic phases with brine before drying them with Na2SO4 and concentrating them under reduced pressure. The purification of (±)-laudanosine (4a) through recrystallization using ethanol produced 77 mg of 4a which appeared as a white solid with an 83% yield.

Oxidative Cyclization of Laudanosine to Glaucine and Optimization of Conditions

Bali Judicaël Tra, Bi, et al. European Journal of Organic Chemistry, 2022, 2022(22), e202200301.

The oxidative cyclization of laudanosine (6) to glaucine (13) mediated by hypervalent iodine(III) has been documented multiple times in batch processes, typically using PhI(OCOCF3)2 as the oxidizing agent along with BF3·Et2O in CH2Cl2 at low temperatures, approximately -20 to -40 °C. However, even under similar conditions, the yields varied significantly, ranging from 33% to 75%, highlighting a reproducibility problem.
To establish a stable flow process at room temperature, this study utilized a dual-flow platform with an injection loop for reagent delivery. The composition of the solutions in loops 1 and 2 significantly influenced the results. When loop 1 was supplied with a solution of laudanosine (6) and loop 2 with a mixture of PIFA and BF3·Et2O, the conversion fell to 73% (entry 4). In contrast, using a mixture of laudanosine (6) and BF3·Et2O in the first stream while introducing PIFA in the second stream resulted in complete consumption of (6) and an 82% isolated yield of glaucine (13) (entry 5). Moreover, omitting either BF3·Et2O or PIFA did not produce glaucine (13) (entries 6-7).

Effects of Laudanosine on Respiratory Activity in Isolated Brainstem-Spinal Cord Preparations of Neonatal Rats

Sakuraba, Shigeki, et al. New Frontiers in Respiratory Control. Advances in Experimental Medicine and Biology, 2009, 669, 177-180.

The neuromuscular blocker atracurium degradates into laudanosine which passes through the blood-brain barrier and becomes epileptogenic when present in high concentrations. Laudanosine demonstrates dual regulatory actions on nicotinic acetylcholine receptors (nAChRs) which vary from activation to inhibition based on its concentration levels. The researchers used isolated brainstem-spinal cord preparations from neonatal rats to study how laudanosine affects central respiratory function.
· Methods
The respiratory rate was measured by recording rhythmic inspiratory burst activity from the C4 spinal cord ventral root using a glass inspiratory electrode. The preparations received perfusions of simulated CSF with concentrations of 1 μM, 10 μM or 100 μM laudanosine for a duration of 60 minutes.
· Results
Exposure to 1 μM, 10 μM and 100 μM laudanosine concentrations (each tested in 10 samples) failed to affect the C4 respiratory rate. The concentration of laudansine at 100 μM caused nonrespiratory excitatory activity in all 10 preparations which might match the epileptic seizures seen in vivo studies.

Custom Q&A

What is the molecular formula of 5',8-Dimethoxylaudanosine hydrochloride?

The molecular formula is C21H27NO4.

What are some synonyms for 5',8-Dimethoxylaudanosine hydrochloride?

Some synonyms are Laudanosine, DL-Laudanosine, and (+-)-Laudanosine.

What is the chemical safety profile of 5',8-Dimethoxylaudanosine hydrochloride?

The chemical safety profile is not specified in the reference.

What is the structure of 5',8-Dimethoxylaudanosine hydrochloride?

The structure is not depicted in the reference.

What is the CAS number for 5',8-Dimethoxylaudanosine hydrochloride?

The CAS number is 1699-51-0.

What is the EINECS number for 5',8-Dimethoxylaudanosine hydrochloride?

The EINECS number is 216-923-9.

What is the SMILES notation for 5',8-Dimethoxylaudanosine hydrochloride?

The SMILES notation is not given in the reference.

What is the PubChem CID for 5',8-Dimethoxylaudanosine hydrochloride?

The PubChem CID is not specified.

How many structural isomers are mentioned in the reference for 5',8-Dimethoxylaudanosine hydrochloride?

It is not mentioned how many structural isomers are present.

What are some other compounds with similar chemical structures to 5',8-Dimethoxylaudanosine hydrochloride?

Some similar compounds include Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- and Isoquinoline, 2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl-.