CAS 2688-77-9

laudanosine

Description:

Laudanosine is an alkaloid primarily derived from the opium poppy, specifically found in the plant's latex. It is classified as a tertiary amine and is known for its structural similarity to other opiate compounds. The chemical formula of laudanosine is C18H23NO3, and it features a complex bicyclic structure that contributes to its pharmacological properties. This compound is notable for its role as a metabolite of certain opioids and has been studied for its potential effects on the central nervous system. Laudanosine exhibits both stimulant and sedative properties, depending on the dosage and context of use. It is also recognized for its potential to induce respiratory depression, which is a significant concern in clinical settings. Due to its pharmacological activity, laudanosine is of interest in research related to pain management and anesthesia, although its use is limited compared to more commonly known opioids. Safety and toxicity profiles are critical considerations when studying this compound, particularly in relation to its effects on human health.

Formula: C₂₁H₂₇NO₄

InChI: InChI=1/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

InChI key: InChIKey=KGPAYJZAMGEDIQ-KRWDZBQOSA-N

SMILES: C([C@H]1C=2C(=CC(OC)=C(OC)C2)CCN1C)C3=CC(OC)=C(OC)C=C3

Synonyms:

• (1S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• (1S)-1-[(3,4-Dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline
• (S)-(+)-Laudanosine
• 1-(3,4-Dimethoxybenzyl)-6,7-Dimethoxy-2-Methyl-1,2,3,4-Tetrahydroisoquinoline
• <span class="text-smallcaps">L</span>-(+)-Laudanosine
• DL-6,7-dimethoxy-1-((3,4-dimethoxyphenyl)methyl)-2-methylisoquinoline
• DL-laudanosine
• Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (1S)-
• Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (S)-
• NSC 35045
• O-Methylcodamine
• Laudanosine
• Einecs 220-253-2
• (1S)-1,2,3,4-Tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline
• Cisatracurium Besylate Impurity 49

(S)-Laudanosine

CAS: 2688-77-9

(S)-Laudanosine

Purity: ≥98%

Molecular weight: 357.44g/mol

Ref: 54-BUP20265

Laudanosine

CAS: 2688-77-9

Formula: C₂₁H₂₇NO₄

Color and Shape: Pale Yellow Solid

Molecular weight: 357.45

Ref: 4Z-A-7531

(S)-Laudanosine

CAS: 2688-77-9

(S)-Laudanosine is the corresponding isomer of Laudanosine, which crosses the blood-brain barrier, with potential systemic toxicity and analgesic effects.

Formula: C₂₁H₂₇NO₄

Purity: 99.86%

Color and Shape: Solid

Molecular weight: 357.44

Ref: TM-TN7543

(S)-Laudanosine

Controlled Product

CAS: 2688-77-9

Applications Laudanosine is a metabolite of the neuromuscular-blocking drugs Atracurium (A794500) and Cisatracurium (C496700) with potentially toxic systemic effects. It crosses the blood-brain barrier and may cause excitement and seizure activity.
References Canfell, P., et al.: Drug Metab. Dispos., 14, 703 (1986), Anselmi, E., et al.: J. Pharm. Pharmacol., 44, 337 (1992), Bohrer, H., et al.: Pharmacol. Toxicol., 73, 137 (1993),

Formula: C₂₁H₂₇NO₄

Color and Shape: Neat

Molecular weight: 357.44

Ref: TR-L178525

Laudanosine

CAS: 2688-77-9

Formula: C₂₁H₂₇NO₄

Molecular weight: 357.45

Ref: ST-EA-CP-A131069

(S)-Laudanosine

CAS: 2688-77-9

Laudanosine is a gamma-aminobutyric acid (GABA) analog that is metabolized by the liver to form laudanosine. Laudanosine has been shown to be a competitive antagonist of benzodiazepine binding sites, including those of atracurium, mivacurium chloride, and diazepam. Laudanosine has also been shown to inhibit cyclic nucleotide phosphodiesterases in vitro, with clinical relevance for its use as an anti-epileptic drug.

Formula: C₂₁H₂₇NO₄

Purity: Min. 95%

Molecular weight: 357.44 g/mol

Ref: 3D-FL24858