Basic information
- CAS
2688-77-9- Standard SMILES
COc1ccc(C[C@H]2c3cc(OC)c(OC)cc3CCN2C)cc1OC- InChIKey
KGPAYJZAMGEDIQ-KRWDZBQOSA-N- Molecular formula
- C21H27NO4
- Average molar mass
- 357.4 g/mol
- Monoisotopic mass
- 357.19400834
Names & identifiers
- Preferred name
- Laudanosine
- IUPAC
- (1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
- English name
- laudanosine
- Molecular formula
- C21H27NO4
- Molecular weight
- 357.44
Names & synonyms
Show more names
Database identifiers
- CAS
2688-77-9- PubChem CID
- 73397
- DTXSID
DTXSID30878577- ChEMBL
CHEMBL1407、CHEMBL519894- ChEBI
CHEBI:6389- UNII
- DA7R5WVN48
- EC Number
- 220-253-2
- Nikkaji
- J14.884I
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 40.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 434
Physicochemical properties
- Melting point
- 89 ° · 89°
- alpha
- 16 · D16 +106° (c = 1.6 in 97% alc); D16 +130° (chloroform); D22 +52.2 ±1.3° (chloroform); D20 +82.5° (ethanol)
- Boiling point
- 490.07 °C · 490.07°C (rough estimate)
- Density
- 1.1729 · 1.1729 (rough estimate)
- refractive index
- 1.5614 · 1.5614 (estimate)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly, Sonicated)
- form
- White to Pale Beige
- pka
- 7.8 · 7.80±0.40(Predicted)
- color
- White to off-white
- FDA UNII
- 7 R5WVN48 · DA7R5WVN48
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
Safety & regulation
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
A class of drugs producing both physiological and psychological effects through a variety of mechanisms. They can be divided into specific agents, e.g., affecting an identifiable molecular mechanism unique to target cells bearing receptors for that agent, and nonspecific agents, those producing effects on different target cells and acting by diverse molecular mechanisms. Those with nonspecific mechanisms are generally further classed according to whether they produce behavioral depression or stimulation. Those with specific mechanisms are classed by locus of action or specific therapeutic use. (From Gilman AG, et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p252)
Applications
UsesLaudanosine 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.
Upstream & downstream products
Upstream raw materials
Suppliers27 total
Additional notes
DefinitionChEBI: Laudanosine is a member of isoquinolines.
Related reactions
Compound notes
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