Laudanosine

HCID 73397

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

N-MethyltetrahydropapaverineDA7R5WVN48NSC-35045RefChem:924552216-923-9220-253-21-((3,4-dimethoxyphenyl)methyl)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolineLaudanosine(S)-Laudanosine2688-77-9(+)-LaudanosineNSC 35045
Show more names
(+)-(S)-LaudanosineCisatracurium Besylate Impurity 49Atracurium Impurity 10(S-Laudanosine)(1S)-1,2,3,4-Tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinoline[1S,(+)]-1-[(3,4-Dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline
EINECS 220-253-2(1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline(1S)-1-[(3,4-Dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinoline(1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline(S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolineIsoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (1S)-(S)-(+)-LaudanosineAC1L2JSD

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

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

Safety & regulation

Safety data

Signal word
Danger
Symbol(GHS)
GHS06

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

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.

Suppliers27 total

广州隽唐科技有限公司020-36607679 13502246435 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
United Life Science020-82099279 18988941402 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]

Additional notes

DefinitionChEBI: Laudanosine is a member of isoquinolines.

Related reactions

1 records

Compound notes

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