The (S) enantiomer of laudanosine
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(S)-Laudanosine

Item No. 27170

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinoline
CAS Number
2688-77-9
Synonyms
  • (+)-Laudanosine
  • L-Laudanosine
  • L-(+)-Laudanosine
  • NSC 35045
Molecular Formula
C21H27NO4
Formula Weight
357.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: slightly solubleEthanol: slightly solubleMethanol: slightly soluble
SMILES
COC1=C(OC)C=C(CCN(C)[C@H]2CC3=CC=C(OC)C(OC)=C3)C2=C1
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
InChi Key
KGPAYJZAMGEDIQ-KRWDZBQOSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $75

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    5 mg

    $351

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    Product Description

    (S)-Laudanosine is the (S) enantiomer of laudanosine, a metabolite of the neuromuscular blocking agents atracurium (Item No. 17796) and cisatracurium (Item No. 22959).1 (S)-Laudanosine is also an alkaloid that has been found in the prickly poppy A. platyceras.2 It inhibits prolyl endopeptidase with an IC50 value of 341 μM. (S)-Laudanosine (100 μM) inhibits both arachidonic acid- and collagen-induced aggregation in washed rabbit platelets.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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).