A benzyltetrahydroisoquinoline alkaloid with diverse biological activities
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(S)-Reticuline

Item No. 42219

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol
CAS Number
485-19-8
Synonyms
  • Reticuline
  • (+)-Reticuline
  • D-Reticuline
Molecular Formula
C19H23NO4
Formula Weight
329.4
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly soluble: 0.1-1 mg/ml
SMILES
COC(C=C(CCN1C)C([C@@H]1CC2=CC(O)=C(C=C2)OC)=C3)=C3O
InChi Code
InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1
InChi Key
BHLYRWXGMIUIHG-HNNXBMFYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $105

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    5 mg

    $471

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    Cayman Chemical
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    Product Description

    (S)-Reticuline is a benzyltetrahydroisoquinoline alkaloid that has been found in P. somniferum and has diverse biological activities.1,2,3,4,5 It inhibits acetylcholinesterase (AChE) and butyrylcholinesterase (BChE; IC50s = 301.01 and 65.04 µM, respectively).2 (S)-Reticuline (100 µM) inhibits the aggregation of washed isolated rabbit platelets induced by platelet-activating factor (PAF), collagen, or arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607).3 It also inhibits barium currents (IBa) in A7r5 rat embryonic thoracic aorta cells (IC50 = 39.6 µM) and prevents calcium chloride-induced contractions in isolated rat aortic rings.4 (S)-Reticuline (0.25 mg/kg) decreases airway resistance and bronchoalveolar lavage fluid (BALF) neutrophil, eosinophil, and lymphocyte infiltration in a mouse model of obesity-associated asthma induced by a high-fat diet and house dust mite (D. farinae) extracts.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brochmann-Hanssen, E., and Nielsen, B. (+)-Reticuline--a new opium alkaloid. Tetrahedron Lett. 18, 1271-1274 (1965).

    2. Wan Othman, W.N.N., Liew, S.Y., Khaw, K.Y., et al. Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae). Bioorg. Med. Chem. (18), 4464-4469 (2016).

    3. Chen, J.-J., Chang, Y.-L., Teng, C.-M., et al. Anti-platelet aggregation alkaloids and lignans from Hernandia nymphaeifolia. Planta Med. 66(3), 251-256 (1999).

    4. Medeiros, M.A., Nunes, X.P., Barbosa-Filho, J.M., et al. (S)-reticuline induces vasorelaxation through the blockade of L-type Ca2+ channels. Naunyn Schmiedebergs Arch Pharmacol. 379(2), 115-125 (2008).

    5. Lyu, X., Liu, J., Liu, Z., et al. Anti-inflammatory effects of reticuline on the JAK2/STAT3/SOCS3 and p38 MAPK/NF-κB signaling pathway in a mouse model of obesity-associated asthma. Clin. Respir. J. 18(1), (2024).