An indole alkaloid with analgesic activity
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Akuammine

Item No. 35149

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3E,7aS,12aS,12bS,15R)-3-ethylidene-1,3,4,6,7,12b-hexahydro-9-hydroxy-12-methyl-2H,12H-12a,2,7a-(epoxyethanylylidene)indolo[2,3-a]quinolizine-15-carboxylic acid, methyl ester
CAS Number
3512-87-6
Synonyms
  • (-)-Akuammine
  • Vincamajoridine
Molecular Formula
C22H26N2O4
Formula Weight
382.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 1 mg/ml
SMILES
COC([C@@]12[C@]34[C@](N(C5=CC=C(O)C=C54)C)(OC2)[C@](N(C/6)CC3)([H])C[C@H]1C6=C/C)=O
InChi Code
InChI=1S/C22H26N2O4/c1-4-13-11-24-8-7-21-16-9-14(25)5-6-17(16)23(2)22(21)18(24)10-15(13)20(21,12-28-22)19(26)27-3/h4-6,9,15,18,25H,7-8,10-12H2,1-3H3/b13-4-/t15-,18-,20-,21-,22+/m0/s1
InChi Key
YILKZADAWNUTTB-QLWRWLBVSA-N
Origin
Plant/Picralima nitida
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $128

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    5 mg

    $510

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    10 mg

    $887

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    Product Description

    Akuammine is an indole alkaloid that has been found in Picralima nitida and has analgesic activity.1 It selectively binds to the μ- and κ-opioid receptors over the δ-opioid receptor (Kis = 0.3, 1.68, and 10.4 µM for the human receptors, respectively). Akuammine inhibits forskolin-induced cAMP production in HEK293 cells expressing human μ- or κ-opioid receptors (IC50s = 2.6 and 0.073 µM, respectively). It increases the latency to withdrawal in the tail-flick or hot plate test in mice when administered at a dose of 60 mg/kg.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Creed, S.M., Gutridge, A.M., Argade, M.D., et al. Isolation and pharmacological characterization of six opioidergic Picralima nitida alkaloids. J. Nat. Prod. 84(1), 71-80 (2021).