An indole alkaloid with analgesic activity
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Akuammidine

Item No. 35150

Product Insert (PDF)
Technical Information
Formal Name
17-hydroxy-sarpagan-16-carboxylic acid, methyl ester
CAS Number
639-36-1
Synonyms
  • Rhazine
Molecular Formula
C21H24N2O3
Formula Weight
352.4
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
COC([C@]1([C@]2([H])[N@]3[C@@H](C4=C(C5=CC=CC=C5N4)C2)C[C@@H]1/C(C3)=C\C)CO)=O
InChi Code
InChI=1S/C21H24N2O3/c1-3-12-10-23-17-9-15(12)21(11-24,20(25)26-2)18(23)8-14-13-6-4-5-7-16(13)22-19(14)17/h3-7,15,17-18,22,24H,8-11H2,1-2H3/b12-3-/t15-,17-,18-,21-/m1/s1
InChi Key
RCEFXZXHYFOPIE-QBICPXKZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $90

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    1 mg

    $153

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    Product Description

    Akuammidine is an indole alkaloid that has been found in P. nitida and has analgesic activity.1 It selectively binds to the μ-opioid receptor over the κ- and δ-opioid receptors (Kis = 0.32, 14.2, and 15 µM for the human receptors, respectively) and inhibits forskolin-induced cAMP production in HEK293 cells expressing the human μ-opioid receptor (IC50 = 3.14 µM). Akuammidine increases the latency to withdrawal in the tail-flick and hot plate tests in mice.

    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).