An oxysterol and a negative allosteric modulator of GABAA receptors
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Cholesta-3,5-dien-7-one

Item No. 34320

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cholesta-3,5-diene-7-one
CAS Number
567-72-6
Synonyms
  • Δ3,5-Cholestadien-7-one
  • CSD
  • NSC 18180
  • NSC 134914
Molecular Formula
C27H42O
Formula Weight
382.6
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: 10 mg/ml
λmax
278 nm
SMILES
O=C1C=C2C=CCC[C@]2(C)[C@]3([H])[C@]1([H])[C@@](CC[C@]4([H])[C@@H](CCCC(C)C)C)([H])[C@]4(C)CC3
InChi Code
InChI=1S/C27H42O/c1-18(2)9-8-10-19(3)21-12-13-22-25-23(14-16-27(21,22)5)26(4)15-7-6-11-20(26)17-24(25)28/h6,11,17-19,21-23,25H,7-10,12-16H2,1-5H3/t19-,21-,22+,23+,25+,26+,27-/m1/s1
InChi Key
TTXJJFWWNDJDNR-CZRUWHASSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Cholesta-3,5-dien-7-one is an oxysterol and a negative allosteric modulator of GABAA receptors.1,2 It reduces GABA-induced currents in HEK cells expressing α1β1γ2 or α4β3γ2 subunit-containing GABAA receptors (IC50s = 1.5 and 1 µM, respectively).2 Cholesta-3,5-dien-7-one (500 nM) reduces GABA-induced depolarization of peptidergic and non-peptidergic nociceptors, C-LTMRs, and cold thermosensors in isolated mouse dorsal root ganglion (DRG) neurons. In vivo, cholesta-3,5-dien-7-one (2, 10, and 50 mg/kg) increases latency to nocifensive behaviors in the hot plate test in mice.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hahn, M., Tang, M., and Subbiah, M.T. Cholest-3,5-dien-7-one formation in peroxidized human plasma as an indicator of lipoprotein cholesterol peroxidation potential. Biochim. Biophys. Acta 1255(3), 341-343 (1995).

    2. Niu, C., Leavitt, L.S., Lin, Z., et al. Neuroactive type-A γ-aminobutyric acid receptor allosteric modulator steroids from the hypobranchial gland of marine mollusk, Conus geographus. J. Med. Chem. 64(10), 7033-7043 (2021).