An ACh uptake inhibitor and neuromuscular blocking agent
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(±)-Vesamicol (hydrochloride)

Item No. 43150

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,2R)-rel-2-(4-phenyl-1-piperidinyl)-cyclohexanol, monohydrochloride
CAS Number
120447-62-3
Synonyms
  • (±)-AH5183
  • trans-Vesamicol
Molecular Formula
C17H25NO • HCl
Formula Weight
295.9
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly soluble: 0.1-1 mg/mlEthanol: Sparingly soluble: 1-10 mg/mlPBS (pH 7.2): Sparingly soluble: 1-10 mg/ml
SMILES
O[C@@H]1CCCC[C@H]1N2CCC(CC2)C3=CC=CC=C3.Cl
InChi Code
InChI=1S/C17H25NO.ClH/c19-17-9-5-4-8-16(17)18-12-10-15(11-13-18)14-6-2-1-3-7-14;/h1-3,6-7,15-17,19H,4-5,8-13H2;1H/t16-,17-;/m1./s1
InChi Key
XJNUHVMJVWOYCW-GBNZRNLASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $74

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    10 mg

    $112

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    25 mg

    $222

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    50 mg

    $295

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    Product Description

    (±)-Vesamicol is an acetylcholine (ACh) uptake inhibitor (IC50 = 40 nM) and neuromuscular blocking agent.1,2 It binds to the vesamicol receptor (Ki = 2 nM), as well as sigma non-opioid intracellular receptor 1 (σ1-receptor) and sigma intracellular receptor 2 (σ2-receptor; Kis = 26 and 34 nM, respectively).3 (±)-Vesamicol (150 µg/kg) inhibits electrically induced maximal twitches of tibialis anterior muscles in anesthetized cats.2 It induces transient flaccid paralysis in conscious mice when administered intravenously or orally (ED50s = 2.7 and 35.5 mg/kg, respectively). Intracerebroventricular administration of (±)-vesamicol (80 or 100 µg/animal) decreases rapid eye movement (REM) sleep frequency and duration in rats.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rogers, G.A., Parsons, S.M., Anderson, D.C., et al. Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogues of trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol). J. Med. Chem. 32(6), 1217-1230 (1989).

    2. Brittain, R.T., Levy, G.P., and Tyers, M.B. The neuromuscular blocking action of 2-(4-phenylpiperidino) cyclohexanol (AH 5183). Eur. J. Pharm. 8(1), 93-99 (1969).

    3. Efange, S.M., Mach, R.H., Smith, C.R., et al. Vesamicol analogues as sigma ligands. Molecular determinants of selectivity at the vesamicol receptor. Biochem. Pharmacol. 49(6), 791-797 (1995).

    4. Salin-Pascual, R.J., and Jimenez-Anguiano, A. Vesamicol, an acetylcholine uptake blocker in presynaptic vesicles, suppresses rapid eye movement (REM) sleep in the rat. Psychopharmacology (Berl.) 121(4), 485-487 (1995).