A selective β3-AR agonist
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Small Molecule Modulators
Receptor Pharmacology
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SR 58611A (hydrochloride)

Item No. 11954

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
[[(7S)-7-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-5,6,7,8-tetrahydro-2-naphthalenyl]oxy]-acetic acid, ethyl ester, monohydrochloride
CAS Number
121524-09-2
Synonyms
  • Amibegron
Molecular Formula
C22H26ClNO4 • HCl
Formula Weight
440.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
277 nm
SMILES
CCOC(COC1=CC=C(CC[C@H](NC[C@H](O)C2=CC(Cl)=CC=C2)C3)C3=C1)=O.Cl
InChi Code
InChI=1S/C22H26ClNO4.ClH/c1-2-27-22(26)14-28-20-9-7-15-6-8-19(11-17(15)12-20)24-13-21(25)16-4-3-5-18(23)10-16;/h3-5,7,9-10,12,19,21,24-25H,2,6,8,11,13-14H2,1H3;1H/t19-,21-;/m0./s1
InChi Key
NQIZCDQCNYCVAS-RQBPZYBGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $66

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    5 mg

    $149

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    10 mg

    $264

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    Product Description

    SR 58611A is a selective β3-adrenergic receptor agonist (β3-AR; EC50 = 3.5 nM in rat colon).1 Its activity cannot be blocked by the β1- and β2-AR antagonists CGP 20712A and ICI 118551 (Item No. 15591), respectively. SR 58611A is minimally active against β1-ARs in rat uterus (EC50 = 499 nM) and inactive against β2-ARs in guinea pig trachea and atrium (EC50s = >10,000 and >30,000 nM, respectively). SR 58611A activates brown fat metabolism through activation of adenylyl cyclase activity and glycerol release in brown adipocytes (EC50s = 20 and 11 nM, respectively).2 It also reduces hypothermia produced by apomorphine (Item No. 16094) and reserpine (Item No. 16474) and potentiates toxicity produced by yohimbine (Item No. 19869) in mice.3 SR 58611A (0.6 to 2 mg/kg/day) also reduces the number of escape failures in a learned helplessness model of antidepressant-like activity in rats without changes in locomotor activity typically seen with β2-AR agonists.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bianchetti, A., and Manara, L. In vitro inhibition of intestinal motility by phenylethanolaminotetralines: Evidence of atypical β-adrenoceptors in rat colon. Br. J. Pharmacol. 100(4), 831-839 (1990).

    2. Nisoli, E., Tonello, C., and Carruba, M.O. SR 58611A: A novel thermogenic β-adrenoceptor agonist. Eur. J. Pharmacol. 259(2), 181-186 (1994).

    3. Simiand, J., Keane, P.E., Guitard, J., et al. Antidepressant profile in rodents of SR 58611A, a new selective agonist for atypical β-adrenoceptors. Eur. J. Pharmacol. 219(2), 193-201 (1992).