An anti-apoptotic antioxidant
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Enantiomer(s)
11981(S)-Pramipexole (hydrochloride)
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(R)-Pramipexole (hydrochloride)

Item No. 18234

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazolediamine, dihydrochloride
CAS Number
104632-27-1
Synonyms
  • Dexpramipexole
  • KNS 760704
  • (+)-Pramipexole
  • SND 919CL2X
Molecular Formula
C10H17N3S • 2HCl
Formula Weight
284.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 5 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
219, 264 nm
SMILES
CCCN[C@@H]1CCC(N=C(N)S2)=C2C1.Cl.Cl
InChi Code
InChI=1S/C10H17N3S.2ClH/c1-2-5-12-7-3-4-8-9(6-7)14-10(11)13-8;;/h7,12H,2-6H2,1H3,(H2,11,13);2*1H/t7-;;/m1../s1
InChi Key
QMNWXHSYPXQFSK-XCUBXKJBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $72

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    10 mg

    $134

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    25 mg

    $315

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    50 mg

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    Product Description

    (R)-Pramipexole is an enantiomer of pramipexole that is ~100-fold less active than the (S) form as a dopamine receptor agonist.1,2 For this reason, it can be used as a negative control for the (S) form in the study of dopamine receptors. Both isoforms are antioxidants that target mitochondria to prevent apoptosis.1,3,4,5 This cytoprotective effect of (R)-pramipexole, without dopaminergic side effects, suggests utility in amyotrophic lateral sclerosis.1,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Danzeisen, R., Schwalenstoecker, B., Gillardon, F., et al. Targeted antioxidative and neuroprotective properties of the dopamine agonist pramipexole and its nondopaminergic enantiomer SND919CL2x [(+)2-amino-4,5,6,7-tetrahydro-6-Lpropylamino-benzathiazole dihydrochloride]. JPET 316(1), 189-199 (2006).

    2. Chang, W.I., Weber, M., Breier, M.R., et al. Stereochemical and neuroanatomical selectivity of pramipexole effects on sensorimotor gating in rats. Brain Res. 1437, 69-76 (2012).

    3. Ferrari-Toninelli, G., Maccarinelli, G., Uberti, D., et al. Mitochondria-targeted antioxidant effects of S(−) and R(+) pramipexole. BMC Pharmacol. 10(2), 1-6 (2010).

    4. Abramova, N.A., Cassarino, D.S., Khan, S.M., et al. Inhibition by R(+) or S(−) pramipexole of caspase activation and cell death induced by methylpyridinium ion orβamyloid peptide in SH-SY5Y neuroblastoma. J. Neurosci. Res. 67(4), 494-500 (2002).

    5. Gu, M., Iravani, M.M., Cooper, J.M., et al. Pramipexole protects against apoptotic cell death by non-dopaminergic mechanisms. J. Neurochem. 91(5), 1075-1081 (2004).

    6. Cheah, B.C., and Kiernan, M.C. Dexpramipexole, the R(+) enantiomer of pramipexole, for the potential treatment of amyotrophic lateral sclerosis. IDrugs. 13(12), 911-920 (2010).