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(±)-threo-Methylphenidate (hydrochloride)

Item No. 11639

Restricted Product (Schedule II)
Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Synonyms
Synonyms
  • DL-threo-Methylphenidate
  • NSC 169868
  • Ritalinic Acid methyl ester
Technical Information
Formal Name
(αR,2R)-rel-α-phenyl-2-piperidineacetic acid, methyl ester, monohydrochloride
CAS Number
23655-65-4
Molecular Formula
C14H19NO2 • HCl
Formula Weight
269.8
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 25 mg/mlPBS (pH 7.2): 25 mg/ml
SMILES
O=C(OC)[C@H](C1=CC=CC=C1)[C@@]2([H])CCCCN2.Cl
InChi Code
InChI=1S/C14H19NO2.ClH/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12;/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3;1H/t12-,13-;/m1./s1
InChi Key
JUMYIBMBTDDLNG-OJERSXHUSA-N
Regulatory Information
DEA Schedule
II
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    (±)-threo-Methylphenidate (a.k.a., Ritalin) is a schedule II drug in the United States commonly used as a psychostimulant for the treatment of attention-deficit hyperactivity disorder. It blocks dopamine and norepinephrine transporters as well as facilitates NMDA-receptor mediated synaptic transmission through σ1 receptors via PLC/PKC signaling.1 This interaction with the σ1 receptor has been suggested to underlie (±)-threo-methylphenidate’s considerable abuse potential and potential psychiatric side effects.1,2 This product is intended for forensic and biological research applications.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhang, C.L., Feng, Z.J., Liu, Y., et al. Methylphenidate enhances NMDA-receptor response in medial prefrontal cortex via sigma-1 receptor: A novel mechanism for methylphenidate action. PLoS One 7(12), (2012).

    2. Lakhan, S.E., and Kirchgessner, A. Prescription stimulants in individuals with and without attention deficit hyperactivity disorder: Misuse, cognitive impact, and adverse effects. Brain Behav. 2(5), 661-677 (2012).