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PRODUCT INFORMATION Dextrorphan-d3 (tartrate) Item No. 15810

CAS Registry No.: 1426174-16-4 D D Formal Name: (9α,13α,14α)-17-(methyl-d3)-morphinan- 3-ol 2R,3R-dihydroxybutanedioate N D

Synonym: d-3-hydroxy-N-Methylmorphinan H tartrate-d 3 • C4H6O6 MF: C17H20D3NO • C4H6O6 FW: 410.5 Purity: ≥98% Supplied as: A neat solid HO Storage: -20°C Stability: ≥4 years Information represents the product specifications. Batch specific analytical results are provided on each certificate of analysis.

Description

Dextrorphan-d3 (tartrate) (Item No. 15810) is intended for use as an internal standard for the quantification of dextrorphan tartrate (Item No. 15886) by GC- or LC-MS. The accuracy of the sample weight in this vial is between 5% over and 2% under the amount shown on the vial. If better precision is required, the deuterated standard should be quantitated against a more precisely weighed unlabeled standard by constructing a standard curve of peak intensity ratios (deuterated versus unlabeled). Dextrorphan is categorized as an arylcyclohexylamine and is a metabolite of dextromethorphan (hydrobromide hydrate) (Item No. 13950), an antitussive found in cough medicines. Dextrorphan, while also having antitussive activity, is psychoactive, leading to the abuse of cough medicines containing the parent 1,2 compound. Dextrorphan antagonizes NMDA and µ-opioid receptors (Kis = 54 and 420 nM, respectively) 3-5 and inhibits norepinephrine and serotonin transporters (Kis = 340 and 401 nM, respectively). This product is intended for research and forensic applications. This product is qualified as a Reference Material that has been manufactured and tested to ISO/IEC 17025 and ISO 17034 international standards for reference materials.

References

1. Shin, E.J., Lee, P.H., Kim, H.J., et al. Neuropsychotoxicity of abused drugs: Potential of dextromethorphan and novel neuroprotective analogs of dextromethorphan with improved safety profiles in terms of abuse and neuroprotective effects. J. Pharmacol. Sci. 106(1), 22-27 (2008). 2. Chomchai, C. and Manaboriboon, B. Stimulant methamphetamine and dextromethorphan use among Thai adolescents: Implications for health of women and children. J. Med. Toxicol. 8(3), 291-294 (2012). 3. LePage, K.T., Ishmael, J.E., Low, C.M., et al. Differential binding properties of [3H]dextrorphan and [3H] MK-801 in heterologously expressed NMDA receptors. Neuropharmacology 49(1), 1-16 (2005). 4. Kaczor, A.A., Kijkowska-Murak, U.A., and Matosiuk, S. Theoretical studies on the structure and symmetry of the transmembrane region of glutamatergic GluR5 receptor. J. Med. Chem. 51(13), 3765-3776 (2008). 5. Codd, E.E., Shank, R.P., Schupsky, J.J., et al. Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: Structural determinants and role in antinociception. J. Pharmacol. Exp. Ther. 274(3), 1263-1270 (1995).

WARNING CAYMAN CHEMICAL THIS PRODUCT IS FOR RESEARCH ONLY - NOT FOR HUMAN OR VETERINARY DIAGNOSTIC OR THERAPEUTIC USE. 1180 EAST ELLSWORTH RD SAFETY DATA ANN ARBOR, MI 48108 · USA This material should be considered hazardous until further information becomes available. Do not ingest, inhale, get in eyes, on skin, or on clothing. Wash thoroughly after handling. Before use, the user must review the complete Safety Data Sheet, which has been sent via email to your institution. PHONE: [800] 364-9897

WARRANTY AND LIMITATION OF REMEDY [734] 971-3335 Buyer agrees to purchase the material subject to Cayman’s Terms and Conditions. Complete Terms and Conditions including Warranty and Limitation of Liability information can be found on our website. FAX: [734] 971-3640 [email protected] Copyright Cayman Chemical Company, 08/27/2019 WWW.CAYMANCHEM.COM