WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H328072
CAS#: 143-98-6 (tartrate)
Description: Dextrophan tartrate is a glutamate receptor antagonist potentially for the treatment of stroke. Dextrorphan (DXO) is a psychoactive drug of the morphinan chemical class which acts as an antitussive or cough suppressant and dissociative hallucinogen. It is the dextrorotatory-stereoisomer of racemorphan, the levo-half being levorphanol. Dextrorphan is produced by O-demethylation of dextromethorphan by CYP2D6. Dextrorphan is an NMDA antagonist and contributes to the psychoactive effects of dextromethorphan. This product is unscheduled in the USA.
Hodoodo Cat#: H328072
Name: Dextrorphan tartrate
CAS#: 143-98-6 (tartrate)
Chemical Formula: C21H29NO7
Exact Mass: 0.00
Molecular Weight: 407.463
Elemental Analysis: C, 61.90; H, 7.17; N, 3.44; O, 27.49
Related CAS #: 69376-27-8 (HCl) 125-73-5 (free base) 143-98-6 (tartrate)
Synonym: Dextrorphan tartrate; Ro 1-6794; Ro-1-6794; Ro1-6794.
IUPAC/Chemical Name: (4bS,8aS,9S)-11-methyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthren-3-ol (2R,3R)-2,3-dihydroxysuccinate
InChi Key: RWTWIZDKEIWLKQ-XCPWPWHNSA-N
InChi Code: InChI=1S/C17H23NO.C4H6O6/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17;5-1(3(7)8)2(6)4(9)10/h5-6,11,14,16,19H,2-4,7-10H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t14-,16+,17+;1-,2-/m11/s1
SMILES Code: OC1=CC=C2C[C@@]3([H])[C@@]4([H])CCCC[C@@]4(CCN3C)C2=C1.O=C(O)[C@H](O)[C@@H](O)C(O)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info: Related CAS# Dextrorphan free base [INN:BAN]: 125-73-5 Dextrophan tartrate: 143-98-6 Dextrorphan sulfate: 19153-86-7 Dextrorphan hydrochloride [USAN]: 69376-27-8 Dextrorphan citrate: 130940-64-6
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 407.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Yamamoto A, Kurogi K, Schiefer IT, Liu MY, Sakakibara Y, Suiko M, Liu MC. Human Cytosolic Sulfotransferase SULT1A3 Mediates the Sulfation of Dextrorphan. Biol Pharm Bull. 2016;39(9):1432-6. doi: 10.1248/bpb.b16-00015. PubMed PMID: 27582324.
2: Unger KA, Watterson JH. Analysis of Dextromethorphan and Dextrorphan in Skeletal Remains Following Decomposition in Different Microclimate Conditions. J Anal Toxicol. 2016 Oct;40(8):669-676. PubMed PMID: 27562970.
3: Fraser CD, Cornthwaite HM, Watterson JH. Analysis of dextromethorphan and dextrorphan in decomposed skeletal tissues by microwave assisted extraction, microplate solid-phase extraction and gas chromatography- mass spectrometry (MAE-MPSPE-GCMS). Drug Test Anal. 2015 Aug;7(8):708-13. doi: 10.1002/dta.1754. PubMed PMID: 25487525.
4: Ding Y, Huang K, Chen L, Yang J, Xu WY, Xu XJ, Duan R, Zhang J, He Q. Simultaneous quantitative analysis of dextromethorphan, dextrorphan and chlorphenamine in human plasma by liquid chromatography-electrospray tandem mass spectrometry. Biomed Chromatogr. 2014 Mar;28(3):446-52. doi: 10.1002/bmc.3054. PubMed PMID: 24254834.
5: Donato JL, Koizumi F, Pereira AS, Mendes GD, De Nucci G. Simultaneous determination of dextromethorphan, dextrorphan and doxylamine in human plasma by HPLC coupled to electrospray ionization tandem mass spectrometry: application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jun 15;899:46-56. doi: 10.1016/j.jchromb.2012.05.001. PubMed PMID: 22651995.
6: Trojan A, Vergopoulos A, Breitenstein U, Seifert B, Rageth C, Joechle W. The Discriminatory Value of CYP2D6 Genotyping in Predicting the Dextromethorphan/Dextrorphan Phenotype in Women with Breast Cancer. Breast Care (Basel). 2012 Feb;7(1):25-31. PubMed PMID: 22553469; PubMed Central PMCID: PMC3335358.
7: Jurica J, Bartecek R, Zourkova A, Pindurova E, Sulcova A, Kasparek T, Zendulka O. Serum dextromethorphan/dextrorphan metabolic ratio for CYP2D6 phenotyping in clinical practice. J Clin Pharm Ther. 2012 Aug;37(4):486-90. doi: 10.1111/j.1365-2710.2012.01333.x. PubMed PMID: 22548589.
8: Lauterbach EC. An extension of hypotheses regarding rapid-acting, treatment-refractory, and conventional antidepressant activity of dextromethorphan and dextrorphan. Med Hypotheses. 2012 Jun;78(6):693-702. doi: 10.1016/j.mehy.2012.02.012. PubMed PMID: 22401777.
9: Liu YJ, Wu HL, Nie JF, Wang JY, Ouyang LQ, Yu RQ. Simultaneous determination of dextromethorphan and its metabolite dextrorphan in plasma samples using second-order calibration coupled with excitation-emission matrix fluorescence. Anal Sci. 2011;27(6):663-6. PubMed PMID: 21666367.
10: Chen YW, Chu CC, Chen YC, Hung CH, Hsueh MI, Wang JJ. Clonidine as adjuvant for oxybuprocaine, bupivacaine or dextrorphan has a significant peripheral action in intensifying and prolonging analgesia in response to local dorsal cutaneous noxious pinprick in rats. Neurosci Lett. 2011 Jun 8;496(3):186-90. doi: 10.1016/j.neulet.2011.04.021. PubMed PMID: 21524685.
11: Miller SC. Dextromethorphan to dextrorphan: a pathway towards abuse liability. Hum Psychopharmacol. 2011 Jan;26(1):89-90; author reply 91. doi: 10.1002/hup.1164. PubMed PMID: 23055419.
12: Chen YW, Wang JJ, Liu TY, Chen YC, Hung CH. Systemic dextromethorphan and dextrorphan are less toxic in rats than bupivacaine at equianesthetic doses. Can J Anaesth. 2011 Jan;58(1):55-61. doi: 10.1007/s12630-010-9408-z. PubMed PMID: 21042903.
13: Loos WJ, de Graan AJ, de Bruijn P, van Schaik RH, van Fessem MA, Lam MH, Mathijssen RH, Wiemer EA. Simultaneous quantification of dextromethorphan and its metabolites dextrorphan, 3-methoxymorphinan and 3-hydroxymorphinan in human plasma by ultra performance liquid chromatography/tandem triple-quadrupole mass spectrometry. J Pharm Biomed Anal. 2011 Jan 25;54(2):387-94. doi: 10.1016/j.jpba.2010.08.033. PubMed PMID: 20926215.
14: Spanakis M, Vizirianakis IS, Mironidou-Tzouveleki M, Niopas I. A validated SIM GC/MS method for the simultaneous determination of dextromethorphan and its metabolites dextrorphan, 3-methoxymorphinan and 3-hydroxymorphinan in biological matrices and its application to in vitro CYP2D6 and CYP3A4 inhibition study. Biomed Chromatogr. 2009 Nov;23(11):1131-7. doi: 10.1002/bmc.1234. PubMed PMID: 19444798.
15: Liang X, Li Y, Barfield M, Ji QC. Study of dried blood spots technique for the determination of dextromethorphan and its metabolite dextrorphan in human whole blood by LC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Mar 15;877(8-9):799-806. doi: 10.1016/j.jchromb.2009.02.015. PubMed PMID: 19237324.
16: Kamel IR, Wendling WW, Chen D, Wendling KS, Harakal C, Carlsson C. N-methyl-D-aspartate (NMDA) antagonists--S(+)-ketamine, dextrorphan, and dextromethorphan--act as calcium antagonists on bovine cerebral arteries. J Neurosurg Anesthesiol. 2008 Oct;20(4):241-8. doi: 10.1097/ANA.0b013e31817f523f. PubMed PMID: 18812887.
17: Van LM, Sarda S, Hargreaves JA, Rostami-Hodjegan A. Metabolism of dextrorphan by CYP2D6 in different recombinantly expressed systems and its implications for the in vitro assessment of dextromethorphan metabolism. J Pharm Sci. 2009 Feb;98(2):763-71. doi: 10.1002/jps.21455. PubMed PMID: 18543297.
18: Rodrigues WC, Wang G, Moore C, Agrawal A, Vincent MJ, Soares JR. Development and validation of ELISA and GC-MS procedures for the quantification of dextromethorphan and its main metabolite dextrorphan in urine and oral fluid. J Anal Toxicol. 2008 Apr;32(3):220-6. PubMed PMID: 18397573.
19: Chen YW, Liu KS, Wang JJ, Chou W, Hung CH. Isobolographic analysis of epinephrine with bupivacaine, dextromethorphan, 3-methoxymorphinan, or dextrorphan on infiltrative anesthesia in rats: dose-response studies. Reg Anesth Pain Med. 2008 Mar-Apr;33(2):115-21. doi: 10.1016/j.rapm.2007.08.012. PubMed PMID: 18299091.
20: Kanaan M, Daali Y, Dayer P, Desmeules J. Lack of interaction of the NMDA receptor antagonists dextromethorphan and dextrorphan with P-glycoprotein. Curr Drug Metab. 2008 Feb;9(2):144-51. PubMed PMID: 18288956.
