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MedKoo Cat#: 413755 | Name: Dimemorfan phosphate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dimemorfan phosphate is an antitussive of the morphinan family that is widely used in Japan and is also marketed in Spain and Italy. It was developed by Yamanouchi Pharmaceutical and introduced in Japan in 1975.

Chemical Structure

Dimemorfan phosphate
CAS#36304-84-4 (phosphate)

Theoretical Analysis

MedKoo Cat#: 413755

Name: Dimemorfan phosphate

CAS#: 36304-84-4 (phosphate)

Chemical Formula: C18H28NO4P

Exact Mass: 0.0000

Molecular Weight: 353.39

Elemental Analysis: C, 61.18; H, 7.99; N, 3.96; O, 18.11; P, 8.76

Price and Availability

Size Price Availability Quantity
50mg USD 250.00 2 Weeks
100mg USD 450.00 2 Weeks
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Related CAS #
36304-84-4 (phosphate) 36304-82-2 (free base)
Synonym
Dimemorfan phosphate; Astomin; Gentus; Dimemorfan (phosphate); AT17; AT-17; AT 17;
IUPAC/Chemical Name
(4bS,8aS,9S)-3,11-dimethyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene phosphate
InChi Key
ODJHDWLIOUGPPA-URVXVIKDSA-N
InChi Code
InChI=1S/C18H25N.H3O4P/c1-13-6-7-14-12-17-15-5-3-4-8-18(15,16(14)11-13)9-10-19(17)2;1-5(2,3)4/h6-7,11,15,17H,3-5,8-10,12H2,1-2H3;(H3,1,2,3,4)/t15-,17+,18+;/m1./s1
SMILES Code
CC1=CC2=C(C[C@H]3[C@@H]4[C@]2(CCCC4)CCN3C)C=C1.OP(=O)(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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 353.39 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.

Recalculate based on batch purity %
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
1: Shen Y, Luo Z, Yu Q, Wang Y, Xiang J, Miao J. Pharmacokinetics of dimemorfan phosphate tablets in healthy Chinese volunteers. Eur J Clin Pharmacol. 2017 Jun;73(6):709-715. doi: 10.1007/s00228-017-2211-9. Epub 2017 Feb 28. PMID: 28243685. 2: Wei X, Zheng Z, Feng Z, Zheng L, Tao S, Zheng B, Huang B, Zhang X, Liu J, Chen Y, Zong W, Shan Z, Fan S, Chen J, Zhao F. Sigma-1 receptor attenuates osteoclastogenesis by promoting ER-associated degradation of SERCA2. EMBO Mol Med. 2022 Jul 7;14(7):e15373. doi: 10.15252/emmm.202115373. Epub 2022 May 25. PMID: 35611810; PMCID: PMC9260208. 3: Ida H. The nonnarcotic antitussive drug dimemorfan: a review. Clin Ther. 1997 Mar-Apr;19(2):215-31. doi: 10.1016/s0149-2918(97)80111-7. PMID: 9152562. 4: Chou YC, Ueng YF, Chou CY, Tien JH. Dimemorfan N-demethylation by mouse liver microsomal cytochrome P450 enzymes. Life Sci. 2005 Jul 1;77(7):735-45. doi: 10.1016/j.lfs.2004.11.037. PMID: 15936348. 5: Wang YH, Shen YC, Liao JF, Lee CH, Chou CY, Liou KT, Chou YC. Anti- inflammatory effects of dimemorfan on inflammatory cells and LPS-induced endotoxin shock in mice. Br J Pharmacol. 2008 Jul;154(6):1327-38. doi: 10.1038/bjp.2008.202. Epub 2008 May 26. Erratum in: Br J Pharmacol. 2008 Aug;154(8):1702. Li, C-H [corrected to Lee, C-H]. PMID: 18500357; PMCID: PMC2483385. 6: Shin EJ, Nabeshima T, Lee PH, Kim WK, Ko KH, Jhoo JH, Jhoo WK, Cha JY, Kim HC. Dimemorfan prevents seizures induced by the L-type calcium channel activator BAY k-8644 in mice. Behav Brain Res. 2004 May 5;151(1-2):267-76. doi: 10.1016/j.bbr.2003.09.004. PMID: 15084442. 7: Shen YC, Wang YH, Chou YC, Liou KT, Yen JC, Wang WY, Liao JF. Dimemorfan protects rats against ischemic stroke through activation of sigma-1 receptor- mediated mechanisms by decreasing glutamate accumulation. J Neurochem. 2008 Jan;104(2):558-72. doi: 10.1111/j.1471-4159.2007.05058.x. PMID: 18173806. 8: Tan H, Peng J, Pei Q, Yang L, Chen J, Guo C, Hua Y, Yuan H, Yang G. Simple and sensitive LC-MS/MS-based assay for the quantification of dimemorfan in human plasma for use in a pharmacokinetic study. Biomed Chromatogr. 2015 May;29(5):647-53. doi: 10.1002/bmc.3325. Epub 2014 Sep 29. PMID: 25262813. 9: Wang HH, Chien JW, Chou YC, Liao JF, Chen CF. Anti-amnesic effect of dimemorfan in mice. Br J Pharmacol. 2003 Mar;138(5):941-9. doi: 10.1038/sj.bjp.0705117. PMID: 12642396; PMCID: PMC1573728. 10: Pei Q, Peng J, Tan H, Yang L, Yang X, Liu L, Liu S, Yuan H, Yang G. Cytochrome P450 2D6*10 genotype affects the pharmacokinetics of dimemorfan in healthy Chinese subjects. Eur J Drug Metab Pharmacokinet. 2015 Dec;40(4):427-33. doi: 10.1007/s13318-014-0221-x. Epub 2014 Aug 27. PMID: 25159483. 11: Shin EJ, Nah SY, Kim WK, Ko KH, Jhoo WK, Lim YK, Cha JY, Chen CF, Kim HC. The dextromethorphan analog dimemorfan attenuates kainate-induced seizures via sigma1 receptor activation: comparison with the effects of dextromethorphan. Br J Pharmacol. 2005 Apr;144(7):908-18. doi: 10.1038/sj.bjp.0705998. PMID: 15723099; PMCID: PMC1576070. 12: Chou YC, Liao JF, Chang WY, Lin MF, Chen CF. Binding of dimemorfan to sigma-1 receptor and its anticonvulsant and locomotor effects in mice, compared with dextromethorphan and dextrorphan. Brain Res. 1999 Mar 13;821(2):516-9. doi: 10.1016/s0006-8993(99)01125-7. PMID: 10064839. 13: Kigoshi S, Kitajima K, Nishio M. Effect of dextromethorphan and dimemorfan on the neutral lipids of tumor cells. Jpn J Pharmacol. 1984 Feb;34(2):258-60. doi: 10.1254/jjp.34.258. PMID: 6748373. 14: Hasegawa C, Kumazawa T, Terada M, Lee XP, Sato K, Uchigasaki S, Kurosaki K. A new method for quantitative determination of dimemorfan in human plasma using monolithic silica solid-phase extraction tips. Leg Med (Tokyo). 2012 Sep;14(5):267-71. doi: 10.1016/j.legalmed.2012.03.004. Epub 2012 Apr 28. PMID: 22546247. 15: Wang SJ, Xiang J, Yu Q, Liang MZ, Nan F, Qin YP. [Determination of dimemorfan in human plasma and urine with HPLC-MS/MS]. Sichuan Da Xue Xue Bao Yi Xue Ban. 2014 May;45(3):497-501. Chinese. PMID: 24941827. 16: Kim JY, Kim HC, Kim J, Lee J. Concise synthesis of dimemorfan (DF) starting from 3-hydroxymorphinan (3-HM). Chem Pharm Bull (Tokyo). 2008 Jul;56(7):985-7. doi: 10.1248/cpb.56.985. PMID: 18591815. 17: Chou YC, Chung YT, Liu TY, Wang SY, Chau GY, Chi CW, Soucek P, Krausz KW, Gelboin HV, Lee CH, Ueng YF. The oxidative metabolism of dimemorfan by human cytochrome P450 enzymes. J Pharm Sci. 2010 Feb;99(2):1063-77. doi: 10.1002/jps.21866. PMID: 19593786. 18: Kigoshi S, Nishio M, Kokubo M. Effect of the centrally acting antitussives on ascites tumor cells. Jpn J Pharmacol. 1983 Apr;33(2):343-8. doi: 10.1254/jjp.33.343. PMID: 6887645. 19: Kataoka H, Ura K, Saita T. [Development of a Simple and Sensitive Enzyme- linked Immunosorbent Assay for Sinomenine]. Yakugaku Zasshi. 2023;143(2):153-158. Japanese. doi: 10.1248/yakushi.22-00164. PMID: 36724928. 20: Shin EJ, Bach JH, Lee SY, Kim JM, Lee J, Hong JS, Nabeshima T, Kim HC. Neuropsychotoxic and neuroprotective potentials of dextromethorphan and its analogs. J Pharmacol Sci. 2011;116(2):137-48. doi: 10.1254/jphs.11r02cr. Epub 2011 May 21. PMID: 21606622.