Synonym
NSC 82357; NSC-82357' NSC82357; Orphenadrine Hydrochloride, BS-5930, BS 5930, BS5930, Disipal, Orphenadrine HCl
IUPAC/Chemical Name
N,N-dimethyl-2-(phenyl(o-tolyl)methoxy)ethan-1-amine hydrochloride
InChi Key
UQZKYYIKWZOKKD-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H23NO.ClH/c1-15-9-7-8-12-17(15)18(20-14-13-19(2)3)16-10-5-4-6-11-16;/h4-12,18H,13-14H2,1-3H3;1H
SMILES Code
CC1=CC=CC=C1C(OCCN(C)C)C2=CC=CC=C2.[H]Cl
Appearance
White to off-white crystalline 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#
83-98-7 (Orphenadrine)
341-69-5 (Orphenadrine Hydrochloride)
Biological target:
Orphenadrine hydrochloride is an orally active and non-competitive NMDA receptor antagonist.
In vitro activity:
Orphenadrine inhibits [3H]MK-801 binding to the phencyclidine (PCP) binding site of the N-methyl-D-aspartate (NMDA)-receptor in homogenates of postmortem human frontal cortex with a Ki-value of 6.0 +/- 0.7 microM. Orphenadrine blocked open NMDA receptor channels with fast kinetics and in a strongly voltage-dependent manner. The IC50-value against steady state currents at -70 mV was 16.2 +/- 1.6 microM (n = 6). Orphenadrine exhibited relatively fast, concentration-dependent open channel blocking kinetics (Kon 0.013 +/- 0.002 10(6) M-1S-1) whereas the offset rate was concentration-independent (Koff 0.230 +/- 0.004 S-1).
Reference: J Neural Transm Gen Sect. 1995;102(3):237-46. https://pubmed.ncbi.nlm.nih.gov/8788072/
In vivo activity:
ORPH (orphenadrine) was administered intraperitoneally (i.p.) in doses of 50-80 mg/kg in male Wistar rats. The latency to first seizure, the number of seizure episodes and the duration of overt status epilepticus (SE) as well as the incidence of deaths was scored with simultaneous electroencephalographic (EEG) recordings. Subsequently, the effects of conventional AEDs on ORPH-evoked (80 mg/kg) seizure incidence were studied. ORPH dose-dependently induced seizures in increasing number of animals, reaching 100% at a dose of 80 mg/kg, associated with low mortality and no drug-related neurotoxicity.
Reference: Brain Res Bull. 2011 Apr 5;84(6):389-93. https://pubmed.ncbi.nlm.nih.gov/21272614/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
33.0 |
107.90 |
| DMSO |
47.0 |
153.67 |
| Ethanol |
10.0 |
32.70 |
| PBS (pH 7.2) |
10.0 |
32.70 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
305.85
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:
1. Pubill D, Verdaguer E, Canudas AM, Sureda FX, Escubedo E, Camarasa J, Pallàs M, Camins A. Orphenadrine prevents 3-nitropropionic acid-induced neurotoxicity in vitro and in vivo. Br J Pharmacol. 2001 Feb;132(3):693-702. doi: 10.1038/sj.bjp.0703869. PMID: 11159722; PMCID: PMC1572610.
2. Kornhuber J, Parsons CG, Hartmann S, Retz W, Kamolz S, Thome J, Riederer P. Orphenadrine is an uncompetitive N-methyl-D-aspartate (NMDA) receptor antagonist: binding and patch clamp studies. J Neural Transm Gen Sect. 1995;102(3):237-46. doi: 10.1007/BF01281158. PMID: 8788072.
3. Chen YW, Tzeng JI, Chen YC, Hung CH, Wang JJ. Intrathecal orphenadrine elicits spinal block in the rat. Eur J Pharmacol. 2014 Nov 5;742:125-30. doi: 10.1016/j.ejphar.2014.08.035. Epub 2014 Sep 6. PMID: 25205132.
4. Rejdak K, Nieoczym D, Czuczwar M, Kiś J, Wlaź P, Turski WA. Orphenadrine induces secondarily generalized convulsive status epilepticus in rats. Brain Res Bull. 2011 Apr 5;84(6):389-93. doi: 10.1016/j.brainresbull.2011.01.014. Epub 2011 Jan 25. PMID: 21272614.
In vitro protocol:
1. Pubill D, Verdaguer E, Canudas AM, Sureda FX, Escubedo E, Camarasa J, Pallàs M, Camins A. Orphenadrine prevents 3-nitropropionic acid-induced neurotoxicity in vitro and in vivo. Br J Pharmacol. 2001 Feb;132(3):693-702. doi: 10.1038/sj.bjp.0703869. PMID: 11159722; PMCID: PMC1572610.
2. Kornhuber J, Parsons CG, Hartmann S, Retz W, Kamolz S, Thome J, Riederer P. Orphenadrine is an uncompetitive N-methyl-D-aspartate (NMDA) receptor antagonist: binding and patch clamp studies. J Neural Transm Gen Sect. 1995;102(3):237-46. doi: 10.1007/BF01281158. PMID: 8788072.
In vivo protocol:
1. Chen YW, Tzeng JI, Chen YC, Hung CH, Wang JJ. Intrathecal orphenadrine elicits spinal block in the rat. Eur J Pharmacol. 2014 Nov 5;742:125-30. doi: 10.1016/j.ejphar.2014.08.035. Epub 2014 Sep 6. PMID: 25205132.
2. Rejdak K, Nieoczym D, Czuczwar M, Kiś J, Wlaź P, Turski WA. Orphenadrine induces secondarily generalized convulsive status epilepticus in rats. Brain Res Bull. 2011 Apr 5;84(6):389-93. doi: 10.1016/j.brainresbull.2011.01.014. Epub 2011 Jan 25. PMID: 21272614.
1: Gokavi NM, Nandibewoor ST, Gowda JI. Investigations of the Interaction Mechanism Between Orphenadrine Hydrochloride and Bovine Serum Albumin by Spectroscopic and Voltammetric Techniques. J Fluoresc. 2023 Sep;33(5):2061-2073. doi: 10.1007/s10895-023-03199-y. Epub 2023 Mar 28. PMID: 36976401.
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6: Ballerini P, Franchi A, Fuschiotti P, Piccioni D, Bonmassar E. Two antiemetic regimens do not impair chemical xenogenization induced in vivo by 5-(3,3-dimethyl-1-triazeno)-imidazole-4-carboxamide. Cancer Chemother Pharmacol. 1989;24(6):359-62. doi: 10.1007/BF00257442. PMID: 2791188.
7: McBride WG, Hicks LJ. Acetylcholine and choline levels in rabbit fetuses exposed to anticholinergics. Int J Dev Neurosci. 1987;5(2):117-25. doi: 10.1016/0736-5748(87)90057-8. PMID: 3503493.
8: Furlanut M, Bettio D, Bertin I, Colombo G, Benetello P. Orphenadrine serum levels in a poisoned patient. Hum Toxicol. 1985 May;4(3):331-3. doi: 10.1177/096032718500400316. PMID: 4007897.
9: Camarda V, Di Carlo A. A controlled study of the effect of orphenadrine hydrochloride (Disipal) on vertigo in patients with spontaneous vestibular disease. Br J Clin Pract. 1982 May;36(5):186-8. PMID: 6756452.
10: Rutigliano G, Labout JJ. The bioavailability of orphenadrine hydrochloride after intramuscular and oral administration. J Int Med Res. 1982;10(6):447-50. doi: 10.1177/030006058201000612. PMID: 7152086.
11: Labout JJ, Thijssen Ct, Keijser GG, Hespe W. Difference between single and multiple dose pharmacokinetics of orphenadrine hydrochloride in man. Eur J Clin Pharmacol. 1982;21(4):343-50. doi: 10.1007/BF00637624. PMID: 7056281.
12: Kelkar MS. Atropine substitutes and the writhing syndrome in mice. Arch Int Pharmacodyn Ther. 1977 Sep;229(1):133-7. PMID: 931459.
13: Attwood D. Aggregation of antiacetylcholine drugs in aqueous solution: micellar properties of some diphenylmethane derivatives. J Pharm Pharmacol. 1976 May;28(5):407-9. doi: 10.1111/j.2042-7158.1976.tb04643.x. PMID: 6747.
14: Capstick N, Pudney H. A comparative trial of orphenadrine and tofenacin in the control of depression and extrapyramidal side-effects associated with fluphenazine decanoate therapy. J Int Med Res. 1976;4(6):435-40. doi: 10.1177/030006057600400610. PMID: 800383.
15: Funcke AB, Timmerman H. Comparison of phenobarbital with orphenadrine hydrochloride and tofenacine hydrochloride for enzyme-inducing activity in young and adult rats. Arch Int Pharmacodyn Ther. 1973 Oct;205(2):213-7. PMID: 4766547.
16: Whyte RK, Hunter KR, Laurence DR, Stern GM, Armitage P. Levodopa and orphenadrine hydrochloride in Parkinsonism. Eur J Clin Pharmacol. 1971 Dec;4(1):18-21. doi: 10.1007/BF00568893. PMID: 4948768.
17: Hespe W, Ernsting MJ, Nauta WT. The effect of orphenadrine hydrochloride on the acetylcholine concentration in rat brain. Int J Neuropharmacol. 1969 Sep;8(5):471-4. doi: 10.1016/0028-3908(69)90063-x. PMID: 5344490.
18: Prins H, Hespe W. Autoradiographic study of the distribution of radioactivity in mice after oral administration of tritium-labelled orphenadrine hydrochloride. Arch Int Pharmacodyn Ther. 1968 Jan;171(1):47-57. PMID: 5646024.
19: DOORENBOS HJ, REKKER RF, VAN DER ROL JH, NAUTA WT. INVESTIGATION OF ORPHENADRINE HYDROCHLORIDE AND ORPHENADRINE CITRATE (BETA- DIMETHYLAMINOETHYL-2-METHYL-BENZHYDRYL ETHER HYDROCHLORIDE AND DIHYDROGEN CITRATE). Pharm Weekbl. 1965 Jul 9;100:841-50. PMID: 14347846.
20: Hespe W, de Roos AM, Nauta WT. Investigation into the metabolic fate of orphenadrine hydrochloride after oral administration to male rats. Arch Int Pharmacodyn Ther. 1965 Jul;156(1):180-200. PMID: 5858833.
