Synonym
Diphemanil Methylsulfate; Prantal; Talpran; metilsulfate; Diphenmethanil; NSC 41725; NSC41725; NSC-41725;
IUPAC/Chemical Name
4-(diphenylmethylene)-1,1-dimethylpiperidin-1-ium methyl sulfate
InChi Key
BREMLQBSKCSNNH-UHFFFAOYSA-M
InChi Code
InChI=1S/C20H24N.CH4O4S/c1-21(2)15-13-19(14-16-21)20(17-9-5-3-6-10-17)18-11-7-4-8-12-18;1-5-6(2,3)4/h3-12H,13-16H2,1-2H3;1H3,(H,2,3,4)/q+1;/p-1
SMILES Code
C[N+]1(C)CC/C(CC1)=C(C2=CC=CC=C2)\C3=CC=CC=C3.O=S(OC)([O-])=O
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, not in water
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
Biological target:
1. Adamantidis M, Dumotier B, Caron J, Dupuis B. Effets électrophysiologiques et potentialité arythmogène du diphémanil méthylsulfate sur les fibres de Purkinje de lapin. Corrélations avec les observations cliniques d'allongement de QT en pédiatrie [Electrophysiologic effects and arrhythmogenic potential of diphemanil methylsulfate on rabbit purkinje fibers. Correlations with clinical observations of QT prolongation in pediatrics]. Arch Mal Coeur Vaiss. 1998 Dec;91(12):1487-94. French. PMID: 9891832.
2. Urios P, Grigorova-Borsos AM, Mozère G, Nakib S, Dauchy F, Peyroux J, Sternberg M. Cyclic guanosylmonophosphate urinary excretion in parasympathicomimetic or parasympatholytic syndromes induced by reserpine or diphemanil-methylsulfate. Life Sci. 1999;64(2):113-23. doi: 10.1016/s0024-3205(98)00541-4. PMID: 10069489.
In vitro activity:
1. Adamantidis M, Dumotier B, Caron J, Dupuis B. Effets électrophysiologiques et potentialité arythmogène du diphémanil méthylsulfate sur les fibres de Purkinje de lapin. Corrélations avec les observations cliniques d'allongement de QT en pédiatrie [Electrophysiologic effects and arrhythmogenic potential of diphemanil methylsulfate on rabbit purkinje fibers. Correlations with clinical observations of QT prolongation in pediatrics]. Arch Mal Coeur Vaiss. 1998 Dec;91(12):1487-94. French. PMID: 9891832.
In vivo activity:
1. Urios P, Grigorova-Borsos AM, Mozère G, Nakib S, Dauchy F, Peyroux J, Sternberg M. Cyclic guanosylmonophosphate urinary excretion in parasympathicomimetic or parasympatholytic syndromes induced by reserpine or diphemanil-methylsulfate. Life Sci. 1999;64(2):113-23. doi: 10.1016/s0024-3205(98)00541-4. PMID: 10069489.
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
10.0 |
25.67 |
| DMSO |
35.7 |
91.72 |
| PBS (pH 7.2) |
10.0 |
25.67 |
| Water |
17.3 |
44.50 |
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
389.51
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 |
1: Biran-Mucignat V, Flamant C, Lachtar M, Perrot C, Chauty A, Novakova J, Lavallée I, Mitanchez D, Aujard Y, Gold F. [Determinants of diphemanil methylsulfate (Prantal) utilization: a survey of practice in the French neonatal and intensive care units]. Arch Pediatr. 2007 Mar;14(3):254-8. Epub 2006 Dec 18. French. PubMed PMID: 17175143.
2: Houri JJ, Gouaillard G, Acar V, Le Hoang MD, Pradeau D, Guyon F. LC determination of diphemanil methylsulfate: application to stability study of stored pharmaceutical formulations. J Pharm Biomed Anal. 2002 Jun 1;28(5):811-8. PubMed PMID: 12039622.
3: Urios P, Grigorova-Borsos AM, Mozère G, Nakib S, Dauchy F, Peyroux J, Sternberg M. Cyclic guanosylmonophosphate urinary excretion in parasympathicomimetic or parasympatholytic syndromes induced by reserpine or diphemanil-methylsulfate. Life Sci. 1999;64(2):113-23. PubMed PMID: 10069489.
4: Chéron G, Vidal AM, Rey E, Pons G, d'Athis P, Olive G. [Pharmacokinetics of diphemanil methylsulfate in infants]. Arch Pediatr. 1994 Jan;1(1):33-7. French. PubMed PMID: 8087216.
5: Laccourreye O, Bonan B, Brasnu D, Laccourreye H. Treatment of Frey's syndrome with topical 2% diphemanil methylsulfate (Prantal): a double-blind evaluation of 15 patients. Laryngoscope. 1990 Jun;100(6):651-3. PubMed PMID: 2190054.
6: Küng M, Diamond L. Effect of inhaled diphemanil methylsulfate, a parasympatholytic agent, on histamine induced bronchoconstriction in asymptomatic asthmatics. Ann Allergy. 1984 Jan;52(1):22-5. PubMed PMID: 6696291.
7: FISHER C. Preliminary report on the use of diphemanil methylsulfate (Prantal) 2 per cent dusting powder in hyperhidrosis and bromhidrosis. J Am Podiatry Assoc. 1963 Aug;53:595-6. PubMed PMID: 13945267.
8: NEW AND nonofficial remedies: diphemanil methylsulfate. J Am Med Assoc. 1955 Jan 22;157(4):342-3. PubMed PMID: 13221425.
9: Adamantidis M, Dumotier B, Caron J, Dupuis B. [Electrophysiologic effects and arrhythmogenic potential of diphemanil methylsulfate on rabbit purkinje fibers. Correlations with clinical observations of QT prolongation in pediatrics]. Arch Mal Coeur Vaiss. 1998 Dec;91(12):1487-94. French. PubMed PMID: 9891832.
10: Cardiac risk with diphemanil methylsulfate in infants. Prescrire Int. 1998 Feb;7(33):21. PubMed PMID: 10183398.
11: Diamond L, O'Donnell M. A comparative study of two parasympatholytic bronchodilator agents: ipratropium bromide and diphemanil methylsulfate. J Pharmacol Exp Ther. 1981 Jan;216(1):1-5. PubMed PMID: 6450282.
12: HACKBARTH DE, MARKSON LS. Diphemanil methylsulfate hyperhidrosis. Arch Dermatol. 1961 Apr;83:659. PubMed PMID: 13710268.
13: HIRSCHMANN VR, URBAN FH. Clinical use of diphemanil methylsulfate as an antiperspirant. U S Armed Forces Med J. 1958 Feb;9(2):177-9. PubMed PMID: 13507243.
14: ORENTREICH N, REIN CR. The effect of diphemanil methylsulfate (prantal) on hyperhidrosis. AMA Arch Derm. 1957 Dec;76(6):762-5. PubMed PMID: 13478170.
15: KOZIE LJ, BALLARD R, BUIVIDAS A. A clinical evaluation of diphemanil methylsulfate in the treatment of hyperhidrosis. J Natl Assoc Chirop. 1957 Aug;47(8):398-400. PubMed PMID: 13449618.
16: WITTICH FW. Diphemanil methylsulfate cream plain and with hydrocortisone in the treatment of various skin diseases. Ann Allergy. 1956 Jan-Feb;14(1):69-75. PubMed PMID: 13292828.
17: JUSTER E. [Effectiveness of an anticholinergic, diphemanil methylsulfate, in therapy of certain dermatoses]. Bull Soc Fr Dermatol Syphiligr. 1955 Mar-Apr;2:157-9. French. PubMed PMID: 13240352.
