Tranylcypromine Sulfate
(C9H11N)2·H2SO4 364.46
Cyclopropanamine, 2-phenyl-, trans-(±)-, sulfate (2:1);
(±)-trans-2-Phenylcyclopropylamine sulfate (2:1)
[13492-01-8].
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(C9H11N)2·H2SO4 364.46
Cyclopropanamine, 2-phenyl-, trans-(±)-, sulfate (2:1);
(±)-trans-2-Phenylcyclopropylamine sulfate (2:1)
[13492-01-8].DEFINITION
Tranylcypromine Sulfate contains NLT 98.0% and NMT 102.0% of (C9H11N)2·H2SO4, calculated on the dried basis.
IDENTIFICATION
• B.
The retention time of the major peak of the Sample solution corresponds to that of the Standard solution, as obtained in the Assay.
• C. Identification Tests—General, Sulfate 
191
:
Meets the requirements
191:
Meets the requirements
ASSAY
• Procedure
Buffer:
Dissolve 3.4 g of monobasic ammonium phosphate in about 900 mL of water in a 1-L volumetric flask. Adjust with phosphoric acid to a pH of 2.2 ± 0.1, and dilute with water to volume.
Mobile phase:
Methanol and Buffer (3:7)
0.05 N sulfuric acid:
Cautiously add 1.3 mL of sulfuric acid to 100 mL of water, cool to room temperature, and dilute to 1000 mL.
Diluent:
Methanol, water, and 0.05 N sulfuric acid (1:3:1)
Standard stock solution:
Using a sonicator, dissolve USP Tranylcypromine Sulfate RS in 0.05 N sulfuric acid and methanol (about 30% of the final volume of each solvent). Dilute with Diluent to obtain a 400 µg/mL solution.
Standard solution:
40 µg/mL of USP Tranylcypromine Sulfate RS in Diluent, prepared from the Standard stock solution
Sample stock solution:
Using a sonicator, dissolve Tranylcypromine Sulfate in methanol and 0.05 N sulfuric acid (about 30% of the final volume of each solvent). Dilute with Diluent to obtain a 400 µg/mL solution.
Sample solution:
40 µg/mL tranylcypromine sulfate in Diluent, prepared from the Sample stock solution
Chromatographic system
Mode:
LC
Detector:
UV 220 nm
Column:
4.6-mm × 25-cm; 4-µm packing L11
Column temperature:
30
Flow rate:
1 mL/min
Injection size:
20 µL
System suitability
Sample:
Standard solution
Suitability requirements
Tailing factor:
NMT 2.0
Relative standard deviation:
NMT 2.0%
Analysis
Samples:
Standard solution and Sample solution
Calculate the percentage of (C9H11N)2·H2SO4 in the portion taken:
Result = (rU/rS) × (CS/CU) × 100
| rU | = | = peak response from the Sample solution |
| rS | = | = peak response from the Standard solution |
| CS | = | = concentration of USP Tranylcypromine Sulfate RS in the Standard solution (µg/mL) |
| CU | = | = concentration of tranylcypromine sulfate in the Sample solution (µg/mL) |
Acceptance criteria:
98.0%–102.0% on the dried basis
IMPURITIES
Organic Impurities
• Procedure
Buffer, 0.05 N sulfuric acid, and Diluent:
Proceed as directed in the Assay.
Solution A:
Methanol and Buffer (3:17)
Solution B:
Methanol and Buffer (3:7)
Mobile phase:
See the gradient table below.
| Time (min) |
Solution A (%) |
Solution B (%) |
|---|---|---|
| 0 | 100 | 0 |
| 20 | 100 | 0 |
| 25 | 0 | 100 |
| 37 | 0 | 100 |
| 39 | 100 | 0 |
| 45 | 100 | 0 |
Standard stock solution:
14 µg/mL of USP Tranylcypromine Sulfate RS, and 60 µg/mL each of USP Tranylcypromine Related Compound A RS and USP Tranylcypromine Related Compound B RS in Diluent. [Note—Sonicate as needed. ]
Standard solution:
Transfer a portion of the Standard stock solution to a suitable volumetric flask containing methanol and 0.05 N sulfuric acid (30% of the final volume of each solvent). Dilute with Diluent to volume to obtain a solution containing 0.7 µg/mL of USP Tranylcypromine Sulfate RS and 3.0 µg/mL each of USP Tranylcypromine Related Compound A RS and USP Tranylcypromine Related Compound B RS.
Sample solution:
Using a sonicator, dissolve Tranylcypromine Sulfate in methanol and 0.05 N sulfuric acid (about 30% of the final volume of each solvent). Dilute with Diluent to obtain a solution containing 680 µg/mL of tranylcypromine sulfate.
Chromatographic system
Mode:
LC
Detector:
UV 249 nm for tranylcypromine related compound B; 220 nm for all other specified and unspecified impurities
Column:
4.6-mm × 15-cm; 3-µm packing L1
Column temperature:
35
Flow rate:
1.2 mL/min
Injection size:
25 µL
System suitability
Sample:
Standard solution
Suitability requirements
Resolution:
NLT 2.0 between tranylcypromine and tranylcypromine related compound A, determined at 220 nm
Tailing factor:
NMT 2.0 for tranylcypromine, determined at 220 nm
Relative standard deviation:
NMT 6.0% for tranylcypromine and tranylcypromine related compound A, determined at 220 nm; NMT 6.0% for tranylcypromine related compound B, determined at 249 nm.
Analysis
Samples:
Standard solution and Sample solution
[Note—Disregard the signal for tranylcypromine related compound B observed at 220 nm. ]
Identify tranylcypromine related compound A, cis-hydrazide, trans-hydrazide, and any unspecified impurity using the data in Impurity Table 1. Calculate the percentage of each impurity in the portion of sample taken:
Result = (rU/rS) × (CS/CU) × 100/F
| rU | = | = peak response of the impurity from the Sample solution |
| rS | = | = peak response of the Standard solution |
| CS | = | = concentration of USP Tranylcypromine Sulfate RS in the Standard solution (µg/mL) |
| CU | = | = concentration of Tranylcypromine Sulfate in the Sample solution (µg/mL) |
| F | = | = response factor relative to tranylcypromine sulfate |
Calculate the percentage of tranylcypromine related compound B in the portion of sample taken:
Result = (rU/rS) × (CS/CU) × (Mr1/Mr2) × 100
| rU | = | = peak response at 249 nm of tranylcypromine related compound B from the Sample solution |
| rS | = | = peak response at 249 nm of tranylcypromine related compound B from the Standard solution |
| CS | = | = concentration of USP Tranylcypromine Related Compound B RS in the Standard solution (µg/mL) |
| CU | = | = concentration of Tranylcypromine Sulfate in the Sample solution (µg/mL) |
| Mr1 | = | = molecular weight of 3-phenylallylamine free base, 133.19 |
| Mr2 | = | = molecular weight of 3-phenylallylamine hydrochloride (USP Tranylcypromine Related Compound B RS), 169.66 |
Acceptance criteria
Individual impurities:
See Impurity Table 1. [Note—Tranylcypromine related compound B is determined at 249 nm. All other specified and unspecified impurities are determined at 220 nm. ]
Total impurities:
NMT 1.0% for sum of tranylcypromine related compound A, tranylcypromine related compound B, cis-hydrazide, trans-hydrazide, and any unspecified impurity.
Impurity Table 1
| Name | Relative Retention Time |
Relative Response Factor |
Acceptance Criteria, NMT (%) |
|---|---|---|---|
| Tranylcypromine related compound Aa | 0.82 | 0.74 | 0.50 |
| Tranylcypromine sulfate | 1.0 | 1.0 | — |
| Tranylcypromine related compound Bb | 1.2 | — | 0.50 |
| cis-Hydrazidec | 1.4 | 0.86 | 0.50 |
| trans-Hydrazided | 2.5 | 1.1 | 0.50 |
| Any unspecified impurity | — | 1.0 | 0.10 |
|
a
(±)-cis-2-Phenylcyclopropanamine (cis-Cypromine).
b
3-Phenylallylamine (Cinnamylamine), monitored at 249 nm.
c
(±)-cis-2-Phenylcyclopropanecarbohydrazide.
d
(±)-trans-2-Phenylcyclopropanecarbohydrazide.
|
|||
SPECIFIC TESTS
• Loss on Drying 731:
Dry a sample in vacuum at 60 for 2 h: it loses NMT 0.5% of its weight.
731:
Dry a sample in vacuum at 60 for 2 h: it loses NMT 0.5% of its weight.
ADDITIONAL REQUIREMENTS
• Packaging and Storage:
Preserve in well-closed containers.
• USP Reference Standards 11
11
USP Tranylcypromine Sulfate RS 
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USP Tranylcypromine Related Compound A RS
(±)-cis-2-Phenylcyclopropanamine hydrochloride; cis-tranylcypromine hydrochloride.
C9H11N·HCl 169.65
(±)-cis-2-Phenylcyclopropanamine hydrochloride; cis-tranylcypromine hydrochloride.
C9H11N·HCl 169.65
USP Tranylcypromine Related Compound B RS
3-Phenylallylamine hydrochloride; cinnamylamine hydrochloride.
C9H11N·HCl 169.65
3-Phenylallylamine hydrochloride; cinnamylamine hydrochloride.
C9H11N·HCl 169.65
Auxiliary Information—
Please check for your question in the FAQs before contacting USP.
| Topic/Question | Contact | Expert Committee |
|---|---|---|
| Monograph | Hariram Ramanathan, M.S.
Associate Scientific Liaison 1-301-816-8313 |
(SM42010) Monographs - Small Molecules 4 |
| Reference Standards | RS Technical Services 1-301-816-8129 rstech@usp.org |
USP35–NF30 Page 4912
Pharmacopeial Forum: Volume No. 35(2) Page 314