WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H318896
CAS#: 13492-01-8 (sulfate)
Description: Tranylcypromine is a monoamine oxidase inhibitor (MAOI)—it is a nonselective and irreversible inhibitor of the enzyme monoamine oxidase (MAO). It is used as an antidepressant and anxiolytic agent in the clinical treatment of mood and anxiety disorders, respectively.
Hodoodo Cat#: H318896
Name: Tranylcypromine sulfate
CAS#: 13492-01-8 (sulfate)
Chemical Formula: C18H24N2O4S
Exact Mass: 133.09
Molecular Weight: 364.460
Elemental Analysis: C, 59.32; H, 6.64; N, 7.69; O, 17.56; S, 8.80
Related CAS #: 13492-01-8 (sulfate) 155-09-9 (free base) 54779-58-7 (Cis_HCl) 4548-34-9 (HCl)
Synonym: Tranylcypromine, Parnate, d-Tranylcypromine, Transamine; SKF 385; SKF-385; SKF385; SKF Trans-385; NSC 80664;
IUPAC/Chemical Name: (1R,2S)-2-phenylcyclopropan-1-amine; sulfuric acid (2:1)
InChi Key: BKPRVQDIOGQWTG-FKXFVUDVSA-N
InChi Code: InChI=1S/2C9H11N.H2O4S/c2*10-9-6-8(9)7-4-2-1-3-5-7;1-5(2,3)4/h2*1-5,8-9H,6,10H2;(H2,1,2,3,4)/t2*8-,9+;/m00./s1
SMILES Code: N[C@H]1[C@H](C2=CC=CC=C2)C1.N[C@H]3[C@H](C4=CC=CC=C4)C3.O=S(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: 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
More Info:
| Biological target: | Tranylcypromine sulfate is a monoamine oxidase (MAO) inhibitor. |
| In vitro activity: | The effects of tranylcypromine on LPS-induced proinflammatory cytokine responses were assessed by pretreating BV2 microglial cells with LPS (200 ng/mL) or PBS for 30 min before treatment with tranylcypromine (1 or 5 μM) or vehicle (1% DMSO) for 5.5 h. Post treatment with 1 μM tranylcypromine did not alter any proinflammatory cytokine levels (Figure S1A–E). However, when the post treatment concentration of tranylcypromine was increased to 5 μM, significant decreases in LPS-mediated proinflammatory cytokine IL-1β and IL-6 mRNA levels were observed (Figure S1A–E). In parallel experiments, BV2 microglial cells were pretreated with tranylcypromine (1 or 5 μM) or vehicle (1% DMSO) for 30 min before treatment with LPS (200 ng/mL) or PBS for 5.5 h. Pretreatment with 5 μM tranylcypromine reduced the level of IL-1β, but not the levels of other proinflammatory cytokines induced by 200 ng/mL LPS (Figure S1F–J). Reference: Cells. 2020 Aug 28;9(9):1982. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7563969/ |
| In vivo activity: | It was examined whether tranylcypromine regulates LPS-induced microglial and astrocyte activation in vivo. Wild-type mice were injected with tranylcypromine (3 mg/kg, i.p.) or PBS daily for 3 days and subsequently injected with LPS (10 mg/kg, i.p.) or PBS. Tranylcypromine significantly downregulated LPS-stimulated microglial activation in the cortex and hippocampus (Figure 4A–H). However, tranylcypromine significantly downregulated LPS-induced astrocyte activation only in the cortex (Figure 4I–P), suggesting that the effects of tranylcypromine on LPS-mediated microgliosis are greater than those on astrogliosis in wild-type mice. These data indicate that tranylcypromine modulates LPS-induced microglial activation in wild-type mice. Reference: Cells. 2020 Aug 28;9(9):1982. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7563969/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| Water | 25.0 | 68.59 | |
| DMSO | 3.5 | 9.60 |
The following data is based on the product molecular weight 364.46 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: | 1. Park H, Han KM, Jeon H, Lee JS, Lee H, Jeon SG, Park JH, Kim YG, Lin Y, Lee YH, Jeong YH, Hoe HS. The MAO Inhibitor Tranylcypromine Alters LPS- and Aβ-Mediated Neuroinflammatory Responses in Wild-type Mice and a Mouse Model of AD. Cells. 2020 Aug 28;9(9):1982. doi: 10.3390/cells9091982. PMID: 32872335; PMCID: PMC7563969. |
| In vitro protocol: | 1. Park H, Han KM, Jeon H, Lee JS, Lee H, Jeon SG, Park JH, Kim YG, Lin Y, Lee YH, Jeong YH, Hoe HS. The MAO Inhibitor Tranylcypromine Alters LPS- and Aβ-Mediated Neuroinflammatory Responses in Wild-type Mice and a Mouse Model of AD. Cells. 2020 Aug 28;9(9):1982. doi: 10.3390/cells9091982. PMID: 32872335; PMCID: PMC7563969. |
| In vivo protocol: | 1. Park H, Han KM, Jeon H, Lee JS, Lee H, Jeon SG, Park JH, Kim YG, Lin Y, Lee YH, Jeong YH, Hoe HS. The MAO Inhibitor Tranylcypromine Alters LPS- and Aβ-Mediated Neuroinflammatory Responses in Wild-type Mice and a Mouse Model of AD. Cells. 2020 Aug 28;9(9):1982. doi: 10.3390/cells9091982. PMID: 32872335; PMCID: PMC7563969. |
1: Gahr M, Schönfeldt-Lecuona C, Kölle MA, Freudenmann RW. Intoxications with the monoamine oxidase inhibitor tranylcypromine: an analysis of fatal and non-fatal events. Eur Neuropsychopharmacol. 2013 Nov;23(11):1364-72. doi: 10.1016/j.euroneuro.2013.05.009. Epub 2013 Jun 19. Review. PubMed PMID: 23791433.
2: Krings-Ernst I, Ulrich S, Adli M. Antidepressant treatment with MAO-inhibitors during general and regional anesthesia: a review and case report of spinal anesthesia for lower extremity surgery without discontinuation of tranylcypromine. Int J Clin Pharmacol Ther. 2013 Oct;51(10):763-70. doi: 10.5414/CP201898. Review. PubMed PMID: 23993253.
3: Gahr M, Schönfeldt-Lecuona C, Kölle MA, Freudenmann RW. Withdrawal and discontinuation phenomena associated with tranylcypromine: a systematic review. Pharmacopsychiatry. 2013 Jun;46(4):123-9. doi: 10.1055/s-0032-1333265. Epub 2013 Jan 28. Review. PubMed PMID: 23359339.
4: Iwersen S, Schmoldt A. One fatal and one nonfatal intoxication with tranylcypromine. Absence of amphetamines as metabolites. J Anal Toxicol. 1996 Sep;20(5):301-4. Review. PubMed PMID: 8872238.
5: Baker GB, Coutts RT, McKenna KF, Sherry-McKenna RL. Insights into the mechanisms of action of the MAO inhibitors phenelzine and tranylcypromine: a review. J Psychiatry Neurosci. 1992 Nov;17(5):206-14. Review. PubMed PMID: 1362653; PubMed Central PMCID: PMC1188458.
6: Frieling H, Bleich S. Tranylcypromine: new perspectives on an "old" drug. Eur Arch Psychiatry Clin Neurosci. 2006 Aug;256(5):268-73. Review. PubMed PMID: 16927039.
7: Briggs NC, Jefferson JW, Koenecke FH. Tranylcypromine addiction: a case report and review. J Clin Psychiatry. 1990 Oct;51(10):426-9. Review. PubMed PMID: 2211541.
8: Atkinson RM, Ditman KS. Tranylcypromine: a review. Clin Pharmacol Ther. 1965 Sep-Oct;6(5):631-55. Review. PubMed PMID: 5320592.
