S-Methylthiocitrulline | CAS#156719-41-4 | nitric oxide synthase inhibitor

MedKoo Cat#: 597698 | Name: S-Methylthiocitrulline

Description:

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

S-Methylthiocitrulline is a nitric oxide synthase inhibitor.

Chemical Structure

S-Methylthiocitrulline

CAS#156719-41-4

Theoretical Analysis

MedKoo Cat#: 597698

Name: S-Methylthiocitrulline

CAS#: 156719-41-4

Chemical Formula: C7H15N3O2S

Exact Mass: 205.0885

Molecular Weight: 205.27

Elemental Analysis: C, 40.96; H, 7.37; N, 20.47; O, 15.59; S, 15.62

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

S-Methylthiocitrulline; S-Me-TC; S-Methyl-L-thiocitrulline;

IUPAC/Chemical Name

(S)-2-amino-5-((imino(methylthio)methyl)amino)pentanoic acid

InChi Key

NGVMVBQRKZPFLB-YFKPBYRVSA-N

InChi Code

InChI=1S/C7H15N3O2S/c1-13-7(9)10-4-2-3-5(8)6(11)12/h5H,2-4,8H2,1H3,(H2,9,10)(H,11,12)/t5-/m0/s1

SMILES Code

N[C@@H](CCCNC(SC)=N)C(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

Shelf Life

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 205.27 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: Matthews RT, Yang L, Beal MF. S-Methylthiocitrulline, a neuronal nitric oxide synthase inhibitor, protects against malonate and MPTP neurotoxicity. Exp Neurol. 1997 Feb;143(2):282-6. PubMed PMID: 9056390. 2: Ago Y, Kawasaki T, Nashida T, Ota Y, Cong Y, Kitamoto M, Takahashi T, Takuma K, Matsuda T. SEA0400, a specific Na+/Ca2+ exchange inhibitor, prevents dopaminergic neurotoxicity in an MPTP mouse model of Parkinson's disease. Neuropharmacology. 2011 Dec;61(8):1441-51. doi: 10.1016/j.neuropharm.2011.08.041. Epub 2011 Sep 2. PubMed PMID: 21903118. 3: Rocha JN. Effect of S-methyl-l-thiocitrulline dihydrochloride on rat micturition reflex. Int Braz J Urol. 2016 Sep-Oct;42(5):1018-1027. doi: 10.1590/S1677-5538.IBJU.2015.0153. PubMed PMID: 24893916; PubMed Central PMCID: PMC5066901. 4: Lu A, Wagner KR, Broderick JP, Clark JF. Administration of S-methyl-L-thiocitrulline protects against brain injuries after intracerebral hemorrhage. Neuroscience. 2014 Jun 13;270:40-7. doi: 10.1016/j.neuroscience.2014.04.004. Epub 2014 Apr 13. PubMed PMID: 24726981; PubMed Central PMCID: PMC4042410. 5: Idigo WO, Reilly S, Zhang MH, Zhang YH, Jayaram R, Carnicer R, Crabtree MJ, Balligand JL, Casadei B. Regulation of endothelial nitric-oxide synthase (NOS) S-glutathionylation by neuronal NOS: evidence of a functional interaction between myocardial constitutive NOS isoforms. J Biol Chem. 2012 Dec 21;287(52):43665-73. doi: 10.1074/jbc.M112.412031. Epub 2012 Oct 22. PubMed PMID: 23091050; PubMed Central PMCID: PMC3527952. 6: Itzhak Y, Martin JL, Ail SF. nNOS inhibitors attenuate methamphetamine-induced dopaminergic neurotoxicity but not hyperthermia in mice. Neuroreport. 2000 Sep 11;11(13):2943-6. PubMed PMID: 11006970. 7: Pamenter ME, Go A, Fu Z, Powell FL. No evidence of a role for neuronal nitric oxide synthase in the nucleus tractus solitarius in ventilatory responses to acute or chronic hypoxia in awake rats. J Appl Physiol (1985). 2015 Mar 15;118(6):750-9. doi: 10.1152/japplphysiol.00333.2014. Epub 2015 Jan 8. PubMed PMID: 25571988; PubMed Central PMCID: PMC4360023. 8: Santamarta MT, Llorente J, Mendiguren A, Pineda J. Involvement of neuronal nitric oxide synthase in desensitisation of µ-opioid receptors in the rat locus coeruleus. J Psychopharmacol. 2014 Oct;28(10):903-14. doi: 10.1177/0269881114538542. Epub 2014 Jun 24. PubMed PMID: 24961237. 9: Homma K, Hayashi K, Wakino S, Tokuyama H, Kanda T, Tatematsu S, Hasegawa K, Fujishima S, Hori S, Saruta T, Itoh H. Rho-kinase contributes to pressure-induced constriction of renal microvessels. Keio J Med. 2014;63(1):1-12. Epub 2014 Jan 16. PubMed PMID: 24429483. 10: Li Y, Cui X, Xu W, Ohanjanian L, Sampath-Kumar H, Suffredini D, Moayeri M, Leppla S, Fitz Y, Eichacker PQ. Nitric oxide production contributes to Bacillus anthracis edema toxin-associated arterial hypotension and lethality: ex vivo and in vivo studies in the rat. Am J Physiol Heart Circ Physiol. 2016 Sep 1;311(3):H781-93. doi: 10.1152/ajpheart.00163.2016. Epub 2016 Jul 22. PubMed PMID: 27448553; PubMed Central PMCID: PMC5142181. 11: Trabace L, Cassano T, Tucci P, Steardo L, Kendrick KM, Cuomo V. The effects of nitric oxide on striatal serotoninergic transmission involve multiple targets: an in vivo microdialysis study in the awake rat. Brain Res. 2004 May 22;1008(2):293-8. PubMed PMID: 15145769. 12: Furfine ES, Harmon MF, Paith JE, Knowles RG, Salter M, Kiff RJ, Duffy C, Hazelwood R, Oplinger JA, Garvey EP. Potent and selective inhibition of human nitric oxide synthases. Selective inhibition of neuronal nitric oxide synthase by S-methyl-L-thiocitrulline and S-ethyl-L-thiocitrulline. J Biol Chem. 1994 Oct 28;269(43):26677-83. PubMed PMID: 7523410. 13: Sternesjö J, Welsh N, Sandler S. S-methyl-L-thiocitrulline counteracts interleukin 1 beta induced suppression of pancreatic islet function in vitro, but does not protect against multiple low-dose streptozotocin-induced diabetes in vivo. Cytokine. 1997 May;9(5):352-9. PubMed PMID: 9195135. 14: Smith CA, Santymire B, Erdely A, Venkat V, Losonczy G, Baylis C. Renal nitric oxide production in rat pregnancy: role of constitutive nitric oxide synthases. Am J Physiol Renal Physiol. 2010 Oct;299(4):F830-6. doi: 10.1152/ajprenal.00300.2010. Epub 2010 Jul 14. PubMed PMID: 20630934; PubMed Central PMCID: PMC2957259. 15: Levine DZ, Iacovitti M, Robertson SJ, Mokhtar GA. Modulation of single-nephron GFR in the db/db mouse model of type 2 diabetes mellitus. Am J Physiol Regul Integr Comp Physiol. 2006 Apr;290(4):R975-81. Epub 2005 Dec 8. PubMed PMID: 16339386. 16: Shabeeh H, Seddon M, Brett S, Melikian N, Casadei B, Shah AM, Chowienczyk P. Sympathetic activation increases NO release from eNOS but neither eNOS nor nNOS play an essential role in exercise hyperemia in the human forearm. Am J Physiol Heart Circ Physiol. 2013 May;304(9):H1225-30. doi: 10.1152/ajpheart.00783.2012. Epub 2013 Feb 22. PubMed PMID: 23436331; PubMed Central PMCID: PMC3652092. 17: Levine DZ, Iacovitti M, Robertson SJ. Modulation of single-nephron GFR in the db/db mouse model of type 2 diabetes mellitus. II. Effects of renal mass reduction. Am J Physiol Regul Integr Comp Physiol. 2008 Jun;294(6):R1840-6. doi: 10.1152/ajpregu.00457.2007. Epub 2008 Apr 16. Erratum in: Am J Physiol Regul Integr Comp Physiol. 2009 Jan;296(1):R193. PubMed PMID: 18417648. 18: Shabeeh H, Melikian N, Dworakowski R, Casadei B, Chowienczyk P, Shah AM. Differential role of endothelial versus neuronal nitric oxide synthase in the regulation of coronary blood flow during pacing-induced increases in cardiac workload. Am J Physiol Heart Circ Physiol. 2013 May;304(9):H1277-82. doi: 10.1152/ajpheart.00927.2012. Epub 2013 Mar 11. PubMed PMID: 23479261; PubMed Central PMCID: PMC3652090. 19: Copp SW, Hirai DM, Sims GE, Fels RJ, Musch TI, Poole DC, Kenney MJ. Neuronal nitric oxide synthase inhibition and regional sympathetic nerve discharge: implications for peripheral vascular control. Respir Physiol Neurobiol. 2013 May 1;186(3):285-9. doi: 10.1016/j.resp.2013.02.021. Epub 2013 Feb 27. PubMed PMID: 23454026; PubMed Central PMCID: PMC3999663. 20: Zhang J, Xu M, Dence CS, Sherman EL, McCarthy TJ, Welch MJ. Synthesis, in vivo evaluation and PET study of a carbon-11-labeled neuronal nitric oxide synthase (nNOS) inhibitor S-methyl-L-thiocitrulline. J Nucl Med. 1997 Aug;38(8):1273-8. PubMed PMID: 9255165.