4-Chloro-DL-phenylalanine methyl ester hydrochloride
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4-Chloro-DL-phenylalanine methyl ester hydrochloride

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4-Chloro-DL-phenylalanine methyl ester hydrochloride is a tryptophan hydroxylase (TPH) inhibitor and a serotonin synthesis inhibitor. 4-Chloro-DL-phenylalanine methyl ester hydrochloride is also known to induce memory deficits in rats.

Category
DL-Amino Acids
Catalog number
BAT-007860
CAS number
14173-40-1
Molecular Formula
C10H12ClNO2·HCl
Molecular Weight
250.12
4-Chloro-DL-phenylalanine methyl ester hydrochloride
IUPAC Name
methyl 2-amino-3-(4-chlorophenyl)propanoate;hydrochloride
Synonyms
DL-Phe(4-Cl)-OMe HCl; p-Chloro-DL-Phe-OMe HCl; (RS)-2-Amino-3-(4-chlorophenyl)propionic acid methyl ester hydrochloride; methyl 2-amino-3-(4-chlorophenyl)propanoate hydrochloride; H-DL-Phe(4-Cl)-OMe HCl; DL-p-Chlorophenylalanine methyl ester hydrochloride; DL-4-Chlorophenylalanine methyl ester hydrochloride; H-p-Chloro-D-Phe-OMe HCl
Related CAS
23434-96-0 (free base)
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
g/cm3
Melting Point
176-190 °C
Boiling Point
296.3 °C at 760 mmHg
Storage
Store at -20°C
InChI
InChI=1S/C10H12ClNO2.ClH/c1-14-10(13)9(12)6-7-2-4-8(11)5-3-7;/h2-5,9H,6,12H2,1H3;1H
InChI Key
GCBCWTWQAFLKJG-UHFFFAOYSA-N
Canonical SMILES
COC(=O)C(CC1=CC=C(C=C1)Cl)N.Cl
1.Synthesis and biological evaluation of new 1,3-thiazolidine-4-one derivatives of nitro-l-arginine methyl ester.
Pânzariu AT1, Apotrosoaei M1, Vasincu IM1, Drăgan M1, Constantin S1, Buron F2, Routier S2, Profire L1, Tuchilus C3. Chem Cent J. 2016 Feb 4;10:6. doi: 10.1186/s13065-016-0151-6. eCollection 2016.
BACKGROUND: l-Arginine is a semi-essential aminoacid with important role in regulation of physiological processes in humans. It serves as precursor for the synthesis of proteins and is also substrate for different enzymes such as nitric oxide synthase. This amino-acid act as free radical scavenger, inhibits the activity of pro-oxidant enzymes and thus acts as an antioxidant and has also bactericidal effect against a broad spectrum of bacteria.
2.Protective effect of zingerone on increased vascular contractility in diabetic rat aorta.
Ghareib SA1, El-Bassossy HM2, Elberry AA3, Azhar A4, Watson ML5, Banjar ZM6, Alahdal AM7. Eur J Pharmacol. 2016 Mar 25. pii: S0014-2999(16)30176-5. doi: 10.1016/j.ejphar.2016.03.046. [Epub ahead of print]
The aim of the present study was to investigate the effect and possible mechanism of action of zingerone, the main constituent of ginger, on vascular reactivity in isolated aorta from diabetic rats. The results show that incubation of aortae with zingerone alleviates the exaggerated vasoconstriction of diabetic aortae to phenylephrine, as well as the impaired relaxatory response to acetylcholine in a concentration-dependent manner. Furthermore, Zingerone directly relax phenylephrine-precontracted aortae. The vasorelaxatory response is significantly attenuated by the nitric oxide synthase inhibitor Nω-nitro-l-arginine methyl ester hydrochloride and the guanylate cyclase inhibitor methylene blue but no effect of either the potassium channels blocker tetraethylammonium chloride, or the cyclooxygenase inhibitor indomethacin was observed. Zingerone had no effect on advanced glycation end product formation as well. In conclusion, zingerone ameliorates enhanced vascular contraction in diabetic aortae which may be mediated by its vasodilator effect through NO- and guanylate cyclase stimulation.
3.CD70 Exacerbates Blood Pressure Elevation and Renal Damage in Response to Repeated Hypertensive Stimuli.
Itani HA1, Xiao L1, Saleh MA1, Wu J1, Pilkinton MA1, Dale BL1, Barbaro NR1, Foss JD1, Kirabo A1, Montaniel KR1, Norlander AE1, Chen W1, Sato R1, Navar LG1, Mallal SA1, Madhur MS1, Bernstein KE1, Harrison DG2. Circ Res. 2016 Apr 15;118(8):1233-43. doi: 10.1161/CIRCRESAHA.115.308111. Epub 2016 Mar 17.
RATIONALE: Accumulating evidence supports a role of adaptive immunity and particularly T cells in the pathogenesis of hypertension. Formation of memory T cells, which requires the costimulatory molecule CD70 on antigen-presenting cells, is a cardinal feature of adaptive immunity.
4.Effects of midodrine and L-NAME on systemic and cerebral hemodynamics during cognitive activation in spinal cord injury and intact controls.
Wecht JM1, Weir JP2, Radulovic M3, Bauman WA3. Physiol Rep. 2016 Feb;4(3). pii: e12683. doi: 10.14814/phy2.12683.
We previously showed that increases in mean arterial pressure (MAP) following administration of midodrine hydrochloride (MH) and nitro-L-arginine methyl ester (L-NAME) resulted in increased mean cerebral blood flow velocity (MFV) during head-up tilt in hypotensive individuals with spinal cord injury (SCI) and question if this same association was evident during cognitive activation. Herein, we report MAP and MFV during two serial subtraction tasks (SSt) given before (predrug) and after (postdrug) administration of MH; (10 mg), L-NAME (1 mg/kg) or no drug (ND) in 15 subjects with SCI compared to nine able-bodied (AB) controls. Three-way factorial analysis of variance (ANOVA) models were used to determine significant main and interaction effects for group (SCI, AB), visit (MH, L-NAME, ND), and time (predrug, postdrug) for MAP and MFV during the two SSt. The three-way interaction was significant for MAP (F = 4.262; P = 0.020); both MH (30 ± 26 mmHg; P < 0.
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