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C9419

Sigma-Aldrich

4-Chloro-D-phenylalanine

Synonym(s):

D-PCP, D-PCPA

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About This Item

Empirical Formula (Hill Notation):
C9H10ClNO2
CAS Number:
14091-08-8
Molecular Weight:
199.63
Beilstein/REAXYS Number:
2416151
MDL number:
MFCD00079675
UNSPSC Code:
12352200
PubChem Substance ID:
24892996

form

solid

technique(s)

ligand binding assay: suitable

storage temp.

−20°C

SMILES string

N[C@H](Cc1ccc(Cl)cc1)C(O)=O

InChI

1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1

InChI key

NIGWMJHCCYYCSF-MRVPVSSYSA-N

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Biochem/physiol Actions

4-Chloro-D-phenylalanine (D-PCP, D-Phe(4Cl)) is a component of the synthetic decapeptide SB-4-Chloro-D-phenylalanine. (D-PCP, D-Phe(4Cl)) is a component of the synthetic peptides SB-75/cetrorelix, a Gonadotropin Releasing Hormone (GnRH) antagonist, and of the VIP receptor antagonist (4Cl-D-Phe(6),Leu(17))-VIP.

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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S Kordasti et al.
Gut, 53(7), 952-957 (2004-06-15)
The mechanisms underlying intestinal secretion in rotavirus diarrhoea remain to be established. We previously reported that rotavirus evokes intestinal fluid and electrolyte secretion by activation of the enteric nervous system. We now report that antagonists for the 5-hydroxytryptamine 3 receptor
J Pinski et al.
International journal of peptide and protein research, 45(5), 410-417 (1995-05-01)
The objective of this study was to examine the in vivo and in vitro gonadotropin-inhibiting potencies, edematogenic activities and the receptor binding affinities of the D-Cit6, D,L-Cit6 and L-Cit6 forms of the LH-RH antagonist Cetrorelix (SB-75) [Ac-D-Nal(2)1,D-Phe(4Cl)2,D-Pal(3)3,D-Cit6,D-Ala10]LH- RH. In order
T Yano et al.
Proceedings of the National Academy of Sciences of the United States of America, 91(15), 7090-7094 (1994-07-19)
Female athymic nude mice bearing xenografts of OV-1063 human epithelial ovarian cancer cell line were treated with potent luteinizing hormone (LH)-releasing hormone (LH-RH) antagonist SB-75 (Cetrorelix; [Ac-D-Nal(2)1, D-Phe(4 CI)2, D-Pal(3)3, D-Cit6, D-Ala10]LH-RH in which Ac-D-Nal(2) = N-acetyl-3-(2-naphthyl)-D-alanine, D-Phe(4CI) = 4-chloro-D-phenylalanine
J Horvath et al.
International journal of oncology, 6(5), 969-975 (1995-05-01)
The effects of luteinizing hormone-releasing hormone (LH-RH), and LH-RH antagonist Cetrorelix, (SB-75, [Ac-D-Nal(2)(1),D-Phe(4-Cl)(2),D-Pal(3)(3),D-Cit(6),D-Ala(10)]LH-RH) on cell growth and the production of hCG and cAMP in JAR human choriocarcinoma cells were examined in vitro. Both LH-RH and its antagonist SE-75, at 1
Takeharu Niioka et al.
Archives of oral biology, 54(10), 909-916 (2009-08-04)
The parasympathetic vasodilatory fibres are known to innervate vessels in a rat masseter muscle via both cholinergic and non-cholinergic mechanisms. However, the non-cholinergic mechanisms are still unclear. Recently, vasoactive intestinal polypeptide (VIP) was convincingly shown to be involved in the
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