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L4513

Sigma-Aldrich

[des-Gly10, D-Ala6]-LH-RH ethylamide acetate salt hydrate

≥97% (HPLC), powder

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Empirical Formula (Hill Notation):
C56H78N16O12 · xC2H4O2 · yH2O
Molecular Weight:
1167.32 (anhydrous free base basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

Assay

≥97% (HPLC)

form

powder

UniProt accession no.

storage temp.

−20°C

SMILES string

O.CC(O)=O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H](CO)NC(=O)[C@H](Cc3c[nH]c4ccccc34)NC(=O)[C@H](Cc5c[nH]cn5)NC(=O)[C@@H]6CCC(=O)N6

InChI

1S/C56H78N16O12.C2H4O2.H2O/c1-5-60-54(83)45-13-9-21-72(45)55(84)39(12-8-20-61-56(57)58)66-50(79)40(22-30(2)3)67-47(76)31(4)64-49(78)41(23-32-14-16-35(74)17-15-32)68-53(82)44(28-73)71-51(80)42(24-33-26-62-37-11-7-6-10-36(33)37)69-52(81)43(25-34-27-59-29-63-34)70-48(77)38-18-19-46(75)65-38;1-2(3)4;/h6-7,10-11,14-17,26-27,29-31,38-45,62,73-74H,5,8-9,12-13,18-25,28H2,1-4H3,(H,59,63)(H,60,83)(H,64,78)(H,65,75)(H,66,79)(H,67,76)(H,68,82)(H,69,81)(H,70,77)(H,71,80)(H4,57,58,61);1H3,(H,3,4);1H2/t31-,38+,39+,40+,41+,42+,43+,44+,45+;;/m1../s1

InChI key

YEEHIOYEWOESQR-PFHUABGLSA-N

Gene Information

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This Item
L1898L7134L9761
[D-Trp6]-LH-RH ≥97% (HPLC), powder

Sigma-Aldrich

L9761

[D-Trp6]-LH-RH

form

powder

form

-

form

powder

form

powder

UniProt accession no.

P01148, P13562, P30968, Q01776

UniProt accession no.

P01148

UniProt accession no.

P01148

UniProt accession no.

P01148, P30968

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

Gene Information

mouse ... GNRH1(2796), GNRHR(2798)
rat ... GNRH1(14714), GNRHR(14715)

Gene Information

human ... GNRH1(2796)

Gene Information

human ... GNRH1(2796)

Gene Information

human ... GNRH1(2796), GNRHR(2798)

Amino Acid Sequence

Glp-His-Trp-Ser-Tyr-Ala-Leu-Arg-Pro-NHEt

Application

[des-Gly10, D-Ala6]-LH-RH ethylamide acetate salt hydrate has been used:
  • as an luteinizing hormone-releasing hormone (LHRH) agonist to synchronize a cohort of females rats
  • to synchronize naturally cycling rats
  • to induce ovulation as a gonadotropin-releasing hormone (GnRH) analogue and as a supplement in Galap extender to dilute qualified ejaculate

Biochem/physiol Actions

Potent LH-RH agonist in rats and mice; reversibly delays sexual maturation in rats, stimulates spawning activity in fish. GnRH ( gonadotropin-releasing hormone, Glp-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2), which is also referred as LHRH (luteinizing hormone-releasing hormone) or gonadorelin, is crucial for mammalian reproduction and is released from hypothalamic neurons. It is responsible for the secretion of gonadotropins, luteinizing hormone (LH) and follicle-stimulating hormone (FSH), from the pituitary glands. Mutations in GnRH are associated with normosmic congenital hypogonadotropic hypogonadism.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Repr. 1B

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Kempinas WG, et al.
Biology of Reproduction, 59(4), 897-904 (1998)
W S Yeung et al.
General and comparative endocrinology, 89(3), 323-332 (1993-03-01)
The effects of ovine luteinizing hormone (oLH) and a synthetic analog of luteinizing hormone releasing hormone, des-Gly10 [D-Ala6]-LHRH ethylamide acetate salt (LHRH-A), on gonadal development and on in vitro steroidogenesis in the female phase of the protogynous sex-reversing Monopterus albus
Emmet L Guy et al.
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Asynchrony of gamete release is problematic in amphibian captive breeding programs but can be overcome by short-term storage of spermatozoa. Hormonally induced sperm from the model species Anaxyrus fowleri were used to determine storage conditions for optimal fertilisation capacity. Sperm

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