S(+)-N,N-DIETHYL-N'([8ALPHA]-6-METHYLERGOLIN-8-YL)UREA

Product NameS(+)-N,N-DIETHYL-N'([8ALPHA]-6-METHYLERGOLIN-8-YL)UREA
CAS37686-84-3
MFC20H28N4O
MW340.46
EINECS253-624-2
MOL File37686-84-3.mol

Chemical Properties

Melting point	203-204° (dec); mp 205-207° (dec) (Cerny)
alpha	D20 +30° (c = 1 in pyridine); D20 +29.0° (c = 0.2 in pyridine)
Boiling point	476.25°C (rough estimate)
Density	1.1056 (rough estimate)
refractive index	1.6620 (estimate)
storage temp.	2-8°C
solubility	DMSO: soluble
form	solid
pka	13.60±0.20(Predicted)
color	white
Stability	Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.
InChIKey	JOAHPSVPXZTVEP-IHMLPVBLNA-N
SMILES	C12=C3C=CC=C1[C@@]1([H])C[C@@H](CN(C)[C@]1([H])CC2=CN3)NC(=O)N(CC)CC \|&1:6,9,13,r\|

Safety Information

Hazard Codes	T
Risk Statements	23/24/25
Safety Statements	36/37/39-45
RIDADR	UN 2811 6.1/PG 2
WGK Germany	3
RTECS	YS9378700
Toxicity	LD50 oral in rat: 100mg/kg

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

Terguride (37686-84-3) is a semi-synthetic ergoline derivative which acts as a partial dopamine D2 agonist and 5HT2B/2C receptor antagonist. Displays antiparkinsonian effects in MPTP-treated cynomolgus monkeys.1Partial agonist at recruitment of β-arrestin2 to the D2 receptor.2 Terguride ameliorates monocrotaline-induced pulmonary hypertension in rats.3

Uses

An ergot alkaloid derivative that acts as a partial dopamine D2-receptor agonist. An anti-hyperprolactinemia agent.

Definition

ChEBI: Terguride is an organic molecular entity.

in vivo

TDHL abolished 5-HT-induced pulmonary vasoconstriction. Chronic terguride treatment prevented dose-dependently the development and progression of MCT-induced PAH in rats^[1]. In reserpinized rats, terguride at 0.03 mg/kg, p.o. significantly reduces the serum prolactin (PRL) level. In rats bearing estrogen-induced pituitary prolactinoma, chronic terguride induces shrinkage of the prolactinoma as well as reduction of the high serum PRL level. In lactating rats, terguride (1.0 mg/kg, s.c.) reduces milk production in the mammary gland^[2].

References

[1] TETSUO AKAI MS, PHD. Effects of terguride, a partial D2 agonist, on MPTP-lesioned parkinsonian cynomolgus monkeys[J]. Annals of Neurology, 1993, 33 5: 507-511. DOI:10.1002/ana.410330515
[2] IB V. KLEWE . Recruitment of β-arrestin2 to the dopamine D2 receptor: Insights into anti-psychotic and anti-parkinsonian drug receptor signaling[J]. Neuropharmacology, 2008, 54 8: Pages 1215-1222. DOI:10.1016/j.neuropharm.2008.03.015
[3] R DUMITRASCU. Terguride ameliorates monocrotaline-induced pulmonary hypertension in rats.[J]. European Respiratory Journal, 2011, 37 5: 1104-1118. DOI:10.1183/09031936.00126010

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