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ChemicalBook--->CAS DataBase List--->37686-84-3

37686-84-3

37686-84-3 Structure

37686-84-3 Structure
IdentificationBack Directory
[Name]

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

37686-84-3
[Synonyms]

TDHL
Teluron
dironyl
tergurid
terguride
S(+)-TERGURIDE
R-(+)-TERGURIDE
TRANS-DIHYDROLISURIDE
9,10a-Dihydrolisuride
Ergoline, urea deriv.
9,10α-Dihydrolisuride
(5R,8S,10R)-Terguride
(+)-(5R,8S,10R)-Terguride
9,10-alpha-dihydrolisuride
S(+)-TERGURIDE (5R, 8S, 10R)
Indolo[4,3-fg]quinoline, urea deriv.
1,1-Diethyl-3-(6-methylergolin-8α-yl)urea
6-Methyl-8a-(diethylcarbamoylamino)ergoline
6-Methyl-8α-(diethylcarbaMoylaMino)ergoline
N,N-Diethyl-N'-[(8α)-6-Methylergolin-8-yl]urea
Urea, N,N-diethyl-N'-[(8α)-6-methylergolin-8-yl]-
s(+)-n,n-diethyl-n'([8α]-6-methylergolin-8-yl)urea
N,N-Diethyl-N'-(D-6-methyl-10a-isoergolin-8-yl)urea
n,n-diethyl-n’-((8-alpha)-6-methylergolin-8-yl)-ure
N,N-Diethyl-N'-(D-6-Methyl-10α-isoergolin-8-yl)urea
1-((5r,8s,10r)-6-methyl-8-ergolinyl)-3,3-diethylurea
S(+)-N,N-DIETHYL-N'([8ALPHA]-6-METHYLERGOLIN-8-YL)UREA
Urea, N,N-diethyl-N'-[(8a)-6-methylergolin-8-yl]- (9CI)
S(+)-N,N-Diethyl-Nμ([8α]-6-methylergolin-8-yl)urea, S(+)-Terguride (5R, 8S, 10R)
1,1-Diethyl-3-((6aR,9S)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl)urea
[EINECS(EC#)]

253-624-2
[Molecular Formula]

C20H28N4O
[MDL Number]

MFCD00242729
[MOL File]

37686-84-3.mol
[Molecular Weight]

340.46
Chemical PropertiesBack Directory
[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.
Safety DataBack Directory
[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
Hazard InformationBack Directory
[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.1?Partial 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) Akai et al. (1993), Effects of terguride, a partial D2 agonist, on MPTP-lesioned parkinsonian cynomolgus monkeys; Ann. Neurol., 133 507 2) Klewe et al. (2008), Recruitment of beta-arrestin2 to the dopamine D2 receptor: insights into anti-psychotic and anti-parkinsonian drug receptor signaling; Neuropharmacology, 54 1215 3) Dumitrascu et al. (2011), Terguride ameliorates monocrotaline-induced pulmonary hypertension in rats; Eur. Respir. J., 37 1104
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