Chemistry:Sergolexole

Sergolexole
Identifiers
	IUPAC name (4-methoxycyclohexyl) (6aR,9R,10aR)-7-methyl-4-propan-2-yl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carboxylate;
CAS Number	108674-86-8 ;
PubChem CID	60262;
UNII	J6TGA89COP;
Chemical and physical data
Formula	C26H36N2O3
Molar mass	424.585 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)N1C=C2C[C@@H]3[C@H](C[C@H](CN3C)C(=O)OC4CCC(CC4)OC)C5=C2C1=CC=C5;
	InChI InChI=1S/C26H36N2O3/c1-16(2)28-15-17-13-24-22(21-6-5-7-23(28)25(17)21)12-18(14-27(24)3)26(29)31-20-10-8-19(30-4)9-11-20/h5-7,15-16,18-20,22,24H,8-14H2,1-4H3/t18-,19?,20?,22-,24-/m1/s1; Key:RJBJIKXTJIZONR-FTNAIZGWSA-N;

Short description: Chemical compound

Sergolexole (developmental code name LY-281,067) is an ergoline derivative which acts as a selective antagonist of the serotonin 5-HT₂ receptors. It has been used for various research applications, but was never developed for medical use.^[1]^[2]^[3]

References

↑ "Preclinical pharmacology of a new serotonergic receptor antagonist, LY281067". The Journal of Pharmacology and Experimental Therapeutics 244 (1): 106–12. January 1988. PMID 3335993.
↑ "5-Hydroxytryptamine2 receptor antagonist activity of the acid metabolite (1-isopropyl dihydrolysergic acid) of the ergoline ester, sergolexole (LY281067)". The Journal of Pharmacology and Experimental Therapeutics 251 (3): 1006–11. December 1989. PMID 2600800.
↑ "Vascular smooth muscle proliferation: synergistic interaction between serotonin and low density lipoproteins". Journal of the American College of Cardiology 34 (5): 1644–51. November 1999. doi:10.1016/s0735-1097(99)00349-6. PMID 10551718.

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v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergotamine Ergotoxine Ergovaline Lisuride LSD LSH Lysergic Acid Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Lysergic Acid Methyl Ester Lysergol Mesulergine Metergoline Methergine (Methylergometrine, Methylergonovine, Methylergobasine) Methysergide Pergolide Syntometrine
Psychedelic lysergamides	1B-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD DAL DAM-57 ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Methylergonovine MIPLA MLD-41 PARGY-LAD PRO-LAD
clavines	agroclavine elymoclavine lysergol festuclavine fumigaclavine A fumigaclavine B fumigaclavine C
Other ergolines	Ergoline
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)

Identifiers

IUPAC name (4-methoxycyclohexyl) (6aR,9R,10aR)-7-methyl-4-propan-2-yl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carboxylate
CAS Number	108674-86-8^Y
PubChem CID	60262
UNII	J6TGA89COP
Chemical and physical data
Formula	C₂₆H₃₆N₂O₃
Molar mass	424.585 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C)N1C=C2C[C@@H]3[C@H](C[C@H](CN3C)C(=O)OC4CCC(CC4)OC)C5=C2C1=CC=C5
InChI InChI=1S/C26H36N2O3/c1-16(2)28-15-17-13-24-22(21-6-5-7-23(28)25(17)21)12-18(14-27(24)3)26(29)31-20-10-8-19(30-4)9-11-20/h5-7,15-16,18-20,22,24H,8-14H2,1-4H3/t18-,19?,20?,22-,24-/m1/s1 Key:RJBJIKXTJIZONR-FTNAIZGWSA-N