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;
CompTox Dashboard (EPA)	DTXSID10148700 ;
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;

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

^ Cohen ML, Fuller RW, Kurz KD, Parli CJ, Mason NR, Meyers DB, et al. (January 1988). "Preclinical pharmacology of a new serotonergic receptor antagonist, LY281067". The Journal of Pharmacology and Experimental Therapeutics. 244 (1): 106–12. PMID 3335993.
^ Cohen ML, Parli CJ, Fuller RW (December 1989). "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. PMID 2600800.
^ Koba S, Pakala R, Watanabe T, Katagiri T, Benedict CR (November 1999). "Vascular smooth muscle proliferation: synergistic interaction between serotonin and low density lipoproteins". Journal of the American College of Cardiology. 34 (5): 1644–51. doi:10.1016/s0735-1097(99)00349-6. PMID 10551718. S2CID 24224564.

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[1] Cohen ML, Fuller RW, Kurz KD, Parli CJ, Mason NR, Meyers DB, et al. (January 1988). "Preclinical pharmacology of a new serotonergic receptor antagonist, LY281067". The Journal of Pharmacology and Experimental Therapeutics. 244 (1): 106–12. PMID 3335993.

[Cohen_1989-2] Cohen ML, Parli CJ, Fuller RW (December 1989). "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. PMID 2600800.

[3] Koba S, Pakala R, Watanabe T, Katagiri T, Benedict CR (November 1999). "Vascular smooth muscle proliferation: synergistic interaction between serotonin and low density lipoproteins". Journal of the American College of Cardiology. 34 (5): 1644–51. doi:10.1016/s0735-1097(99)00349-6. PMID 10551718. S2CID 24224564.

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v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromerguride (2-bromolisuride) 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 Ergostine Ergotamine Ergotoxine Ergovaline Fludihydroergotamine Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mergocriptine Mesulergine Metergoline Metergotamine MIPLA Methysergide Propisergide Sergolexole
Psychedelic lysergamides	1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD (lysergide) LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Methylergometrine (Methylergonovine, Methylergobasine) MIPLA MLD-41 PARGY-LAD PRO-LAD
Clavines	9-Deacetoxyfumigaclavine C Agroclavine Chanoclavine Chanoclavine II Costaclavin Cycloclavine Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Paliclavine Penniclavine Setoclavine
Other ergolines	Acetergamine Brazergoline Cianergoline CY-208,243 Delergotrile Disulergine Dosergoside Ergoline Etisulergine Lergotrile Nicergoline Pergolide Proterguride Romergoline Terguride Tiomergine Voxergolide
Related compounds	Adrogolide Naxagolide Quinagolide
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)