Metergoline

Metergoline
Clinical data
ATC code	G02CB05 (WHO) ;
Identifiers
	IUPAC name {[(8β)-1,6-dimethylergolin-8-yl]methyl}carbamate;
CAS Number	17692-51-2 ;
PubChem CID	28693;
IUPHAR/BPS	133;
ChemSpider	26687 ;
UNII	1501393LY5;
ChEMBL	ChEMBL19215 ;
CompTox Dashboard (EPA)	DTXSID5042584 ;
ECHA InfoCard	100.037.881
Chemical and physical data
Formula	C25H29N3O2
Molar mass	403.526 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OCc1ccccc1)NC[C@@H]3C[C@@H]4c5cccc2c5c(cn2C)C[C@H]4N(C3)C;
	InChI InChI=1S/C25H29N3O2/c1-27-14-18(13-26-25(29)30-16-17-7-4-3-5-8-17)11-21-20-9-6-10-22-24(20)19(12-23(21)27)15-28(22)2/h3-10,15,18,21,23H,11-14,16H2,1-2H3,(H,26,29)/t18-,21+,23+/m0/s1 ; Key:WZHJKEUHNJHDLS-QTGUNEKASA-N ;
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Metergoline is a psychoactive drug of the ergoline chemical class which acts as a ligand for various serotonin and dopamine receptors.[1][2]

References

Hamon M, Mallat M, Herbet A, et al. (February 1981). "[3H]Metergoline: a new ligand of serotonin receptors in the rat brain". Journal of Neurochemistry. 36 (2): 613–26. doi:10.1111/j.1471-4159.1981.tb01634.x. PMID 7463079.
Miller KJ, King A, Demchyshyn L, Niznik H, Teitler M (1992). "Agonist activity of sumatriptan and metergoline at the human 5-HT_1D beta receptor: further evidence for a role of the 5-HT_1D receptor in the action of sumatriptan". Eur. J. Pharmacol. 227 (1): 99–102. doi:10.1016/0922-4106(92)90149-P. PMID 1330643.

Metergoline at the US National Library of Medicine Medical Subject Headings (MeSH)

Tocolytics/labor repressants (G02CA)
β₂ adrenoreceptor agonists	Buphenine Fenoterol Hexoprenaline Ritodrine Terbutaline
Oxytocin antagonists	Atosiban
NSAIDs	Indometacin
Calcium channel blockers	Nifedipine
Myosin inhibitors	Magnesium sulfate

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 LY-215,840 LSH Lysergic Acid Lysergic Acid Methyl Ester Lysergol Mesulergine Metergoline Methergine (Methylergometrine, Methylergonovine, Methylergobasine) Methysergide Sergolexole Syntometrine
Psychedelic lysergamides	1B-LSD 1cP-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 Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide LSD Methylergonovine MIPLA MLD-41 PARGY-LAD PRO-LAD
Clavines	Agroclavine Elymoclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C
Other ergolines	Ergoline Lergotrile Pergolide
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)