Mesulergine

Mesulergine
Clinical data
Other names	CU-32085
Identifiers
	IUPAC name N'-(1,6-dimethylergolin-8α-yl)-N,N-dimethylsulfamide;
CAS Number	64795-35-3 ;
PubChem CID	68848;
IUPHAR/BPS	206; [3H]mesulergine: 232;
ChemSpider	62081 ;
UNII	SML95FK06I;
ChEBI	CHEBI:73378 ;
ChEMBL	ChEMBL462903 ;
CompTox Dashboard (EPA)	DTXSID3046324 ;
Chemical and physical data
Formula	C18H26N4O2S
Molar mass	362.49 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(=O)(N(C)C)N[C@H]2C[C@@H]3c4cccc1c4c(cn1C)C[C@H]3N(C2)C;
	InChI InChI=1S/C18H26N4O2S/c1-20(2)25(23,24)19-13-9-15-14-6-5-7-16-18(14)12(10-21(16)3)8-17(15)22(4)11-13/h5-7,10,13,15,17,19H,8-9,11H2,1-4H3/t13-,15+,17+/m0/s1 ; Key:JLVHTNZNKOSCNB-YSVLISHTSA-N ;
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Mesulergine (INNTooltip International Nonproprietary Name) (developmental code name CU-32085) is a drug of the ergoline group which was never marketed.^[1]^[2] It acts on serotonin and dopamine receptors.^[3]^[4] Specifically, it is an agonist of dopamine D₂-like receptors and serotonin 5-HT₆ receptors and an antagonist of serotonin 5-HT_2A, 5-HT_2B, 5-HT_2C, and 5-HT₇ receptors.^{[citation needed]}. It also has affinity for the 5-HT_1A, 5-HT_1B, 5-HT_1D, 5-HT_1F, and 5-HT_5A receptors.^[5] The compound had entered clinical trials for the treatment of Parkinson's disease; however, further development was halted due to adverse histological abnormalities in rats.^[6] It was also investigated for the treatment of hyperprolactinemia (high prolactin levels).^[7]

References

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 776–. ISBN 978-1-4757-2085-3.
^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 177–. ISBN 978-94-011-4439-1.
^ Closse A (May 1983). "[3H]Mesulergine, a selective ligand for serotonin-2 receptors". Life Sciences. 32 (21): 2485–2495. doi:10.1016/0024-3205(83)90375-2. PMID 6855451.
^ Markstein R (November 1983). "Mesulergine and its 1,20-N,N-bidemethylated metabolite interact directly with D1- and D2-receptors". European Journal of Pharmacology. 95 (1–2): 101–107. doi:10.1016/0014-2999(83)90272-8. PMID 6230246.
^ National Institute of Mental Health. PDSD Ki Database (Internet). ChapelHill (NC): University of North Carolina. Available from: "PDSP Database - UNC". Archived from the original on 12 April 2021.
^ Dupont E, Mikkelsen B, Jakobsen J (April 1986). "Mesulergine in early Parkinson's disease: a double blind controlled trial". Journal of Neurology, Neurosurgery, and Psychiatry. 49 (4): 390–395. doi:10.1136/jnnp.49.4.390. PMC 1028763. PMID 3517235.
^ Bankowski BJ, Zacur HA (June 2003). "Dopamine agonist therapy for hyperprolactinemia". Clinical Obstetrics and Gynecology. 46 (2): 349–362. doi:10.1097/00003081-200306000-00013. PMID 12808385. S2CID 29368668.

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[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 776–. ISBN 978-1-4757-2085-3.

[MortonHall2012-2] Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 177–. ISBN 978-94-011-4439-1.

[pmid6855451-3] Closse A (May 1983). "[3H]Mesulergine, a selective ligand for serotonin-2 receptors". Life Sciences. 32 (21): 2485–2495. doi:10.1016/0024-3205(83)90375-2. PMID 6855451.

[pmid6230246-4] Markstein R (November 1983). "Mesulergine and its 1,20-N,N-bidemethylated metabolite interact directly with D1- and D2-receptors". European Journal of Pharmacology. 95 (1–2): 101–107. doi:10.1016/0014-2999(83)90272-8. PMID 6230246.

[PDSDKiDB-5] National Institute of Mental Health. PDSD Ki Database (Internet). ChapelHill (NC): University of North Carolina. Available from: "PDSP Database - UNC". Archived from the original on 12 April 2021.

[pmid3517235-6] Dupont E, Mikkelsen B, Jakobsen J (April 1986). "Mesulergine in early Parkinson's disease: a double blind controlled trial". Journal of Neurology, Neurosurgery, and Psychiatry. 49 (4): 390–395. doi:10.1136/jnnp.49.4.390. PMC 1028763. PMID 3517235.

[pmid12808385-7] Bankowski BJ, Zacur HA (June 2003). "Dopamine agonist therapy for hyperprolactinemia". Clinical Obstetrics and Gynecology. 46 (2): 349–362. doi:10.1097/00003081-200306000-00013. PMID 12808385. S2CID 29368668.

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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)