Short description: Chemical compound Methylergometrine Clinical data Trade names| Methergine Other names| Methylergonovine; methylergobasin; Methylergobasine; Methylergobrevin; d-Lysergic acid 1-butanolamide; N-[(2S)-1-Hydroxybutan-2-yl]-6-methyl-9,10-didehydroergoline-8β-carboxamide AHFS/Drugs.com| International Drug Names MedlinePlus| a601077 Pregnancy category| * Contraindicated Routes of administration| Oral ATC code| * G02AB01 (WHO) Legal status Legal status| * In general: ℞ (Prescription only) Pharmacokinetic data Metabolism| Liver Elimination half-life| 30–120 minutes Excretion| Mostly bile Identifiers IUPAC name * (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CAS Number| * 113-42-8 Y PubChem CID| * 8226 IUPHAR/BPS| * 150 ChemSpider| * 7933 N UNII| * W53L6FE61V ChEMBL| * ChEMBL1201356 N Chemical and physical data Formula| C20H25N3O2 Molar mass| 339.439 g·mol−1 3D model (JSmol)| * Interactive image Melting point| 172 °C (342 °F) Solubility in water| Insoluble mg/mL (20 °C) SMILES * CC[C@@H](CO)NC(=O)[C@@H]2/C=C1/c3cccc4N\C=C(\C[C@H]1N(C)C2)c34 InChI * InChI=1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1 N * Key:UNBRKDKAWYKMIV-QWQRMKEZSA-N N NY (what is this?) (verify) Methylergometrine, also known as methylergonovine and sold under the brand name Methergine, is a medication of the ergoline and lysergamide groups which is used as an oxytocic in obstetrics and in the treatment of migraine. It reportedly produces psychedelic effects similar to those of lysergic acid diethylamide (LSD) at high doses. It is on the World Health Organization's List of Essential Medicines.[1] ## Contents * 1 Medical uses * 1.1 Obstetric use * 1.2 Migraine * 2 Contraindications * 3 Side effects * 4 Interactions * 5 Pharmacology * 5.1 Pharmacodynamics * 6 Chemistry * 7 References ## Medical uses ### Obstetric use Methylergometrine is a smooth muscle constrictor that mostly acts on the uterus. It is most commonly used to prevent or control excessive bleeding following childbirth and spontaneous or elective abortion, and also to aid in expulsion of retained products of conception after a missed abortion (miscarriage in which all or part of the fetus remains in the uterus) and to help deliver the placenta after childbirth. It is available as tablets or injection (IM or IV) or in liquid form to be taken orally.[2][3][4] ### Migraine Methylergometrine is sometimes used for both prevention[5] and acute treatment[6] of migraine. It is an active metabolite of methysergide.[7] In the treatment of cluster headaches, methylergometrine has been initiated at a dose of 0.2 mg/day, rapidly increased to 0.2 mg three times per day, and increased to a maximum of 0.4 mg three times per day.[7] ## Contraindications Methylergometrine is contraindicated in patients with hypertension and pre-eclampsia.[2] It is also contraindicated in HIV positive patients taking protease inhibitors, delavirdine, and efavirenz (which is also an agonist at the 5-HT2A–mGlu2 receptor protomer and increases the chances of a patient experiencing hallucinations during methylergometrine therapy).[8] ## Side effects Adverse effects include:[2] * Nausea, vomiting, and diarrhea * Dizziness * Pulmonary hypertension * Coronary artery vasoconstriction * Severe systemic hypertension (especially in patients with pre-eclampsia) * Convulsions In excessive doses, methylergometrine can also lead to cramping, respiratory depression and coma.[2] ## Interactions Methylergometrine likely interacts with drugs that inhibit the liver enzyme CYP3A4, such as azole antifungals, macrolide antibiotics and many HIV drugs. It can also increase constriction of blood vessels caused by sympathomimetic drugs and other ergot alkaloids.[2] ## Pharmacology ### Pharmacodynamics Methylergometrine is an agonist or antagonist to serotonin, dopamine, and α-adrenergic receptors. Its specific binding and activation pattern on these receptors leads to a highly, if not completely, specific contraction of smooth uterus muscle via serotonin 5-HT2A receptors,[9] while blood vessels are affected to a lesser extent compared to other ergot alkaloids.[2] It has been found to interact with the serotonin 5-HT1A, 5-HT1B, 5-HT1E, 5-HT1F, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT5A, and 5-HT7 receptors.[10][11][12][13] Methylergometrine is a synthetic analogue of ergometrine, a psychedelic alkaloid found in ergot, and many species of morning glory. Methylergometrine is a member of the ergoline family and chemically similar to LSD, ergine, ergometrine, and lysergic acid. According to Jonathan Ott, methylergometrine produces LSD-like psychedelic effects at doses of 2 mg and above.[14] This can be attributed to due to its agonistic action at the 5-HT2A–mGlu2 receptor protomers. Clinical efficacy occurs around 200 µg, ten times lower than the hallucinogenic threshold.[14] Methylergometrine is an agonist of the serotonin 5-HT2B receptor and is maybe linked to cardiac valvulopathy.[15] Site | Affinity (Ki [nM]) | Efficacy (Emax [%]) | Action | | | 5-HT1A | 1.5–2.0 | ? | Full agonist 5-HT1B | 251 | ? | Full agonist 5-HT1D | 0.86–2.9 | 70 | Partial agonist 5-HT1E | 89 | ? | Full agonist 5-HT1F | 31 | ? | Full agonist 5-HT2A | 0.35–1.1 | ? | Full agonist 5-HT2B | 0.46–2.2 | ? | Full or partial agonist 5-HT2C | 4.6–43.7 | ? | Full agonist 5-HT3 | ? | – | – 5-HT5A | ? | 24.4[13] | Full agonist[13] 5-HT6 | ? | ? | Full agonist 5-HT7 | 11–52 | ? | Full agonist Notes: All sites are human except 5-HT1B (rat) and 5-HT7 (guinea pig).[10][11] ## Chemistry Methylergometrine, also known as d-lysergic acid 1-butanolamide, is a derivative of the ergoline and lysergamide classes and is structurally related to ergometrine (d-lysergic acid β-propanolamide) and lysergic acid diethylamide. ## References 1. ↑ World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. 2021. WHO/MHP/HPS/EML/2021.02. 2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 (in German) Austria-Codex (62nd ed.). Vienna: Österreichischer Apothekerverlag. 2007. pp. 5193–5. ISBN 978-3-85200-181-4. 3. ↑ (in German) Arzneimittelwirkungen (8th ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. 2001. p. 447. ISBN 3-8047-1763-2. 4. ↑ "Methergin" (in German). Fachinformation des Arzneimittel-Kompendium der Schweiz. http://www.kompendium.ch/Monographie.aspx?Id=c2bb9f2c-77a5-46c6-b9e5-dfd5b50e7c89&lang=de&MonType=fi. 5. ↑ "History of methysergide in migraine". Cephalalgia 28 (11): 1126–1135. November 2008. doi:10.1111/j.1468-2982.2008.01648.x. PMID 18644039. 6. ↑ "Efficacy and tolerability of intravenous methylergonovine in migraine female patients attending the emergency department: a pilot open-label study". Head & Face Medicine 5 (21): 21. November 2009. doi:10.1186/1746-160X-5-21. PMID 19895705. 7. ↑ 7.0 7.1 "Serotonergic agents in the management of cluster headache". Current Pain and Headache Reports 15 (2): 108–117. April 2011. doi:10.1007/s11916-011-0176-4. PMID 21271306. 8. ↑ "Methylergonovine Maleate Monograph for Professionals - Drugs.com". https://www.drugs.com/monograph/methylergonovine-maleate.html. 9. ↑ "Ergot Alkaloids and their Derivatives as Ligands for Serotoninergic, Dopaminergic, and Adrenergic Receptors". Ergot: the genus Claviceps. CRC Press. 1999. pp. 411–440. ISBN 978-905702375-0. 10. ↑ 10.0 10.1 Cite error: Invalid `` tag; no text was provided for refs named `PDSPKiDatabase` 11. ↑ 11.0 11.1 Cite error: Invalid `` tag; no text was provided for refs named `PDSPKiDatabase2` 12. ↑ Cite error: Invalid `` tag; no text was provided for refs named `OlivierWijngaarden1997` 13. ↑ 13.0 13.1 13.2 "Inactive and active state structures template selective tools for the human 5-HT5A receptor". Nature Structural & Molecular Biology 29 (7): 677–687. July 2022. doi:10.1038/s41594-022-00796-6. PMID 35835867. 14. ↑ 14.0 14.1 "Entheogenic (hallucinogenic) effects of methylergonovine". Journal of Psychedelic Drugs 12 (2): 165–166. 1980. doi:10.1080/02791072.1980.10471568. PMID 7420432. 15. ↑ "Safety Pharmacology assessment of drugs with biased 5-HT(2B) receptor agonism mediating cardiac valvulopathy". Journal of Pharmacological and Toxicological Methods 69 (2): 150–161. 2014. doi:10.1016/j.vascn.2013.12.004. PMID 24361689. Medical uses * v * t * e Uterotonics/labor inducers/oxytocics (G02A) Cervical ripening| | Ergot alkaloids| * Acetergamine * Ergometrine# (Syntometrine) * Methylergometrine | Prostaglandins and analogues| * E: Misoprostol/E1# * Gemeprost/E1 * Dinoprostone/E2 * Sulprostone/E2 * F: Dinoprost/F2α * Carboprost/F2α Contraction induction| * Oxytocin# * Carbetocin * Demoxytocin * #WHO-EM * ‡Withdrawn from market * Clinical trials: * †Phase III * §Never to phase III * v * t * e Antimigraine preparations (N02C) Analgesic/abortive| | Serotonergics| | Ergolines| * Dihydroergotamine * Ergotamine * Methysergide * Lisuride | 5-HT1 agonists| | Triptans| * Almotriptan * Avitriptan * Eletriptan * Frovatriptan * Naratriptan * Rizatriptan * Sumatriptan * Zolmitriptan | Ditans| * Alniditan§ * Lasmiditan Others| * Dimetotiazine * Dotarizine * Iprazochrome * Oxetorone * Pizotifen CGRP-R antagonists| * Rimegepant * Ubrogepant Others| * Paracetamol# * Amidrine Prophylactic| | Calcium channel blockers| * Dotarizine * Lomerizine * Verapamil * Flunarizine | Progestogens| * Flumedroxone acetate Sympatholytics| * Beta blockers * Propranolol# * Timolol * Clonidine Tricyclic antidepressants| * Amitriptyline * Nortriptyline * Imipramine Anticonvulsants| * Carbamazepine * Oxcarbazepine * Topiramate * Valproate Anti-CGRP/CGRP-R mAbs| * Eptinezumab * Erenumab * Fremanezumab * Galcanezumab * #WHO-EM * ‡Withdrawn from market * Clinical trials: * †Phase III * §Never to phase III * v * t * e Hallucinogens Psychedelics (5-HT2A agonists)| | Benzofurans| * 2C-B-FLY * 2CBFly-NBOMe * 5-MeO-BFE * 5-MeO-DiBF * Bromo-DragonFLY * F-2 * F-22 * TFMFly | Lyserg‐ amides| * 1B-LSD * 1P-ETH-LAD * 1P-LSD * 2-Butyllysergamide * 3-Pentyllysergamide * AL-LAD * ALD-52 * BU-LAD * Diallyllysergamide * Dimethyllysergamide * ECPLA * Ergometrine * ETH-LAD * IP-LAD * LAE-32 * LAMPA * LPD-824 * LSA * LSD * LSD-Pip * LSH * LSM-775 * LSZ * Methylergometrine * MIPLA * Methysergide * MLD-41 * PARGY-LAD * PRO-LAD Phenethyl‐ amines| | 2C-x| * 2C-B * 2C-B-AN * 2C-Bn * 2C-Bu * 2C-C * 2C-CN * 2C-CP * 2C-D * 2C-E * 2C-EF * 2C-F * 2C-G * 2C-G-1 * 2C-G-2 * 2C-G-3 * 2C-G-4 * 2C-G-5 * 2C-G-6 * 2C-G-N * 2C-H * 2C-I * 2C-iP * 2C-N * 2C-NH2 * 2C-O * 2C-O-4 * 2C-P * 2C-Ph * 2C-SE * 2C-T * 2C-T-2 * 2C-T-3 * 2C-T-4 * 2C-T-5 * 2C-T-6 * 2C-T-7 * 2C-T-8 * 2C-T-9 * 2C-T-10 * 2C-T-11 * 2C-T-12 * 2C-T-13 * 2C-T-14 * 2C-T-15 * 2C-T-16 * 2C-T-17 * 2C-T-18 * 2C-T-19 * 2C-T-20 * 2C-T-21 * 2C-T-22 * 2C-T-22.5 * 2C-T-23 * 2C-T-24 * 2C-T-25 * 2C-T-27 * 2C-T-28 * 2C-T-30 * 2C-T-31 * 2C-T-32 * 2C-T-33 * 2C-TFE * 2C-TFM * 2C-YN * 2C-V | 25x-NBx| | 25x-NB3OMe| * 25B-NB3OMe * 25C-NB3OMe * 25D-NB3OMe * 25E-NB3OMe * 25H-NB3OMe * 25I-NB3OMe * 25N-NB3OMe * 25P-NB3OMe * 25T2-NB3OMe * 25T4-NB3OMe * 25T7-NB3OMe * 25TFM-NB3OMe | 25x-NB4OMe| * 25B-NB4OMe * 25C-NB4OMe * 25D-NB4OMe * 25E-NB4OMe * 25H-NB4OMe * 25I-NB4OMe * 25N-NB4OMe * 25P-NB4OMe * 25T2-NB4OMe * 25T4-NB4OMe * 25T7-NB4OMe * 25TFM-NB4OMe 25x-NBF| * 25B-NBF * 25C-NBF * 25D-NBF * 25E-NBF * 25H-NBF * 25I-NBF * 25P-NBF * 25T2-NBF * 25T7-NBF * 25TFM-NBF 25x-NBMD| * 25B-NBMD * 25C-NBMD * 25D-NBMD * 25E-NBMD * 25F-NBMD * 25H-NBMD * 25I-NBMD * 25P-NBMD * 25T2-NBMD * 25T7-NBMD * 25TFM-NBMD 25x-NBOH| * 25B-NBOH * 25C-NBOH * 25CN-NBOH * 25D-NBOH * 25E-NBOH * 25F-NBOH * 25H-NBOH * 25I-NBOH * 25P-NBOH * 25T2-NBOH * 25T7-NBOH * 25TFM-NBOH 25x-NBOMe| * 25B-NBOMe * 25C-NBOMe * 25CN-NBOMe * 25D-NBOMe * 25E-NBOMe * 25F-NBOMe * 25G-NBOMe * 25H-NBOMe * 25I-NBOMe * 25iP-NBOMe * 25N-NBOMe * 25P-NBOMe * 25T2-NBOMe * 25T4-NBOMe * 25T7-NBOMe * 25TFM-NBOMe Atypical structures| * 25I-NB34MD * 2CBCB-NBOMe * 2CBFly-NBOMe * NBOMe-mescaline 3C-x| * 3C-AL * 3C-BZ * 3C-DFE * 3C-E * 3C-P 4C-x| * 4C-B * 4C-D * 4C-T-2 DOx| * DOT * DOB * DOC * DOEF * DOET * DOF * DOI * DOiPR * DOM * DON * DOPR * DOTFM * MEM HOT-x| * HOT-2 * HOT-7 * HOT-17 MDxx| * DMMDA * DMMDA-2 * Lophophine * MDA * MMDA * MMDA-2 * MMDA-3a * MMDMA Mescaline (subst.)| * 2-Bromomescaline * 3-TE * 4-TE * 3-TM * 4-TM * Allylescaline * Asymbescaline * Buscaline * Cyclopropylmescaline * Difluoromescaline * Difluoroescaline * Escaline * Fluoroproscaline * Isobuscaline * Isoproscaline * Jimscaline * Mescaline * Metaescaline * Methallylescaline * Proscaline * Thioproscaline * Trifluoroescaline * Trifluoromescaline TMAs| * TMA * TMA-2 * TMA-3 * TMA-4 * TMA-5 * TMA-6 Others| * 2C-B-BUTTERFLY * 2C-B-DragonFLY * 2CB-5-hemifly * 2-TOM * 5-TOET * 5-TOM * 2CB-Ind * 2CD-5EtO * BOB * BOD * βk-2C-B * βk-2C-I * DESOXY * DMCPA * DMBMPP * DOB-FLY * Fenfluramine * Ganesha * Macromerine * MMA * TCB-2 * TOMSO Piperazines| * BZP * pFPP Tryptamines| | alpha-alkyltryptamines| * 4,5-DHP-α-MT * 5-MeO-α-ET * 5-MeO-α-MT * α-ET * α-MT | x-DALT| * (Daltocin) 4-HO-DALT * (Daltacetin) 4-AcO-DALT * 5-MeO-DALT * DALT x-DET| * (Ethacetin) 4-AcO-DET * (Ethocin) 4-HO-DET * 5-MeO-DET * (T-9) DET * (Ethocybin) 4-PO-DET x-DiPT| * (Ipracetin) 4-AcO-DiPT * (Iprocin) 4-HO-DiPT * 5-MeO-DiPT * DiPT x-DMT| * 4,5-DHP-DMT * 2,N,N-TMT * 4-AcO-DMT * 4-HO-5-MeO-DMT * 4,N,N-TMT * 4-Propionyloxy-DMT * 5,6-diBr-DMT * 5-AcO-DMT * 5-Bromo-DMT * 5-MeO-2,N,N-TMT * 5-MeO-4,N,N-TMT * 5-MeO-α,N,N-TMT * 5-MeO-DMT * 5-N,N-TMT * 7,N,N-TMT * α,N,N-TMT * (Bufotenin) 5-HO-DMT * DMT * Norbaeocystin * (Psilocin) 4-HO-DMT * (Psilocybin) 4-PO-DMT x-DPT| * (Depracetin) 4-AcO-DPT * (Deprocin) 4-HO-DPT * 5-MeO-DPT * (The Light) DPT Ibogaine-related| * 18-MAC * 18-MC * Coronaridine * Ibogaine * Ibogamine * ME-18-MC * Noribogaine * Tabernanthine * Voacangine x-MET| * (Metocin) 4-HO-MET * (Metocetin) 4-AcO-MET * 5-MeO-MET * MET x-MiPT| * (Mipracetin) 4-AcO-MiPT * (Miprocin) 4-HO-MiPT * 5-Me-MiPT * (Moxy) 5-MeO-MiPT * MiPT Others| * 4-HO-DBT * 4-HO-EPT * 4-HO-McPT * (Lucigenol) 4-HO-MPMI * (Meprocin) 4-HO-MPT * 5-MeO-EiPT * 5-MeO-MALT * 5-MeO-MPMI * Aeruginascin * Baeocystin * DBT * DCPT * EiPT * EPT * MPT * PiPT Others| * AL-38022A * ALPHA * Dimemebfe * Efavirenz * Lorcaserin * M-ALPHA * RH-34 Also empathogens in general (e. g.: 5-APB, 5-MAPB]], 6-APB and other substituted benzofurans, Chemistry:MDAI Dissociatives (NMDAR antagonists)| | Arylcyclo‐ hexylamines| | Ketamine-related| * 2-Fluorodeschloroketamine * Arketamine ((R)-ketamine) * Deschloroketamine * Ethketamine (N-Ethylnorketamine) * Esketamine ((S)-ketamine) * Ketamine * Methoxetamine * Methoxmetamine * Methoxyketamine * Norketamine * Tiletamine | PCP-related| * 3'-HO-PCP * 3'-MeO-PCE * 3'-MeO-PCMo * 3'-MeO-PCP * BDPC * Dieticyclidine (PCDE) * Eticyclidine (PCE) * Methoxydine (4'-MeO-PCP) * PCPr * Phencyclidine (PCP) * Rolicyclidine (PCPy) * Tenocyclidine (TCP) Others| * BTCP * Gacyclidine * PRE-084 Diarylethylamines| * Diphenidine * Ephenidine * Fluorolintane * Methoxphenidine Morphinans| * Dextrallorphan * Dextromethorphan * Dextrorphan * Racemethorphan * Racemorphan Others| * 2-EMSB * 2-MDP * 8A-PDHQ * Aptiganel * Budipine * Delucemine * Dexoxadrol * Dizocilpine * Etoxadrol * Herkinorin * Ibogaine * Midafotel * NEFA * Neramexane * Nitrous oxide * Noribogaine * Perzinfotel * RB-64 * Remacemide * Salvinorin A * Selfotel * Xenon Deliriants (mAChR antagonists)| * Atropine * Benactyzine * Benzatropine * Benzydamine * Biperiden * BRN-1484501 * Brompheniramine * BZ * CAR-226,086 * CAR-301,060 * CAR-302,196 * CAR-302,282 * CAR-302,368 * CAR-302,537 * CAR-302,668 * Chloropyramine * Chlorphenamine * Clemastine * CS-27349 * Cyclizine * Cyproheptadine * Dicycloverine * Dimenhydrinate * Diphenhydramine * Ditran * Doxylamine * EA-3167 * EA-3443 * EA-3580 * EA-3834 * Elemicin * Flavoxate * Hyoscyamine * JB-318 * JB-336 * Meclozine * Mepyramine * Myristicin * Orphenadrine * Oxybutynin * Pheniramine * Phenyltoloxamine * Procyclidine * Promethazine * Scopolamine * Tolterodine * Trihexyphenidyl * Tripelennamine * Triprolidine * WIN-2299 Others| | Cannabinoids (CB1 agonists)| | Natural| * THC (Dronabinol) * THCV | Synthetic| | AM-x| * AM-087 * AM-251 * AM-279 * AM-281 * AM-356 * AM-374 * AM-381 * AM-404 * AM-411 * AM-630 * AM-661 * AM-678 * AM-679 * AM-694 * AM-735 * AM-855 * AM-881 * AM-883 * AM-905 * AM-906 * AM-919 * AM-926 * AM-938 * AM-1116 * AM-1172 * AM-1220 * AM-1221 * AM-1235 * AM-1241 * AM-1248 * AM-1710 * AM-1714 * AM-1902 * AM-2201 * AM-2212 * AM-2213 * AM-2232 * AM-2233 * AM-2389 * AM-3102 * AM-4030 * AM-4054 * AM-4056 * AM-4113 * AM-6545 | CP x| * CP 47,497 * CP 55,244 * CP 55,940 * (±)-CP 55,940 * (+)-CP 55,940 * (-)-CP 55,940 HU-x| * HU-210 * HU-211 * HU-239 * HU-243 * HU-308 * HU-320 * HU-331 * HU-336 * HU-345 JWH-x| * JWH-007 * JWH-015 * JWH-018 * JWH-019 * JWH-030 * JWH-047 * JWH-048 * JWH-051 * JWH-057 * JWH-073 * JWH-081 * JWH-098 * JWH-116 * JWH-120 * JWH-122 * JWH-133 * JWH-139 * JWH-147 * JWH-148 * JWH-149 * JWH-149 * JWH-161 * JWH-164 * JWH-166 * JWH-167 * JWH-171 * JWH-175 * JWH-176 * JWH-181 * JWH-182 * JWH-184 * JWH-185 * JWH-192 * JWH-193 * JWH-193 * JWH-194 * JWH-195 * JWH-196 * JWH-197 * JWH-198 * JWH-199 * JWH-200 * JWH-203 * JWH-205 * JWH-210 * JWH-210 * JWH-213 * JWH-220 * JWH-229 * JWH-234 * JWH-249 * JWH-250 * JWH-251 * JWH-253 * JWH-258 * JWH-300 * JWH-302 * JWH-307 * JWH-336 * JWH-350 * JWH-359 * JWH-387 * JWH-398 * JWH-424 Misc. designer cannabinoids| * 4-HTMPIPO * 5F-AB-FUPPYCA * 5F-AB-PINACA * 5F-ADB * 5F-ADB-PINACA * 5F-ADBICA * 5F-AMB * 5F-APINACA * 5F-CUMYL-PINACA * 5F-NNE1 * 5F-PB-22 * 5F-SDB-006 * A-796,260 * A-836,339 * AB-001 * AB-005 * AB-CHFUPYCA * AB-CHMINACA * AB-FUBINACA * AB-PINACA * ADAMANTYL-THPINACA * ADB-CHMINACA * ADB-FUBINACA * ADB-PINACA * ADBICA * ADSB-FUB-187 * AMB-FUBINACA * APICA * APINACA * APP-FUBINACA * CB-13 * CUMYL-PICA * CUMYL-PINACA * CUMYL-THPINACA * DMHP * EAM-2201 * FAB-144 * FDU-PB-22 * FUB-144 * FUB-APINACA * FUB-JWH-018 * FUB-PB-22 * FUBIMINA * JTE 7-31 * JTE-907 * Levonantradol * MDMB-CHMICA * MDMB-CHMINACA * MDMB-FUBINACA * MEPIRAPIM * MAM-2201 * MDA-19 * MN-18 * MN-25 * NESS-0327 * NESS-040C5 * Nabilone * Nabitan * NM-2201 * NNE1 * Org 28611 * Parahexyl * PTI-1 * PTI-2 * PX-1 * PX-2 * PX-3 * QUCHIC * QUPIC * RCS-4 * RCS-8 * SDB-005 * SDB-006 * STS-135 * THC-O-acetate * THC-O-phosphate * THJ-018 * THJ-2201 * UR-144 * WIN 55,212-2 * XLR-11 D2 agonists| * Apomorphine * Aporphine * Bromocriptine * Cabergoline * Lisuride * Memantine * Nuciferine * Pergolide * Phenethylamine * Piribedil * Pramipexole * Ropinirole * Rotigotine * Salvinorin A Also indirect D2 agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa). GABAA enhancers| * CI-966 * Eszopiclone * Ibotenic acid * Muscimol (Amanita muscaria) * Zaleplon * Zolpidem * Zopiclone Inhalants (Mixed MOA)| * Aliphatic hydrocarbons * Butane * Gasoline * Kerosene * Propane * Aromatic hydrocarbons * Toluene * Ethers * Diethyl ether * Enflurane * Haloalkanes * Chlorofluorocarbons * Chloroform κOR agonists| * 2-EMSB * Alazocine * Bremazocine * Butorphan * Butorphanol * Cyclazocine * Cyclorphan * Cyprenorphine * Diprenorphine * Enadoline * Herkinorin * Heroin * HZ-2 * Ibogaine * Ketazocine * Levallorphan * Levomethorphan * Levorphanol * LPK-26 * Metazocine * Morphine * Nalbuphine * Nalmefene * Nalorphine * Noribogaine * Oxilorphan * Pentazocine * Phenazocine * Proxorphan * Racemethorphan * Racemorphan * Salvinorin A * Spiradoline * Tifluadom * U-50488 * U-69,593 * Xorphanol Others| * Glaucine * Isoaminile * Noscapine * Pukateine Pharmacodynamics * v * t * e Adrenergic receptor modulators α1| * Agonists: 6-FNE * Amidephrine * Anisodine * Buspirone * Cirazoline * Corbadrine * Desglymidodrine * Dexisometheptene * Dipivefrine * Dopamine * Droxidopa (L-DOPS) * Ephedrine * Epinephrine * Etilefrine * Etilevodopa * Ethylnorepinephrine * Indanidine * Isometheptene * L-DOPA (levodopa) * L-Phenylalanine * L-Tyrosine * Melevodopa * Metaraminol * Methoxamine * Methyldopa * Midodrine * Naphazoline * Norepinephrine * Octopamine (drug) * Oxymetazoline * Phenylephrine * Phenylpropanolamine * Pseudoephedrine * Synephrine * Tetryzoline * Tiamenidine * XP21279 * Xylometazoline * Antagonists: Abanoquil * Adimolol * Ajmalicine * Alfuzosin * Amosulalol * Anisodamine * Arotinolol * Atiprosin * Atypical antipsychotics (e.g., brexpiprazole, clozapine,Chemistry:Olanzapine α2| * Agonists: (R)-3-Nitrobiphenyline * 4-NEMD * 6-FNE * Amitraz * Apraclonidine * Brimonidine * Cannabivarin * Clonidine * Corbadrine * Detomidine * Dexmedetomidine * Dihydroergotamine * Dipivefrine * Dopamine * Droxidopa (L-DOPS) * Etilevodopa * Ephedrine * Ergotamine * Epinephrine * Etilefrine * Ethylnorepinephrine * Guanabenz * Guanfacine * Guanoxabenz * L-DOPA (levodopa) * L-Phenylalanine * L-Tyrosine * Lofexidine * Medetomidine * Melevodopa * Methyldopa * Mivazerol * Naphazoline * Norepinephrine * Oxymetazoline * Phenylpropanolamine * Piperoxan * Pseudoephedrine * Rezatomidine * Rilmenidine * Romifidine * Talipexole * Tasipimidine * Tetrahydrozoline * Tiamenidine * Tizanidine * Tolonidine * Urapidil * Vatinoxan * XP21279 * Xylazine * Xylometazoline * Antagonists: 1-PP * Adimolol * Amesergide * Aptazapine * Atipamezole * Atypical antipsychotics (e.g., asenapine, Chemistry:Brexpiprazole * Agonists: Abediterol * Alifedrine * Amibegron * Arbutamine * Arformoterol * Arotinolol * BAAM * Bambuterol * Befunolol * Bitolterol * Broxaterol * Buphenine * Carbuterol * Carmoterol * Cimaterol * Clenbuterol * Colterol * Corbadrine * Denopamine * Dipivefrine * Dobutamine * Dopamine * Dopexamine * Droxidopa (L-DOPS) * Ephedrine * Epinephrine * Etafedrine * Etilefrine * Etilevodopa * Ethylnorepinephrine * Fenoterol * Formoterol * Hexoprenaline * Higenamine * Indacaterol * Isoetarine * Isoprenaline * Isoxsuprine * L-DOPA (levodopa) * L-Phenylalanine * L-Tyrosine * Levosalbutamol * Mabuterol * Melevodopa * Methoxyphenamine * Methyldopa * Mirabegron * Norepinephrine * Orciprenaline * Oxyfedrine * PF-610355 * Phenylpropanolamine * Pirbuterol * Prenalterol * Ractopamine * Procaterol * Pseudoephedrine * Reproterol * Rimiterol * Ritodrine * Salbutamol * Salmeterol * Solabegron * Terbutaline * Tretoquinol * Tulobuterol * Vilanterol * Xamoterol * XP21279 * Zilpaterol * Zinterol * Antagonists: Acebutolol * Adaprolol * Adimolol * Afurolol * Alprenolol * Alprenoxime * Amosulalol * Ancarolol * Arnolol * Arotinolol * Atenolol * Befunolol * Betaxolol * Bevantolol * Bisoprolol * Bopindolol * Bornaprolol * Brefonalol * Bucindolol * Bucumolol * Bufetolol * Bufuralol * Bunitrolol * Bunolol * Bupranolol * Butaxamine * Butidrine * Butofilolol * Capsinolol * Carazolol * Carpindolol * Carteolol * Carvedilol * Celiprolol * Cetamolol * Cicloprolol * Cinamolol * Cloranolol * Cyanopindolol * Dalbraminol * Dexpropranolol * Diacetolol * Dichloroisoprenaline * Dihydroalprenolol * Dilevalol * Diprafenone * Draquinolol * Ecastolol * Epanolol * Ericolol * Ersentilide * Esatenolol * Esprolol * Eugenodilol * Exaprolol * Falintolol * Flestolol * Flusoxolol * Hydroxycarteolol * Hydroxytertatolol * ICI-118,551 * Idropranolol * Indenolol * Indopanolol * Iodocyanopindolol * Iprocrolol * Isoxaprolol * Isamoltane * Labetalol * Landiolol * Levobetaxolol * Levobunolol * Levomoprolol * Medroxalol * Mepindolol * Metipranolol * Metoprolol * Moprolol * Nadolol * Nadoxolol * Nebivolol * Nifenalol * Nipradilol * Oxprenolol * Pacrinolol * Pafenolol * Pamatolol * Pargolol * Penbutolol * Pindolol * Practolol * Primidolol * Procinolol * Pronethalol * Propafenone * Propranolol * Ridazolol * Ronactolol * Soquinolol * Sotalol * Spirendolol * SR 59230A * Sulfinalol * Talinolol * Tazolol * Tertatolol * Tienoxolol * Tilisolol * Timolol * Tiprenolol * Tolamolol * Toliprolol * Xibenolol * Xipranolol * v * t * e Dopamine receptor modulators D1-like| | Agonists| * Benzazepines: 6-Br-APB * Fenoldopam * SKF-38,393 * SKF-77,434 * SKF-81,297 * SKF-82,958 * SKF-83,959 * Trepipam * Zelandopam * Ergolines: Cabergoline * CY-208,243 * Dihydroergocryptine * LEK-8829 * Lisuride * Pergolide * Terguride * Dihydrexidine derivatives: A-77636 * A-86929 * Adrogolide (ABT-431, DAS-431) * Dihydrexidine * Dinapsoline * Dinoxyline * Doxanthrine * Phenethylamines: BCO-001 * Deoxyepinephrine (N-methyldopamine, epinine) * Dopexamine * Etilevodopa * Ibopamine * L-DOPA (levodopa) * Melevodopa * L-Phenylalanine * L-Tyrosine * XP21279 * Others: A-68930 * Apomorphine * Isocorypalmine * Nuciferine * PF-6649751 * PF 6669571 * Propylnorapomorphine * Rotigotine * SKF-89,145 * SKF-89,626 * Stepholidine * Tetrahydropalmatine | Antagonists| * Typical antipsychotics: Butaclamol * Chlorpromazine * Chlorprothixene * Flupentixol (flupenthixol) (+melitracen) * Fluphenazine * Loxapine * Perphenazine (+amitriptyline) * Pifluthixol * Thioridazine * Thiothixene * Trifluoperazine (+tranylcypromine) * Zuclopenthixol * Atypical antipsychotics: Asenapine * Clorotepine * Clotiapine * Clozapine * DHA-clozapine * Fluperlapine * Iloperidone * Norclozapine * Norquetiapine * Olanzapine (++fluoxetine) * Paliperidone * Quetiapine * Risperidone * Tefludazine * Zicronapine * Ziprasidone * Zotepine * Others: Berupipam * Ecopipam * EEDQ * Metitepine (methiothepin) * Odapipam * Perlapine * SCH-23390 D2-like| | Agonists| * Adamantanes: Amantadine * Memantine * Rimantadine * Aminotetralins: 5-OH-DPAT * 7-OH-DPAT * 8-OH-PBZI * Rotigotine * UH-232 * Ergolines: Bromocriptine * Cabergoline * Dihydroergocryptine * Epicriptine * Ergocornine * Lergotrile * Lisuride * LSD * Pergolide * Terguride * Dihydrexidine derivatives: 2-OH-NPA * Ciladopa * Dihydrexidine * Dinoxyline * N,N-Propyldihydrexidine * Phenethylamines: Deoxyepinephrine (N-methyldopamine, epinine) * Dopexamine * Etilevodopa * Ibopamine * L-DOPA (levodopa) * L-Phenylalanine * L-Tyrosine * Melevodopa * XP21279 * Atypical antipsychotics: Alentemol (U-66444B) * Aripiprazole (+sertraline) * Aripiprazole lauroxil * Bifeprunox * Brexpiprazole * Brilaroxazine * Cariprazine * F-15063 * Lumateperone * Norclozapine * Others: 3-PPP * A-412997 * ABT-670 * ABT-724 * Adrafinil * Aplindore * Apomorphine * Arketamine * Armodafinil * BP-897 * Captodiame * CP-226,269 * Dizocilpine * Esketamine * Flibanserin * GSK-789,472 * Ketamine * Mesulergine * Modafinil * OSU-6162 * Pardoprunox * PD-128,907 * PD-168,077 * PF-219,061 * PF-592,379 * Phencyclidine * Piribedil * Pramipexole * Preclamol * Propylnorapomorphine * Pukateine * Quinagolide * Quinelorane * Quinpirole * RDS-127 * Ro10-5824 * Ropinirole * Roxindole * Salvinorin A * SKF-83,959 * Sumanirole * Talipexole * Umespirone * WAY-100,635 | Antagonists| * Typical antipsychotics: Acepromazine * Acetophenazine * Azaperone * Benperidol * Bromperidol * Butaclamol * Butaperazine * Chloracizine * Chlorproethazine * Chlorpromazine * Chlorprothixene * Ciclindole * Clopenthixol * Clothixamide * Clopimozide * Droperidol * Fluacizine * Fluanisone * Flucindole * Fluotracen * Flupentixol (flupenthixol) (+melitracen) * Fluphenazine * Fluprothixene * Fluspirilene * Haloperidol * Homopipramol * Lenperone * Levomepromazine (methotrimeprazine) * Levosulpiride * Loxapine * Mesoridazine * Moperone * Naranol * Nemonapride * Penfluridol * Perathiepin * Perazine * Pericyazine (periciazine) * Perphenazine (+amitriptyline) * Piflutixol (pifluthixol) * Pimozide * Pipamperone * Preclamol * Prochlorperazine * Promazine * Prothipendyl * Spiperone (spiroperidol) * Sulforidazine * Sulpiride * Sultopride * Teflutixol * Thiopropazate * Thioproperazine * Thioridazine * Thiothixene * Timiperone * Trifluoperazine (+tranylcypromine) * Triflupromazine * Trifluperidol * Zetidoline * Zuclopenthixol * Atypical antipsychotics: Amisulpride * Asenapine * BL-1020 * Blonanserin * Carpipramine * Cinuperone * Clocapramine * Clorotepine * Clotiapine (clothiapine) * Clozapine * Cyamemazine * DHA-clozapine * Dixyrazine * Elopiprazole * Flumezapine * Fluperlapine * Gevotroline * Iloperidone * Lurasidone * Mazapertine * Melperone * Molindone * Mosapramine * Ocaperidone * Olanzapine (+fluoxetine) * Paliperidone * Perospirone * Piperacetazine * Pipotiazine * Piquindone * Quetiapine * Remoxipride * Risperidone * Sertindole * Tefludazine * Tenilapine * Tiospirone * Veralipride * Zicronapine * Ziprasidone * Zotepine * Antiemetics/gastroprokinetics/sedatives: Aceprometazine * AS-8112 * Alimemazine * Alizapride * Benzquinamide * Bromopride * Clebopride * Domperidone * Eticlopride * Hydroxyzine * Itopride * Metoclopramide * Metopimazine * Promethazine * Thiethylperazine * Trimethobenzamide * Antidepressants: Amoxapine * Nefazodone * Opipramol * Propiomazine * Trimipramine * Others: 3-PPP * Alpiropride * Azapride * Buspirone * Desmethoxyfallypride * EEDQ * F-15063 * Fallypride * Fananserin * Fenfluramine * GSK-789,472 * Iodobenzamide * Isocorypalmine * L-741,626 * L-745,870 * Levofenfluramine * LEK-8829 * Metergoline * Metitepine (methiothepin) * N-Methylspiperone * Nafadotride * Nuciferine * PNU-99,194 * Pridopidine * Raclopride * Sarizotan * SB-277,011-A * Seridopidine * Sonepiprazole * Spiroxatrine * Stepholidine * SV-293 * Tetrahydropalmatine * Tiapride * UH-232 * Yohimbine * See also: Receptor/signaling modulators * Adrenergics * Serotonergics * Monoamine reuptake inhibitors * Monoamine releasing agents * Monoamine metabolism modulators * Monoamine neurotoxins * v * t * e Serotonin receptor modulators 5-HT1| | 5-HT1A| * Agonists: 8-OH-DPAT * Adatanserin * Amphetamine * Antidepressants (e.g., etoperidone, hydroxynefazodone, nefazodone, trazodone, triazoledione, vilazodone, vortioxetine) * Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, lurasidone, quetiapine, ziprasidone) * Azapirones (e.g., buspirone, eptapirone, gepirone, perospirone, tandospirone) * Bay R 1531 * Befiradol * BMY-14802 * Cannabidiol * Dimemebfe * Dopamine * Ebalzotan * Eltoprazine * Enciprazine * Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide) * F-11461 * F-12826 * F-13714 * F-14679 * F-15063 * F-15,599 * Flesinoxan * Flibanserin * Flumexadol * Hypidone * Lesopitron * LY-293284 * LY-301317 * mCPP * MKC-242 * Naluzotan * NBUMP * Osemozotan * Oxaflozane * Pardoprunox * Piclozotan * Rauwolscine * Repinotan * Roxindole * RU-24,969 * S-14,506 * S-14671 * S-15535 * Sarizotan * Serotonin (5-HT) * SSR-181507 * Sunepitron * Tryptamines (e.g., 5-CT, 5-MeO-DMT, 5-MT, bufotenin, DMT, indorenate, N-Me-5-HT, psilocin, psilocybin) * TGBA01AD * U-92,016-A * Urapidil * Vilazodone * Xaliproden * Yohimbine * Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole) * AV965 * Beta blockers (e.g., alprenolol, carteolol, cyanopindolol, iodocyanopindolol, isamoltane, oxprenolol, penbutolol, pindobind, pindolol, propranolol, tertatolol) * BMY-7,378 * CSP-2503 * Dotarizine * Ergolines (e.g., metergoline) * FCE-24379 * Flopropione * GR-46611 * Isamoltane * Lecozotan * Mefway * Metitepine (methiothepin) * MIN-117 (WF-516) * MPPF * NAN-190 * Robalzotan * S-15535 * SB-649,915 * SDZ 216-525 * Spiperone * Spiramide * Spiroxatrine * UH-301 * WAY-100135 * WAY-100635 * Xylamidine * Unknown/unsorted: Acetryptine * Carvedilol * Ergolines (e.g., ergometrine (ergonovine)) 5-HT1B| * Agonists: Anpirtoline * CGS-12066A * CP-93129 * CP-94253 * CP-122,288 * CP-135807 * Eltoprazine * Ergolines (e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) * mCPP * RU-24,969 * Serotonin (5-HT) * Triptans (e.g., avitriptan, donitriptan, eletriptan, sumatriptan, zolmitriptan) * TFMPP * Tryptamines (e.g., 5-BT, 5-CT, 5-MT, DMT) * Vortioxetine * Antagonists: AR-A000002 * Beta blockers (e.g., alprenolol, carteolol, isamoltane, oxprenolol, penbutolol, propranolol, tertatolol) * Elzasonan * Ergolines (e.g., metergoline) * GR-127935 * Isamoltane * LY-393558 * Metitepine (methiothepin) * SB-216641 * SB-224289 * SB-236057 * Yohimbine * Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride) 5-HT1D| * Agonists: CP-122,288 * CP-135807 * CP-286601 * Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, LSD, methysergide) * Chemistry:GR-46611 * L-694247 * Chemistry:L-772405 * mCPP * PNU-109291 * PNU-142633 * Serotonin (5-HT) * TGBA01AD * Triptans (e.g., almotriptan, avitriptan, donitriptan, [[Chemistry:Eleeletriptan, Frovatriptan|frovatriptan]], naratriptan, rizatriptan, sumatriptan, zolmitriptan) * Tryptamines (e.g., 5-BT, 5-CT, 5-Et-DMT, 5-MT, 5-(nonyloxy)tryptamine, DMT) * Antagonists: Alniditan * BRL-15,572 * Elzasonan * Ergolines (e.g., metergoline) * GR-127935 * Ketanserin * LY-310762 * LY-367642 * LY-393558 * LY-456219 * LY-456220 * Metitepine (methiothepin) * Mianserin * Ritanserin * Yohimbine * Ziprasidone * Unknown/unsorted: Acetryptine * Ergolines (e.g., lisuride, lysergol, pergolide) 5-HT1E| * Agonists: BRL-54443 * Ergolines (e.g., methysergide) * Serotonin (5-HT) * Triptans (e.g., eletriptan) * Tryptamines (e.g., tryptamine) * Antagonists: Metitepine (methiothepin) * Unknown/unsorted: ErgIrindaloneolines (e.g., ergometrine (ergonovine), lysergol, methylergometrine (methylergonovine) 5-HT1F| * Agonists: BRL-54443 * CP-122,288 * Ergolines (e.g., bromocriptine, lysergol, methylergometrine (methylergonovine) methysergide) * Lasmiditan * LY-334370 * Serotonin (5-HT) * Triptans (e.g., eletriptan, naratriptan, sumatriptan) * Tryptamines (e.g., 5-MT) * Antagonists: Metitepine (methiothepin) * Mianserin 5-HT2| | 5-HT2A| * Agonists: 25H/NB series (e.g., 25I-NBF, 25I-NBMD, 25I-NBOH, 25I-NBOMe, 25B-NBOMe, 25C-NBOMe, 25TFM-NBOMe, 2CBCB-NBOMe, 25CN-NBOH, 2CBFly-NBOMe) * 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21) * 2C-B-FLY * 2CB-Ind * 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT) * α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT) * AL-34662 * AL-37350A * Bromo-DragonFLY * Dimemebfe * DMBMPP * DOx (e.g., DOB, DOC, DOI, DOM) * Efavirenz * Ergolines (e.g., 1P-LSD, ALD-52, bromocriptine, cabergoline, ergine (LSA), ergometrine (ergonovine), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, methylergometrine (methylergonovine), pergolide) * Flumexadol * IHCH-7113 * Jimscaline * Lorcaserin * MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA) * O-4310 * Oxaflozane * PHA-57378 * PNU-22394 * PNU-181731 * RH-34 * SCHEMBL5334361 * Phenethylamines (e.g., lophophine, mescaline) * Piperazines (e.g., BZP, quipazine, TFMPP) * Serotonin (5-HT) * TCB-2 * TFMFly * Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) * Antagonists: 5-I-R91150 * 5-MeO-NBpBrT * AC-90179 * Adatanserin * Altanserin * Antihistamines (e.g., cyproheptadine, hydroxyzine, ketotifen, perlapine) * AMDA * Atypical antipsychotics (e.g., amperozide, aripiprazole, asenapine, blonanserin, brexpiprazole, carpipramine, clocapramine, clorotepine, clozapine, fluperlapine, gevotroline, iloperidone, lurasidone, melperone, mosapramine, ocaperidone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zicronapine, ziprasidone, zotepine) * Chlorprothixene * Cinanserin * CSP-2503 * Deramciclane * Dotarizine * Eplivanserin * Ergolines (e.g., amesergide, LY-53857, LY-215,840, mesulergine, metergoline, methysergide, sergolexole) * Fananserin * Flibanserin * Glemanserin * Irindalone * Ketanserin * KML-010 * Landipirdine * LY-393558 * mCPP * Medifoxamine * Metitepine (methiothepin) * MIN-117 (WF-516) * Naftidrofuryl * Nantenine * Nelotanserin * Opiranserin (VVZ-149) * Pelanserin * Phenoxybenzamine * Pimavanserin * Pirenperone * Pizotifen * Pruvanserin * Rauwolscine * Ritanserin * Roluperidone * S-14671 * Sarpogrelate * Serotonin antagonists and reuptake inhibitors (e.g., etoperidone, hydroxynefazodone, lubazodone, mepiprazole, nefazodone, triazoledione, trazodone) * SR-46349B * TGBA01AD * Teniloxazine * Temanogrel * Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) * Tricyclic antidepressants (e.g., amitriptyline) * Typical antipsychotics (e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone, prochlorperazine, setoperone, spiperone, spiramide, thioridazine, thiothixene, trifluoperazine) * Volinanserin * Xylamidine * Yohimbine * Unknown/unsorted: Ergolines (e.g., dihydroergotamine, nicergoline) 5-HT2B| * Agonists: 4-Methylaminorex * Aminorex * Amphetamines (e.g., chlorphentermine, cloforex, dexfenfluramine, fenfluramine, levofenfluramine, norfenfluramine) * BW-723C86 * DOx (e.g., DOB, DOC, DOI, DOM) * Ergolines (e.g., cabergoline, dihydroergocryptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) * Lorcaserin * MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA) * Piperazines (e.g., TFMPP) * PNU-22394 * Ro60-0175 * Serotonin (5-HT) * Tryptamines (e.g., 5-BT, 5-CT, 5-MT, α-Me-5-HT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) * Antagonists: Agomelatine * Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, N-desalkylquetiapine (norquetiapine), N-desmethylclozapine (norclozapine), olanzapine, pipamperone, quetiapine, risperidone, ziprasidone) * Cyproheptadine * EGIS-7625 * Ergolines (e.g., amesergide, bromocriptine, lisuride, LY-53857, LY-272015, mesulergine) * Ketanserin * LY-393558 * mCPP * Metadoxine * Metitepine (methiothepin) * Pirenperone * Pizotifen * Propranolol * PRX-08066 * Rauwolscine * Ritanserin * RS-127445 * Sarpogrelate * SB-200646 * SB-204741 * SB-206553 * SB-215505 * SB-221284 * SB-228357 * SDZ SER-082 * Tegaserod * Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine) * Trazodone * Typical antipsychotics (e.g., chlorpromazine) * TIK-301 * Yohimbine * Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine)) 5-HT2C| * Agonists: 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21) * 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT) * α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT) * A-372159 * AL-38022A * Alstonine * CP-809101 * Dimemebfe * DOx (e.g., DOB, DOC, DOI, DOM) * Ergolines (e.g., ALD-52, cabergoline, dihydroergotamine, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, pergolide) * Flumexadol * Lorcaserin * MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA) * MK-212 * ORG-12962 * ORG-37684 * Oxaflozane * PHA-57378 * Phenethylamines (e.g., lophophine, mescaline) * Piperazines (e.g., aripiprazole, BZP, mCPP, quipazine, TFMPP) * PNU-22394 * PNU-181731 * Ro60-0175 * Ro60-0213 * Serotonin (5-HT) * Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) * Vabicaserin * WAY-629 * WAY-161503 * YM-348 * Antagonists: Adatanserin * Agomelatine * Atypical antipsychotics (e.g., asenapine, clorotepine, clozapine, fluperlapine, iloperidone, melperone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, ziprasidone, zotepine) * Captodiame * CEPC * Cinanserin * Cyproheptadine * Deramciclane * Desmetramadol * Dotarizine * Eltoprazine * Ergolines (e.g., amesergide, bromocriptine, LY-53857, LY-215,840, mesulergine, metergoline, methysergide, sergolexole) * Etoperidone * Fluoxetine * FR-260010 * Irindalone * Ketanserin * Ketotifen * Latrepirdine (dimebolin) * Medifoxamine * Metitepine (methiothepin) * Nefazodone * Pirenperone * Pizotifen * Propranolol * Ritanserin * RS-102221 * S-14671 * SB-200646 * SB-206553 * SB-221284 * SB-228357 * SB-242084 * SB-243213 * SDZ SER-082 * Tedatioxetine * Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) * TIK-301 * Tramadol * Trazodone * Tricyclic antidepressants (e.g., amitriptyline, nortriptyline) * Typical antipsychotics (e.g., chlorpromazine, loxapine, pimozide, pipamperone, thioridazine) * Xylamidine * Unknown/unsorted: Efavirenz * Ergolines (e.g., ergometrine (ergonovine), methylergometrine (methylergonovine)) 5-HT3–7| | 5-HT3| * Agonists: Alcohols (e.g., butanol, ethanol (alcohol), trichloroethanol) * m-CPBG * Phenylbiguanide * Piperazines (e.g., BZP, mCPP, quipazine) * RS-56812 * Serotonin (5-HT) * SR-57227 * SR-57227A * Tryptamines (e.g., 2-Me-5-HT, 5-CT, bufotenidine (5-HTQ)) * Volatiles/gases (e.g., halothane, isoflurane, toluene, trichloroethane) * YM-31636 * Antagonists: Alosetron * Chemistry:Arazasetron * AS-8112 * Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine) * Azasetron * Batanopride * Bemesetron (MDL-72222) * Bupropion * Cilansetron * CSP-2503 * Dazopride * Dolasetron * Galanolactone * Granisetron * Hydroxybupropion * Lerisetron * Memantine * Ondansetron * Palonosetron * Ramosetron * Renzapride * Ricasetron * Tedatioxetine * Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine) * Thujone * Tropanserin * Tropisetron * Typical antipsychotics (e.g., loxapine) * Volatiles/gases (e.g., nitrous oxide, sevoflurane, xenon) * Vortioxetine * Zacopride * Zatosetron * Unknown/unsorted: LY-53857 * Piperazines (e.g., naphthylpiperazine) 5-HT4| * Agonists: 5-MT * BIMU8 * Capeserod * Cinitapride * Cisapride * CJ-033466 * Dazopride * Metoclopramide * Minesapride * Mosapride * Prucalopride * PRX-03140 * Renzapride * RS-67,333 * RS-67,506 * Serotonin (5-HT) * Tegaserod * Usmarapride * Velusetrag * Zacopride * Antagonists: GR-113808 * GR-125487 * L-Lysine * Piboserod * RS-39604 * RS-67532 * SB-203186 * SB-204070 5-HT5A| * Agonists: Ergolines (e.g., 2-Br-LSD (BOL-148), ergotamine, LSD) * Serotonin (5-HT) * Tryptamines (e.g., 5-CT) * Valerenic acid * Antagonists: Asenapine * Latrepirdine (dimebolin) * Metitepine (methiothepin) * Ritanserin * SB-699551 * Unknown/unsorted: Ergolines (e.g., metergoline, methysergide) * Piperazines (e.g., naphthylpiperazine) 5-HT6| * Agonists: Ergolines (e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide) * Hypidone * Serotonin (5-HT) * Tryptamines (e.g., 2-Me-5-HT, 5-BT, 5-CT, 5-MT, Bufotenin, E-6801, E-6837, EMD-386088, EMDT, LY-586713, N-Me-5-HT, ST-1936, tryptamine) * WAY-181187 * WAY-208466 * Antagonists: ABT-354 * Atypical antipsychotics (e.g., aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, iloperidone, olanzapine, tiospirone) * AVN-101 * AVN-211 * AVN-322 * AVN-397 * BGC20-760 * BVT-5182 * BVT-74316 * Cerlapirdine * EGIS-12,233 * GW-742457 * Idalopirdine * Ketanserin * Landipirdine * Latrepirdine (dimebolin) * Masupirdine * Metitepine (methiothepin) * MS-245 * PRX-07034 * Ritanserin * Ro 04-6790 * Ro 63-0563 * SB-258585 * SB-271046 * SB-357134 * SB-399885 * SB-742457 * Tetracyclic antidepressants (e.g., amoxapine, mianserin) * Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, nortriptyline) * Typical antipsychotics (e.g., chlorpromazine, loxapine) * Unknown/unsorted: Ergolines (e.g., 2-Br-LSD (BOL-148), bromocriptine, lergotrile, pergolide) * Piperazines (e.g., naphthylpiperazine) 5-HT7| * Agonists: 8-OH-DPAT * AS-19 * Bifeprunox * E-55888 * Ergolines (e.g., LSD) * LP-12 * LP-44 * LP-211 * RU-24,969 * Sarizotan * Serotonin (5-HT) * Triptans (e.g., frovatriptan) * Tryptamines (e.g., 5-CT, 5-MT, bufotenin, N-Me-5-HT) * Antagonists: Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, clorotepine, clozapine, fluperlapine, olanzapine, risperidone, sertindole, tiospirone, ziprasidone, zotepine) * Butaclamol * DR-4485 * EGIS-12,233 * Ergolines (e.g., 2-Br-LSD (BOL-148), amesergide, bromocriptine, cabergoline, dihydroergotamine, ergotamine, LY-53857, LY-215,840, mesulergine, metergoline, methysergide, sergolexole) * JNJ-18038683 * Ketanserin * LY-215,840 * Metitepine (methiothepin) * Ritanserin * SB-258719 * SB-258741 * SB-269970 * SB-656104 * SB-656104A * SB-691673 * SLV-313 * SLV-314 * Spiperone * Chemistry:SSR-181507 * Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine) * Tricyclic antidepressants (e.g., amitriptyline, clomipramine, imipramine) * Typical antipsychotics (e.g., acetophenazine, chlorpromazine, chlorprothixene, fluphenazine, loxapine, pimozide) * Vortioxetine * Unknown/unsorted: Ergolines (e.g., lisuride, pergolide) * Piperazines (e.g., naphthylpiperazine) * See also: Receptor/signaling modulators * Adrenergics * Dopaminergics * Melatonergics * Monoamine reuptake inhibitors and releasing agents * Monoamine metabolism modulators * Monoamine neurotoxins * 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) 0.00 (0 votes) Original source: https://en.wikipedia.org/wiki/Methylergometrine. Read more | Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Methylergometrine&oldid=2598355" *[CID]: Compound ID *[v]: View this template *[t]: Discuss this template *[e]: Edit this template *[NB3OMe]: NB: N-benzyl; 3OMe: 3-methoxy *[NB4OMe]: NB: N-benzyl; 4OMe: 4-methoxy *[NBF]: NB: N-benzyl; F: fluoro *[NBMD]: NB: N-benzyl; MD: methylenedioxy *[NBOH]: NB: N-benzyl; OH: hydroxy *[NBOMe]: NB: N-benzyl; OMe: methoxy *[DALT]: N,N-Diallyltryptamine *[DET]: N,N-Diethyltryptamine *[DiPT]: N,N-Diisopropyltryptamine *[DMT]: N,N-Dimethyltryptamine *[DPT]: N,N-Dipropyltryptamine *[MET]: N-Methyl-N-ethyltryptamine *[MiPT]: N-Methyl-N-isopropyltryptamine