Methylergometrine

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Methylergometrine

Systematic (IUPAC) name
9,10-didehydro- N-[1-(hydroxymethyl)- propyl]- D-lysergamide
Identifiers
CAS number	113-42-8
ATC code	G02AB01
PubChem	CID 8226
Synonyms	Methylergobasine Methylergobrevin Methylergonovine
Chemical data
Formula	C₂₀H₂₅N₃O₂
Mol. mass	339.432 g/mol
SMILES	eMolecules & PubChem
Physical data
Melt. point	172 °C (342 °F)
Solubility in water	insoluble mg/mL (20 °C)
Pharmacokinetic data
Metabolism	liver
Half-life	30-120 min
Therapeutic considerations
Pregnancy cat.	C(US)
Legal status	℞ Prescription only
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Methylergometrine (other names include methylergonovine, methylergobasin, methergine, and d-lysergic acid 1-butanol amide) is a synthetic analogue of ergonovine, a psychedelic alkaloid found in ergot, and many species of morning glory. It is a member of the ergoline family and chemically similar to LSD, ergine, ergometrine, and lysergic acid. Due to its oxytocic properties, it has a medical use in obstetrics. According to Jonathan Ott, methylergonovine has LSD-like actions above 2 milligrams^{[citation needed]}. Clinical dosages are ten times lower.

Methylergometrine maleate is marketed under the trade name Methergine.

[edit] Obstetric use

Methylergometrine is a blood vessel constrictor and smooth muscle agonist most commonly used to prevent or control excessive bleeding following childbirth and spontaneous or elective abortion. It also causes uterine contractions 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.

[edit] Side effects

Cholinergic effects such as nausea, vomiting, and diarrhea
Cramping
Dizziness
Pulmonary hypertension
Coronary artery vasoconstriction
Severe systemic hypertension (especially in patients with preeclampsia)

[edit] Contraindications

Hypertension
Pregnancy

Uterotonics/labor inducers/oxytocics (G02A)

Cervical ripening

Ergot alkaloids	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 • WAY-267,464

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: OBS

phys/devp

mthr/fetu/infc, epon

proc, drug(2A/G2C)

Hallucinogens

Psychedelics
5-HT_2AR agonists

Lysergamides: AL-LAD • ALD-52 • BU-LAD • CYP-LAD • DAM-57 • Diallyllysergamide • Ergometrine (Ergonovine, Ergobasine) • ETH-LAD • LAE-32 • LSA (Ergine, Lysergamide) • LSD • LSH • LPD-824 • LSM-775 • Lysergic Acid 2-Butyl Amide • Lysergic Acid 2,4-Dimethylazetidide • Lysergic Acid 3-Pentyl Amide • Methylergometrine • Methylisopropyllysergamide • Methysergide • MLD-41 • PARGY-LAD • PRO-LAD;
Phenethylamines: Aleph • 2C-B • 2C-B-FLY • 2CBFly-NBOMe • 2C-C • 2C-C-NBOMe • 2C-CN-NBOMe • 2C-D • 2CD-5EtO • 2C-D-NBOMe • 2C-E • 2C-EF • 2C-E-NBOMe • 2C-F • 2C-F-NBOMe • 2C-G • 2C-G-NBOMe • 2C-H-NBOMe • 2C-I • 2C-N • 2C-N-NBOMe • 2C-O • 2C-O-4 • 2C-P • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-4-NBOMe • 2C-T-7 • 2C-T-7-NBOH • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-TFM-NBOMe • 2C-YN • 2CBCB-NBOMe • 25B-NBOMe • 25I-NBMD • 25I-NBOH • 25I-NBOMe • 3C-E • 3C-P • 5-APB • 5-APDB • 6-APB • 6-APDB • Br-DFLY • DESOXY • DMMDA • DMMDA-2 • DOB • DOC • DOEF • DOET • DOF • DOI • DOM • DON • DOPR • DOTFM • Escaline • Ganesha • HOT-2 • HOT-7 • HOT-17 • IAP • Isoproscaline • Jimscaline • Lophophine • MDA • MDEA • MDMA • MMA • MMDA • MMDA-2 • MMDA-3a • MMDMA • Macromerine • Mescaline • Methallylescaline • NBOMe-mescaline • Proscaline • TCB-2 • TFMFly • TMA;
Piperazines: pFPP • TMFPP;
Tryptamines: 1-Methyl-5-methoxy-diisopropyltryptamine • 2,N,N-TMT • 4,N,N-TMT • 4-HO-5-MeO-DMT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-Acetoxy-DPT • 4-Acetoxy-MiPT • 4-HO-DPT • 4-HO-MET • 4-Propionyloxy-DMT • 4-HO-MPMI • 5-Me-MIPT • 5-N,N-TMT • 5-AcO-DMT • 5-MeO-2,N,N-TMT • 5-MeO-4,N,N-TMT • 5-MeO-α,N,N-TMT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-EiPT • 5-MeO-MET • 5-MeO-MIPT • 5-MeO-MPMI • 7,N,N-TMT • α,N,N-TMT • α-ET • α-MT • AL-37350A • Baeocystin • Bufotenin • DALT • DBT • DCPT • DET • DIPT • DMT • DPT • EiPT • Ethocin • Ethocybin • Iprocin • MET • Miprocin • MIPT • Norbaeocystin • PiPT • Psilocin • Psilocybin;
Others: AL-38022A • Ibogaine • Noribogaine • Voacangine

Dissociatives
NMDAR antagonists

Adamantanes: Amantadine • Memantine • Rimantadine;
Arylcyclohexylamines: 3-MeO-PCP • 4-MeO-PCP • Dieticyclidine • Esketamine • Eticyclidine • Gacyclidine • Ketamine • Methoxetamine • Neramexane • Phencyclidine • PCPr • Rolicyclidine • Tenocyclidine • Tiletamine;
Morphinans: Dextrallorphan • Dextromethorphan • Dextrorphan • Methorphan (Racemethorphan) • Morphan (Racemorphan);
Others: 2-MDP • 8A-PDHQ • Aptiganel • Dexoxadrol • Dizocilpine (MK-801) • Etoxadrol • Ibogaine • Midafotel • NEFA • Nitrous Oxide • Noribogaine • Perzinfotel • Remacemide • Selfotel • Xenon

Deliriants
mAChR antagonists

3-Quinuclidinyl benzilate • Atropine • Benactyzine • Benzatropine • Benzydamine • Biperiden • Brompheniramine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • Chlorpheniramine • Chloropyramine • Clemastine • CS-27349 • Cyclizine • Cyproheptadine • Dicyclomine (Dicycloverine) • Dimenhydrinate • Diphenhydramine • Ditran • Doxylamine • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Flavoxate • Hydroxyzine • Hyoscyamine • Meclizine • Myristicin • N-Ethyl-3-piperidyl benzilate • N-Methyl-3-piperidyl benzilate • Pyrilamine • Orphenadrine • Oxybutynin • Pheniramine • Phenyltoloxamine • Procyclidine • Promethazine • Scopolamine (Hyoscine) • Tolterodine • Trihexyphenidyl • Tripelennamine • Triprolidine • WIN-2299

Miscellaneous

Cannabinoids CB₁R agonists	Cannabinol • CP-47,497 • CP-55,244 • CP-55,940 • DMHP • HU-210 • JWH-018 • JWH-030 • JWH-073 • JWH-081 • JWH-200 • JWH-250 • Nabilone • Nabitan • Nantradol • Parahexyl • THC (Dronabinol) • WIN-55,212-2

D₂R agonists	Apomorphine • Bromocriptine • Cabergoline • Lisuride • Memantine • Pergolide • Piribedil • Pramipexole • Ropinirole • Rotigotine * Also indirect D₂ agonists such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABA_AR agonists	Eszopiclone • Gaboxadol • Ibotenic Acid • Muscimol • Zolpidem • Zopiclone

Inhalants Mixed MOA	Butane • Chloroform • Diethyl Ether (Ether) • Enflurane • Freon • Gasoline (Petrol) • Kerosene (Paraffin) • Propane

κOR agonists	2-EMSB • 2-MMSB • Alazocine • Bremazocine • Butorphanol • Cyclazocine • Cyprenorphine • Dextrallorphan • Dezocine • Enadoline • Herkinorin • HZ-2 • Ibogaine • Ketazocine • Metazocine • Nalbuphine • Nalorphine • Noribogaine • Pentazocine • Phenazocine • Salvinorin A • Spiradoline • Tifluadom • U-50,488 • U-69,593

σR agonists	Dextrallorphan • Dextromethorphan • Dextrorphan • Noscapine (Narcotine)

Others	Efavirenz • Glaucine • Isoaminile