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MedKoo Cat#: 597490 | Name: Ergometrine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ergometrine is an ergot alkaloid with uterine and vascular smooth muscle contractile properties.

Chemical Structure

Ergometrine
Ergometrine
CAS#60-79-7

Theoretical Analysis

MedKoo Cat#: 597490

Name: Ergometrine

CAS#: 60-79-7

Chemical Formula: C19H23N3O2

Exact Mass: 325.1790

Molecular Weight: 325.41

Elemental Analysis: C, 70.13; H, 7.12; N, 12.91; O, 9.83

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
60-79-7
Synonym
Ergometrine; Ergobasine; Secacornin; Neofemergen;
IUPAC/Chemical Name
(6aR,9R)-N-((S)-1-hydroxypropan-2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
InChi Key
WVVSZNPYNCNODU-XTQGRXLLSA-N
InChi Code
InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1
SMILES Code
[H][C@@]1(N(C)C[C@H](C(N[C@@H](C)CO)=O)C=C12)CC3=CNC4=C3C2=CC=C4
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 325.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Ezeama CO, Eleje GU, Ezeama NN, Igwegbe AO, Ikechebelu JI, Ugboaja JO, Ezebialu IU, Eke AC. A comparison of prophylactic intramuscular ergometrine and oxytocin for women in the third stage of labor. Int J Gynaecol Obstet. 2014 Jan;124(1):67-71. doi: 10.1016/j.ijgo.2013.07.020. Epub 2013 Oct 5. PubMed PMID: 24365208. 2: Mahmud G, Javaid K, Tasnim N, Tabassum A, Bangash KT. Where does ergometrine stand in prevention of postpartum haemorrhage in caesarean section? J Pak Med Assoc. 2014 Aug;64(8):911-4. PubMed PMID: 25252517. 3: Merkel S, Köppen R, Koch M, Emmerling F, Nehls I. Lumi-ergometrine--structural identification and occurrence in sclerotia. Mycotoxin Res. 2012 Feb;28(1):59-66. doi: 10.1007/s12550-011-0116-5. Epub 2011 Nov 18. PubMed PMID: 23605983. 4: Ramzy J, New G, Cheong A, Roberts L, Teh AW. Iatrogenic anterior myocardial infarction secondary to ergometrine-induced coronary artery spasm during dilation and curettage for an incomplete miscarriage. Int J Cardiol. 2015 Nov 1;198:154-6. doi: 10.1016/j.ijcard.2015.06.106. Epub 2015 Jul 3. PubMed PMID: 26163906. 5: Tan J, Cao Q, He GL, Cai YH, Yu JJ, Sun X, Li YP. Misoprostol versus ergometrine-oxytocin for preventing postpartum haemorrhage: a systematic review and meta-analysis of randomized controlled trials. J Evid Based Med. 2016 Nov;9(4):194-204. doi: 10.1111/jebm.12201. Review. PubMed PMID: 27187008. 6: Johnston D, Hughes D. Bronchospasm following ergometrine in a non-asthmatic patient. Int J Obstet Anesth. 2013 Jul;22(3):261-2. doi: 10.1016/j.ijoa.2013.03.004. Epub 2013 May 3. PubMed PMID: 23648057. 7: Hu Y, Zhang Z, Li G. A novel chemiluminescence method for the determination of ergometrine maleate in serum sample without chemiluminescence reagent. Talanta. 2010 Apr 15;81(1-2):499-504. doi: 10.1016/j.talanta.2009.12.032. Epub 2009 Dec 29. PubMed PMID: 20188953. 8: Karatza AA, Tzavara M, Filias A, Krokidas G, Dimitriou G. Response to the article: Late onset of coronary vasospasm after administration of methyl-ergometrine for gynecologic bleeding [Santoro F, Spennati G, Ieva R, De Gennaro L, Correale M, Lopizzo A, Di Biase M, Brunetti ND. Int J Cardiol 2012; 161: e29-e30]. Int J Cardiol. 2013 Oct 15;168(6):5467-8. doi: 10.1016/j.ijcard.2013.07.244. Epub 2013 Aug 2. PubMed PMID: 23972960. 9: de Groot AN, Hekster YA, Vree TB, van Dongen PW. Ergometrine and methylergometrine tablets are not stable under simulated tropical conditions. J Clin Pharm Ther. 1995 Apr;20(2):109-13. PubMed PMID: 7650071. 10: de Groot AN, van Roosmalen J, van Dongen PW, Borm GF. A placebo-controlled trial of oral ergometrine to reduce postpartum hemorrhage. Acta Obstet Gynecol Scand. 1996 May;75(5):464-8. PubMed PMID: 8677772. 11: Lv Y, Zhang Z, Gong Z, Hu Y, He D. Determination and pharmacokinetics of ergometrine maleate in rabbit blood with on line microdialysis sampling and fluorescence detection. J Pharm Biomed Anal. 2005 Jun 1;38(1):29-33. PubMed PMID: 15907615. 12: Hogerzeil HV, Walker GJ. Instability of (methyl)ergometrine in tropical climates: an overview. Eur J Obstet Gynecol Reprod Biol. 1996 Oct;69(1):25-9. Review. PubMed PMID: 8909953. 13: Balki M, Dhumne S, Kasodekar S, Kingdom J, Windrim R, Carvalho JC. Oxytocin-ergometrine co-administration does not reduce blood loss at caesarean delivery for labour arrest. BJOG. 2008 Apr;115(5):579-84. doi: 10.1111/j.1471-0528.2007.01658.x. PubMed PMID: 18333937. 14: Brazenor RM, Angus JA. Ergometrine contracts isolated canine coronary arteries by a serotonergic mechanism: no role for alpha adrenoceptors. J Pharmacol Exp Ther. 1981 Aug;218(2):530-6. PubMed PMID: 6114172. 15: Balsara JJ, Bapat TR, Nandal NV, Gada VP, Chandorkar AG. Head-twitch response induced by ergometrine in mice: behavioural evidence for direct stimulation of central 5-hydroxytryptamine receptors by ergometrine. Psychopharmacology (Berl). 1986;88(3):275-8. PubMed PMID: 2938207. 16: Pijnenburg AJ, Honig WM, Boudier HA, Cools AR, Van der Heyden JA, Van Rossum JM. Further investigations on the effects of ergometrine and other ergot derivatives following injection into the nucleus accumbens of the rat. Arch Int Pharmacodyn Ther. 1976 Jul;222(1):103-15. PubMed PMID: 984962. 17: Dargaville PA, Campbell NT. Overdose of ergometrine in the newborn infant: acute symptomatology and long-term outcome. J Paediatr Child Health. 1998 Feb;34(1):83-9. PubMed PMID: 9568949. 18: Mitchell GG, Elbourne DR. The Salford Third Stage Trial. Oxytocin plus ergometrine versus oxytocin alone in the active management of the third stage of labor. Online J Curr Clin Trials. 1993 Aug 13;Doc No 83:[2305 words; 32 paragraphs]. Review. PubMed PMID: 8306013. 19: Shymanovich T, Saari S, Lovin ME, Jarmusch AK, Jarmusch SA, Musso AM, Charlton ND, Young CA, Cech NB, Faeth SH. Alkaloid variation among epichloid endophytes of sleepygrass (Achnatherum robustum) and consequences for resistance to insect herbivores. J Chem Ecol. 2015 Jan;41(1):93-104. doi: 10.1007/s10886-014-0534-x. Epub 2014 Dec 11. PubMed PMID: 25501262. 20: Aramide TM, Olusegun AK, Akinfolarin AC, Oriola DF. Oral misoprostol in the prevention of uterine bleeding after surgical evacuation of first trimester abortion: a comparative study of three uterotonic agents. Niger J Clin Pract. 2014 Jan-Feb;17(1):10-3. doi: 10.4103/1119-3077.122823. PubMed PMID: 24326799.