MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 591491 | Name: Metergoline
Featured

Description:

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

Metergoline is a psychoactive drug of the ergoline chemical class which acts as a ligand for various serotonin and dopamine receptors. A dopamine agonist and serotonin antagonist. It has been used similarly to BROMOCRIPTINE as a dopamine agonist and also for MIGRAINE DISORDERS therapy.

Chemical Structure

Metergoline
CAS#17692-51-2

Theoretical Analysis

MedKoo Cat#: 591491

Name: Metergoline

CAS#: 17692-51-2

Chemical Formula: C25H29N3O2

Exact Mass: 403.2260

Molecular Weight: 403.53

Elemental Analysis: C, 74.41; H, 7.24; N, 10.41; O, 7.93

Price and Availability

Size Price Availability Quantity
500mg USD 385.00 2 weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Metergoline;
IUPAC/Chemical Name
Carbamic acid, (((8-beta)-1,6-dimethylergolin-8-yl)methyl)-, benzyl ester
InChi Key
WZHJKEUHNJHDLS-QTGUNEKASA-N
InChi Code
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
SMILES Code
O=C(OCC1=CC=CC=C1)NC[C@H](C[C@@]23[H])CN(C)[C@]2([H])CC4=CN(C)C5=C4C3=CC=C5
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
>2 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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Metergoline is a serotonin (5-HT) receptor and dopamine receptors antagonist, with pKis of 8.64, 8.75 and 8.75 for 5-HT2A, 5-HT2B and 5-HT2C, respectively.
In vitro activity:
Both metergoline and lidocaine reversibly and concentration-dependently inhibited the peak of Na(+) currents with IC50 values of 3.6 ± 4.2 and 916.9 ± 98.8 μmol/L, respectively. Metergoline (3 μmol/L) caused a 6.8 ± 1.2 mV depolarizing shift of the steady-state activation curve of the Na(+) currents, and did not alter the inactivation curve. Reference: Acta Pharmacol Sin. 2014 Jul;35(7):862-8. https://pubmed.ncbi.nlm.nih.gov/24909513/
In vivo activity:
The behavioural response to intrathecal serotonin (5-HT) was examined in mice after acute and after withdrawal of repeated treatment with the 5-HT uptake inhibitor zimelidine or the 5-HT receptor antagonist metergoline. Acute injection of zimelidine (20 mg/kg) significantly increased the response to intrathecal 5-HT (0.25-1 micrograms) whereas a single dose of metergoline (5 mg/kg) completely blocked the response to intrathecal 5-HT (2 micrograms). Reference: Pharmacol Toxicol. 1991 Nov;69(5):361-4. https://pubmed.ncbi.nlm.nih.gov/1839446/
Solvent mg/mL mM comments
Solubility
DMF 30.0 74.34
DMF:PBS (pH 7.2) (1:2) 0.3 0.74
DMSO 63.5 157.24
Ethanol 5.0 12.39
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 403.53 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
Formulation protocol:
1. Lee JH, Liu J, Shin M, Hong M, Nah SY, Bae H. Metergoline inhibits the neuronal Nav1.2 voltage-dependent Na(+) channels expressed in Xenopus oocytes. Acta Pharmacol Sin. 2014 Jul;35(7):862-8. doi: 10.1038/aps.2014.30. Epub 2014 Jun 9. PMID: 24909513; PMCID: PMC4088281. 2. Miller KJ, King A, Demchyshyn L, Niznik H, Teitler M. Agonist activity of sumatriptan and metergoline at the human 5-HT1D beta receptor: further evidence for a role of the 5-HT1D receptor in the action of sumatriptan. Eur J Pharmacol. 1992 Sep 1;227(1):99-102. doi: 10.1016/0922-4106(92)90149-p. PMID: 1330643. 3. Currie PJ, Coscina DV. Metergoline potentiates natural feeding and antagonizes the anorectic action of medical hypothalamic 5-hydroxytryptamine. Pharmacol Biochem Behav. 1996 Apr;53(4):1023-8. doi: 10.1016/0091-3057(95)02097-7. PMID: 8801574. 4. Eide PK, Joly NM, Lund A. The behavioural response to intrathecal serotonin is changed by acute but not by repeated treatment with zimelidine or metergoline. Pharmacol Toxicol. 1991 Nov;69(5):361-4. doi: 10.1111/j.1600-0773.1991.tb01311.x. PMID: 1839446.
In vitro protocol:
1. Lee JH, Liu J, Shin M, Hong M, Nah SY, Bae H. Metergoline inhibits the neuronal Nav1.2 voltage-dependent Na(+) channels expressed in Xenopus oocytes. Acta Pharmacol Sin. 2014 Jul;35(7):862-8. doi: 10.1038/aps.2014.30. Epub 2014 Jun 9. PMID: 24909513; PMCID: PMC4088281. 2. Miller KJ, King A, Demchyshyn L, Niznik H, Teitler M. Agonist activity of sumatriptan and metergoline at the human 5-HT1D beta receptor: further evidence for a role of the 5-HT1D receptor in the action of sumatriptan. Eur J Pharmacol. 1992 Sep 1;227(1):99-102. doi: 10.1016/0922-4106(92)90149-p. PMID: 1330643.
In vivo protocol:
1. Currie PJ, Coscina DV. Metergoline potentiates natural feeding and antagonizes the anorectic action of medical hypothalamic 5-hydroxytryptamine. Pharmacol Biochem Behav. 1996 Apr;53(4):1023-8. doi: 10.1016/0091-3057(95)02097-7. PMID: 8801574. 2. Eide PK, Joly NM, Lund A. The behavioural response to intrathecal serotonin is changed by acute but not by repeated treatment with zimelidine or metergoline. Pharmacol Toxicol. 1991 Nov;69(5):361-4. doi: 10.1111/j.1600-0773.1991.tb01311.x. PMID: 1839446.
1: De Middeleer G, Dubruel P, De Saeger S. Molecularly imprinted polymers immobilized on 3D printed scaffolds as novel solid phase extraction sorbent for metergoline. Anal Chim Acta. 2017 Sep 15;986:57-70. doi: 10.1016/j.aca.2017.07.059. Epub 2017 Aug 4. PubMed PMID: 28870326. 2: Umukoro S, Adebesin A, Agu G, Omorogbe O, Asehinde SB. Antidepressant-like activity of methyl jasmonate involves modulation of monoaminergic pathways in mice. Adv Med Sci. 2018 Mar;63(1):36-42. doi: 10.1016/j.advms.2017.07.005. Epub 2017 Aug 14. PubMed PMID: 28818747. 3: Inal A, Büyükşekerci M, Ulusoy HB. Antinociceptive Effect of Mirtazapine in Rats with Diabetic Neuropathy. Noro Psikiyatr Ars. 2016 Mar;53(1):12-16. doi: 10.5152/npa.2015.8791. Epub 2016 Mar 1. PubMed PMID: 28360759; PubMed Central PMCID: PMC5353230. 4: Sasaki-Hamada S, Suzuki A, Ueda Y, Matsumoto K, Oka JI. Serotonergic and dopaminergic systems are implicated in antidepressant-like effects of chotosan, a Kampo formula, in mice. J Pharmacol Sci. 2017 Feb;133(2):110-113. doi: 10.1016/j.jphs.2017.01.002. Epub 2017 Jan 26. PubMed PMID: 28233634. 5: Odoma S, Umar Zezi A, Mohammed Danjuma N, Ahmed A, Garba Magaji M. Elucidation of the possible mechanism of analgesic actions of butanol leaf fraction of Olax subscorpioidea Oliv. J Ethnopharmacol. 2017 Mar 6;199:323-327. doi: 10.1016/j.jep.2016.12.052. Epub 2017 Feb 4. PubMed PMID: 28167291. 6: Onasanwo SA, Faborode SO, Ilenre KO. Antidepressant-like Potentials of Buchholzia Coriacea Seed Extract: Involvement of Monoaminergic and Cholinergic Systems, and Neuronal Density in the Hippocampus of Adult Mice. Niger J Physiol Sci. 2016 Aug 30;31(1):93-9. PubMed PMID: 27574770. 7: Ishola IO, Awodele O, Eluogu CO. Potentials of Mangifera indica in the treatment of depressive-anxiety disorders: possible mechanisms of action. J Complement Integr Med. 2016 Sep 1;13(3):275-287. doi: 10.1515/jcim-2015-0047. PubMed PMID: 27276531. 8: Yeom HD, Lee JH. Regulation of Human Kv1.4 Channel Activity by the Antidepressant Metergoline. Biol Pharm Bull. 2016;39(6):1069-72. doi: 10.1248/bpb.b16-00069. PubMed PMID: 27251511. 9: Kishikawa T, Otsuka M, Ohno M, Yoshikawa T, Sato M, Koike K. Development of a screening method to identify regulators of MICA shedding. Biochem Biophys Res Commun. 2015 Oct 2;465(4):764-8. doi: 10.1016/j.bbrc.2015.08.081. Epub 2015 Aug 20. PubMed PMID: 26299929. 10: Lenain P, De Saeger S, Mattiasson B, Hedström M. Affinity sensor based on immobilized molecular imprinted synthetic recognition elements. Biosens Bioelectron. 2015 Jul 15;69:34-9. doi: 10.1016/j.bios.2015.02.016. Epub 2015 Feb 11. PubMed PMID: 25703726. 11: Hamidi-Asl E, Daems D, De Wael K, Van Camp G, Nagels LJ. Concentration-related response potentiometric titrations to study the interaction of small molecules with large biomolecules. Anal Chem. 2014 Dec 16;86(24):12243-9. doi: 10.1021/ac503385x. Epub 2014 Nov 25. PubMed PMID: 25390494. 12: Rouine J, Kelly ME, Jennings-Murphy C, Duffy P, Gorman I, Gormley S, Kerskens CM, Harkin A. Investigation of the mechanisms mediating MDMA "Ecstasy"-induced increases in cerebro-cortical perfusion determined by btASL MRI. Psychopharmacology (Berl). 2015 May;232(9):1501-13. doi: 10.1007/s00213-014-3790-0. Epub 2014 Nov 1. PubMed PMID: 25366875. 13: Prosser RA, Stowie A, Amicarelli M, Nackenoff AG, Blakely RD, Glass JD. Cocaine modulates mammalian circadian clock timing by decreasing serotonin transport in the SCN. Neuroscience. 2014 Sep 5;275:184-93. doi: 10.1016/j.neuroscience.2014.06.012. Epub 2014 Jun 17. PubMed PMID: 24950119; PubMed Central PMCID: PMC4122660. 14: Lee JH, Liu J, Shin M, Hong M, Nah SY, Bae H. Metergoline inhibits the neuronal Nav1.2 voltage-dependent Na(+) channels expressed in Xenopus oocytes. Acta Pharmacol Sin. 2014 Jul;35(7):862-8. doi: 10.1038/aps.2014.30. Epub 2014 Jun 9. PubMed PMID: 24909513; PubMed Central PMCID: PMC4088281. 15: Ishola IO, Olayemi SO, Yemitan OK, Umeh EA. Antidepressant and anxiolytic effects of the methanol root extract of Capparis thonningii: involvement of monoaminergic, cholinergic and GABAergic systems. Drug Res (Stuttg). 2015 Apr;65(4):205-13. doi: 10.1055/s-0034-1376963. Epub 2014 Jun 2. PubMed PMID: 24886981. 16: Nakamura T, Ikeda T, Takeda R, Igawa K, Naono-Nakayama R, Sakoda S, Nishimori T, Ishida Y. The role of spinal serotonin receptor and alpha adrenoceptor on the antiallodynic effects induced by intrathecal milnacipran in chronic constriction injury rats. Eur J Pharmacol. 2014 Sep 5;738:57-65. doi: 10.1016/j.ejphar.2014.05.022. Epub 2014 May 27. PubMed PMID: 24876059. 17: Lin P, Wang C, Xu B, Gao S, Guo J, Zhao X, Huang H, Zhang J, Chen X, Wang Q, Zhou W. The VGF-derived peptide TLQP62 produces antidepressant-like effects in mice via the BDNF/TrkB/CREB signaling pathway. Pharmacol Biochem Behav. 2014 May;120:140-8. doi: 10.1016/j.pbb.2014.03.003. Epub 2014 Mar 11. PubMed PMID: 24631486. 18: Agbaje EO, Ishola IO, Oniyire JA. Antidepressant, anxiolytic, and anticataleptic effects of aqueous leaf extract of Antiaris toxicaria Lesch. (Moraceae) in mice: possible mechanisms of actions. J Basic Clin Physiol Pharmacol. 2014 Feb 27. pii: /j/jbcpp-ahead-of-print/jbcpp-2013-0054/jbcpp-2013-0054.xml. doi: 10.1515/jbcpp-2013-0054. [Epub ahead of print] PubMed PMID: 24572985. 19: Ishola IO, Akinyede AA, Sholarin AM. Antidepressant and anxiolytic properties of the methanolic extract of Momordica charantia Linn (Cucurbitaceae) and its mechanism of action. Drug Res (Stuttg). 2014 Jul;64(7):368-76. doi: 10.1055/s-0033-1358712. Epub 2013 Nov 13. PubMed PMID: 24227474. 20: Daems D, Van Camp G, Fernandez M, Guisez Y, Prinsen E, Nagels LJ. Use of potentiometric detection in (ultra) high performance liquid chromatography and modelling with adsorption/desorption binding kinetics. Anal Chim Acta. 2013 May 13;777:25-31. doi: 10.1016/j.aca.2013.03.031. Epub 2013 Mar 21. PubMed PMID: 23622961.