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MedKoo Cat#: 573483 | Name: Agroclavine

Description:

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

Agroclavine is a clavine type of ergot alkaloid with D1 dopamine and a-adrenoceptor agonistic properties.

Chemical Structure

Agroclavine
Agroclavine
CAS#548-42-5

Theoretical Analysis

MedKoo Cat#: 573483

Name: Agroclavine

CAS#: 548-42-5

Chemical Formula: C16H18N2

Exact Mass: 238.1470

Molecular Weight: 238.33

Elemental Analysis: C, 80.63; H, 7.61; N, 11.75

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Synonym
AGROCLAVIN, Agroclavine
IUPAC/Chemical Name
8,9-Didehydro-6,8-dimethylergoline
InChi Key
XJOOMMHNYOJWCZ-UKRRQHHQSA-N
InChi Code
1S/C16H18N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8,13,15,17H,7,9H2,1-2H3/t13-,15-/m1/s1
SMILES Code
c12c3c(cccc3[nH]c2)[C@H]2C=C(C[N@@]([C@H]2C1)C)C
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 238.33 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: Wu N, Yao M, Xiao W, Dong T, Ma H, Du X, Wang Y, Yuan Y. Modular Pathway Compartmentalization for Agroclavine Overproduction in Saccharomyces cerevisiae. ACS Synth Biol. 2023 Apr 21;12(4):1133-1145. doi: 10.1021/acssynbio.2c00626. Epub 2023 Mar 29. PMID: 36987837. 2: Yu ZP, An C, Yao Y, Wang CY, Sun Z, Cui C, Liu L, Gao SS. A combined strategy for the overproduction of complex ergot alkaloid agroclavine. Synth Syst Biotechnol. 2022 Aug 20;7(4):1126-1132. doi: 10.1016/j.synbio.2022.08.003. PMID: 36092273; PMCID: PMC9428804. 3: Starec M, Fiserová A, Rosina J, Malek J, Krsiak M. Effect of agroclavine on NK activity in vivo under normal and stress conditions in rats. Physiol Res. 2001;50(5):513-9. PMID: 11702856. 4: Vorobyov V, Medvinskaya N, Deev A, Sengpiel F, Bobkova N, Lunin S. Spatial memory deficits initiated by agroclavine injection or olfactory bulbectomy in rats are characterized by different levels of long-term potentiation expression in the hippocampus. Int J Neurosci. 2020 Dec;130(12):1225-1229. doi: 10.1080/00207454.2020.1732963. Epub 2020 Feb 28. PMID: 32072845. 5: Hsu JC, Anderson JA. Agroclavine hydroxylase of Claviceps purpurea. Biochim Biophys Acta. 1971;230(3):518-25. doi: 10.1016/0304-4165(71)90182-6. PMID: 4397222. 6: Robinson SL, Panaccione DG. Heterologous expression of lysergic acid and novel ergot alkaloids in Aspergillus fumigatus. Appl Environ Microbiol. 2014 Oct;80(20):6465-72. doi: 10.1128/AEM.02137-14. Epub 2014 Aug 8. PMID: 25107976; PMCID: PMC4178656. 7: Matuschek M, Wallwey C, Xie X, Li SM. New insights into ergot alkaloid biosynthesis in Claviceps purpurea: an agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine. Org Biomol Chem. 2011 Jun 7;9(11):4328-35. doi: 10.1039/c0ob01215g. Epub 2011 Apr 15. PMID: 21494745. 8: Lv J, Wang B, Yuan K, Wang Y, Jia Y. Regioselective Direct C-4 Functionalization of Indole: Total Syntheses of (-)-Agroclavine and (-)-Elymoclavine. Org Lett. 2017 Jul 7;19(13):3664-3667. doi: 10.1021/acs.orglett.7b01681. Epub 2017 Jun 22. PMID: 28641012. 9: Bajwa RS, Anderson JA. Conversion of agroclavine to setoclavine and isosetoclavine in cell-free extracts from Claviceps sp. SD 58 and in a thioglycolate-iron (II) system. J Pharm Sci. 1975 Feb;64(2):343-4. doi: 10.1002/jps.2600640237. PMID: 236378. 10: Padmanabha R, Shu YZ, Cook LS, Veitch JA, Donovan M, Lowe S, Huang S, Pirnik D, Manly SP. 1-Methoxy-agroclavine from Penicillium sp. WC75209, a novel inhibitor of the Lck tyrosine kinase. Bioorg Med Chem Lett. 1998 Mar 17;8(6):569-74. doi: 10.1016/s0960-894x(98)00072-9. PMID: 9871562. 11: Davidson N, Edwardson JA, Schwab DI. Agroclavine antagonizes depression induced by noradrenaline in the cerebral cortex of the rat. Nature. 1969 Sep 13;223(5211):1166-8. doi: 10.1038/2231166a0. PMID: 5810696. 12: Bobkova NV, Medvinskaia NI, Nesterova IV, Arinbasarov MU. Narushenie prostranstvennoĭ pamiati u mysheĭ pod vliianiem agroklavina [Disruption of spatial memory in mice exposed to agroclavine]. Zh Vyssh Nerv Deiat Im I P Pavlova. 2002 Mar-Apr;52(2):183-8. Russian. PMID: 12013654. 13: Vorobyov V, Yurkov I, Belova N, Lednev V. Agroclavine potentiates hippocampal EEG effects of weak combined magnetic field in rats. Brain Res Bull. 2009 Aug 28;80(1-2):1-8. doi: 10.1016/j.brainresbull.2009.06.010. Epub 2009 Jun 25. PMID: 19559766. 14: Lunin SM, Bobkova NV, Arinbasarov MU. Vliianie agroklavina na uslovno- reflektornye reaktsii aktivnogo i passivnogo izbeganiia u mysheĭ [Effect of agroclavine on conditional active and passive avoidance responses in mice]. Eksp Klin Farmakol. 2001 Sep-Oct;64(5):11-3. Russian. PMID: 11764490. 15: Willingale J, Manzarpour A, Mantle PG. Role of the delta 8 double bond of agroclavine in lysergic acid amide biosynthesis by Claviceps purpurea. Experientia. 1985 Aug 15;41(8):1051-2. doi: 10.1007/BF01952138. PMID: 4018228. 16: Chaudhuri S, Bhunia S, Roy A, Das MK, Bisai A. Biomimetic Total Syntheses of Clavine Alkaloids. Org Lett. 2018 Jan 5;20(1):288-291. doi: 10.1021/acs.orglett.7b03683. Epub 2017 Dec 13. PMID: 29235356. 17: Tyler VE Jr, Erge D, Gröger D. Biological conversions of agroclavine and elymoclavine. Planta Med. 1965 Aug;13(3):316-25. PMID: 5826183. 18: Finn CA, Mantle PG. The influence of agroclavine on the preparation of the uterus for implantation in the mouse. J Reprod Fertil. 1969 Dec;20(3):527-9. doi: 10.1530/jrf.0.0200527. PMID: 5358288. 19: Boĭchenko LV, Zelenkova NF, Arinbasarov MU, Reshetilova TA. Optimizatsiia usloviĭ khraneniia i kul'tivirovaniia griba Claviceps sp.--produtsenta érgoalkaloida agroklavina [Optimization of conditions for storage and cultivation of the fungus Claviceps sp.--a producer of the ergot alkaloid agroclavine]. Prikl Biokhim Mikrobiol. 2003 May-Jun;39(3):335-40. Russian. PMID: 12754833. 20: Edwardson JA, Macgregor LA. The effect of progesterone and some other agents on the failure of pregnancy produced by feeding agroclavine, an ergot alkaloid, in the rat. Br J Pharmacol. 1969 Feb;35(2):P367-9. PMID: 5813116; PMCID: PMC1703224.