エルゴクリプチン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/12/05 21:21:35」(JST)
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alpha-Ergocryptine
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Identifiers |
CAS Number |
511-09-1 Y |
PubChem |
CID: 134551 |
IUPHAR/BPS |
271 |
ChemSpider |
118591 N |
ChEMBL |
CHEMBL1403281 N |
Chemical data |
Formula |
C32H41N5O5 |
Molecular mass |
575.698 g/mol |
SMILES
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O=C3N1CCC[C@H]1[C@]2(O)O[C@](C(=O)N2[C@H]3CC(C)C)(NC(=O)[C@@H]7/C=C6/c4cccc5c4c(cn5)C[C@H]6N(C)C7)C(C)C
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InChI
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InChI=1S/C32H41N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,13,15,17-18,20,24-26,33,41H,7,10-12,14,16H2,1-5H3,(H,34,38)/t20-,24-,25+,26+,31-,32+/m1/s1 N
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Key:YDOTUXAWKBPQJW-NSLWYYNWSA-N N
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N (what is this?) (verify) |
Ergocryptine is an ergopeptine and one of the ergot alkaloids. It is isolated from ergot or fermentation broth and it serves as starting material for the production of bromocriptine.[1]
Chemistry
Ergocryptine is a mixture of two very similar compounds, alpha- and beta-ergocryptine.[2] The beta differs from the alpha form only in the position of a single methyl group, which is a consequence of the biosynthesis in which the proteinogenic amino acid leucine is replaced by isoleucine.
See also
References
- ^ Kren V., Cvak L. "Ergot: the genus Claviceps". Amsterdam: Harwood Academic Publishers; 1999. p. 399–401
- ^ Yates, S. G.; Plattner, R. D.; Garner, G. B. (1985). "Detection of ergopeptine alkaloids in endophyte-infected, toxic Ky-31 tall fescue by mass spectrometry/mass spectrometry" (PDF). Journal of Agricultural and Food Chemistry 33 (4): 719. doi:10.1021/jf00064a038.
Ergolines
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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
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Psychedelic
lysergamides |
- 1P-LSD
- AL-LAD
- ALD-52
- BU-LAD
- CYP-LAD
- DAL
- DAM-57
- Ergonovine
- ETH-LAD
- IP-LAD
- LAE-32
- LSD
- LPD-824
- LSM-775
- LSH
- LSD-Pip
- Lysergic Acid 2-Butylamide
- Lysergic Acid 2,4-Dimethylazetidide
- Lysergic Acid 3-Pentylamide
- Methylergonovine
- Methylisopropyllysergamide
- MLD-41
- PARGY-LAD
- PRO-LAD
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Other
ergolines |
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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)
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English Journal
- Rhodococcus erythropolis MTHt3 biotransforms ergopeptines to lysergic acid.
- Thamhesl M1, Apfelthaler E2, Schwartz-Zimmermann HE3, Kunz-Vekiru E4, Krska R5, Kneifel W6, Schatzmayr G7, Moll WD8.
- BMC microbiology.BMC Microbiol.2015 Mar 28;15:73. doi: 10.1186/s12866-015-0407-7.
- BACKGROUND: Ergopeptines are a predominant class of ergot alkaloids produced by tall fescue grass endophyte Neotyphodium coenophialum or cereal pathogen Claviceps purpurea. The vasoconstrictive activity of ergopeptines makes them toxic for mammals, and they can be a problem in animal husbandry.RESUL
- PMID 25887091
- Dietary exposure to ergot alkaloids decreases contractility of bovine mesenteric vasculature.
- Egert AM1, Kim DH, Schrick FN, Harmon DL, Klotz JL.
- Journal of animal science.J Anim Sci.2014 Apr;92(4):1768-79. doi: 10.2527/jas.2013-7141. Epub 2014 Feb 3.
- Ergot alkaloids are hypothesized to cause vasoconstriction in the midgut, and prior exposure may affect the vasoactivity of these compounds. The objectives of this study were to profile vasoactivity of ergot alkaloids in bovine mesenteric artery (MA) and vein (MV) and determine if previous exposure
- PMID 24492572
- Bovine lateral saphenous veins exposed to ergopeptine alkaloids do not relax.
- Pesqueira A1, Harmon DL, Branco AF, Klotz JL.
- Journal of animal science.J Anim Sci.2014 Mar;92(3):1213-8. doi: 10.2527/jas.2013-7142. Epub 2014 Feb 3.
- The ergot alkaloid ergovaline has demonstrated a persistent and sustained contractile response in several different vascular models. It was hypothesized that different alkaloids isolated from tall fescue (Lolium arundinaceum) will contribute to this contractile response differently. The objective wa
- PMID 24492541
Japanese Journal
- Physiological Roles of Prolactin in the Adrenocortical Response to Acute Restraint Stress
- , , , , ,
- Endocrine Journal 54(5), 703-711, 2007
- … Hyperprolactinemia was induced by transplantation of two adult female rat anterior pituitary glands under the kidney capsule for 2 weeks, and hypoprolactinemia was induced by daily subcutaneous injection of 2-Bromo-alpha-Ergocryptine (CB-154) for 2 weeks. …
- NAID 130004443307
- EFFECT OF HYPERPROLACTINEMIA INDUCED BY PITUITARY GRAFTS OR CASTRATION ON PORPHYRIN CONTENT OF THE MOUSE HARDERIAN GLAND
- , , [他],
- Journal of toxicological sciences 26(3), 151-161, 2001-08-07
- … The histology and porphyrin concentrations of Harderian glands and plasma prolactin levels were examined in B6C3F1 mice castrated or isografted with pituitaries in combination with the administration of bromocriptine (2-bromo-a-ergocryptine), a potent suppressor of prolactin. …
- NAID 110001806916
- EFFECT OF HYPERPROLACTINEMIA INDUCED BY NEUROLEPTIC AGENT, TIMIPERONE, ON PORPHYRIN CONTENT OF MOUSE HARDERIAN GLAND
- , ,
- Journal of toxicological sciences 22(3), 219-229, 1997-08-10
- … The histology and porphyrin content of the Harderian gland and the serum prolactin levels were examined in male B6C3F1 mice treated with neuroleptic buty-rophenones (timiperone and haloperidol) and treated concurrently with timiperone and 2-bromo- α -ergocryptine (bromocriptine), a potent suppressor of prolactin. …
- NAID 110001803642
Related Links
- Sigma-Aldrich offers Sigma-E5625, α-Ergocryptine for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Technical Service: Our team of scientists has experience in all areas ...
- Sigma-Aldrich offers Sigma-B2134, 2-Bromo-α-ergocryptine methanesulfonate salt for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Biochem/physiol Actions Agonist at D 2 and D ...
Related Pictures
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★リンクテーブル★
[★]
メシル酸ジヒドロエルゴクリプチン
- 関
- dihydroergocryptine
[★]
ジヒドロエルゴクリプチン
- 関
- dihydroergocryptine mesylate