Ergokryptine
Basic information
- CAS
511-09-1- Standard SMILES
CC(C)CC1C(=O)N2CCCC2C2(O)OC(NC(=O)C3C=C4c5cccc6[nH]cc(c56)CC4N(C)C3)(C(C)C)C(=O)N12- InChIKey
YDOTUXAWKBPQJW-UHFFFAOYSA-N- Molecular formula
- C32H41N5O5
- Average molar mass
- 575.7 g/mol
- Monoisotopic mass
- 575.31076943
Overview
Ergokryptine has been reported in Claviceps grohii and Claviceps purpurea with data available.
Names & identifiers
- Preferred name
- Ergokryptine
- IUPAC
- N-[2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
- English name
- α-Ergocryptine
- Molecular formula
- C32H41N5O5
- Molecular weight
- 575.7
Names & synonyms
ErgokryptineN-(2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo(7.3.0.02,6)dodecan-4-yl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo(4,3-fg)quinoline-9-carboxamideN-[2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamideRefChem:200806.alpha.-Ergocryptine.alpha.-ErgokryptineBromocriptine EP Impurity BC32H41N5O5ergocriptineWLN: T C6656 1A P GN LM CUTT&&J G1 EVM- DT B565 CO EVN HVNTJ BQ DY1&1 G1Y1&1Ergotaman-3',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'.alpha.)-SCHEMBL28072302
Show more names
ergocryptineALPHA-ERGOCRYPTINEErgocrypyineA-ergocryptineα-Ergocryptinealpha-ergokryptine9,10-Dihydro-&beta
SCHEMBL29376491YDOTUXAWKBPQJW-UHFFFAOYSA-NErgotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'.alpha.)-MFCD26143009NSC169479NSC407319SMP2_000196L000687
Database identifiers
- CAS
511-09-1- PubChem CID
- 99049
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 118 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 5
- Heavy atoms
- 42
- Formal charge
- 0
- Complexity
- 1,190
Experimental & physicochemical properties
Collision Cross Section236.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 152 · 152-154°C
- alpha
- 20 · D20 -120° (pyridine); -198° (chloroform)
- Boiling point
- 636.59 °C · 636.59°C (rough estimate)
- Density
- 1.1762 · 1.1762 (rough estimate)
- refractive index
- 1.75 · 1.7500 (estimate)
- storage temp.
- 20 °C · −20°C
- solubility
- 45 % · 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.3 mg/mL
- form
- Solid
- pka
- 9.61 · 9.61±0.60(Predicted)
- color
- Pale Yellow to Pale Beige
- Stability
- Hygroscopic
- InChIKey
- YDOTUXAWKBPQJW-YBALXUQENA-N
- SMILES
- [C@@]12(O)O[C@@](C(C)C)(NC(=O)[C@H]3CN(C4CC5=CNC6=CC=CC(=C56)C4=C3)C)C(=O)N1[C@@H](CC(C)C)C(=O)N1CCCC21 |&1:0,3,10,30,r|
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6 WFB60157B · 6WFB60157B
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 332 · H332-H361-H312-H302-H362
- Precautionary statements
- 261 · P261-P271-P304+P340-P312-P264-P270-P301+P312-P330-P501-P201-P260-P263-P264-P270-P308+P313-P201-P202-P281-P308+P313-P405-P501-P280-P302+P352-P312-P322-P363-P501
- Hazard Codes
- Xn
- Risk Statements
- 62 · 62
- Safety Statements
- 36 · 36/37
- RIDADR
- 1544 · UN 1544 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 1400000 · KE1400000
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- REACH Registrations
- Active
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- KE1400000
- ridadr
- UN 1544 6.1/PG 3
- risk_code
- 62
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 36/37
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard statements
- H332-H361-H312-H302-H362
- REACH Registrations
- Active
- Precautionary statements
- P261-P271-P304+P340-P312-P264-P270-P301+P312-P330-P501-P201-P260-P263-P264-P270-P308+P313-P201-P202-P281-P308+P313-P405-P501-P280-P302+P352-P312-P322-P363-P501
Chemistry & industry
Applications
Usesα-Ergocryptine is an ergopeptine and one of the ergot alkaloids. An impurity of 2-Bromo α-Ergocryptine Mesylate (B682600).
UsesAn impurity of 2-Bromo α-Ergocriptine Mesylate (B682600).
General DescriptionOne of the biologically most important ergot alkaloids is α-ergocryptine. Its semisynthetic derivative, the so-called bromocryptine, is one of the most widely used drugs in this family (e.g., as a prolactin inhibitor or an anti-Parkinsonian)[2].
Additional notes
DefinitionChEBI: Ergotaman bearing hydroxy, isopropyl, and 2-methylpropyl groups at the 12', 2' and 5' positions, respectively, and oxo groups at positions 3', 6', and 18. It is a natural ergot alkaloid. Ergocryptine discussed in the literature prior to 1967, when b ta-ergocryptine was separated from alpha-ergocryptine, is now referred to as alpha-ergocryptine.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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