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6,8-Dimethyl-8,9-didehydroergoline

HCID 287403
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
548-42-5
Standard SMILES
CC1=CC2c3cccc4[nH]cc(c34)CC2N(C)C1
InChIKey
XJOOMMHNYOJWCZ-UHFFFAOYSA-N
Molecular formula
C16H18N2
Average molar mass
238.33 g/mol
Monoisotopic mass
238.14699858

Overview

Agroclavin has been reported in Claviceps purpurea with data available.

Names & identifiers

Preferred name
6,8-Dimethyl-8,9-didehydroergoline
IUPAC
7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline
English name
AGROCLAVINE
Molecular formula
C16H18N2
Molecular weight
238.33

Names & synonyms

DTXSID109701446,8-Dimethyl-8,9-didehydroergolineRefChem:1073629DTXCID80223836AGROCLAVINNSC93132Indolo(4,3-fg)quinoline, 4,6,6a,7,8,10a-hexahydro-7,9-dimethyl-8,8-dimethylergolineCHEMBL19996207,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinolineErgoline,9-didehydro-6,8-dimethyl-BS-1242
Show more names
NSC 93132agoclavineAGROCLAVINE8,9-didehydro-6,8-dimethyl-ergolin8,9-didehydro-6,8-dimethylergolineERGOLINE,8,9-DIDEHYDRO-6,8-DIMETHYL-
FA334866,8-Dimethyl-8,9-didehydroergoline #Indolo[4, 4,6,6a,7,8,10a-hexahydro-7,9-dimethyl-

Database identifiers

CAS
548-42-5
PubChem CID
287403
DTXSID
DTXSID10970144
ChEMBL
CHEMBL1999620

Properties

Computed structural properties

XLogP
2.6
Topological polar surface area
19 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
18
Formal charge
0
Complexity
375

Physicochemical properties

Melting point
198 · 198-208℃ (decomposition) (ethyl ether )
alpha
20 · D20 -155° (c = 0.9 in chloroform); D20 -182° (c = 0.5 in pyridine)
Boiling point
370.93 °C · 370.93°C (rough estimate)
Density
0.9597 · 0.9597 (rough estimate)
refractive index
1.5 · 1.5000 (estimate)
storage temp.
Refrigerator, under inert atmosphere
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Solid
pka
17.49 · 17.49±0.40(Predicted)
color
Pale Beige
FDA UNII
8 SW57GO7T · A8SW57GO7T
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H312-H332
Precautionary statements
264 · P264-P270-P301+P312-P330-P501-P280-P302+P352-P312-P322-P363-P501-P261-P271-P304+P340-P312

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Treatment · 1 item

Treatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Temporary sedation (e.g. haloperidol) will be necessary in hallucination and diazepam is used for convulsions. There is no specific antidote. (L1921)

Health EffectsIngestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (A2913)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 item

Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Variables relating to these effects are influenced by the agent, dosage, species, tissue, physiological, and endocrinological state, and experimental conditions. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. (A2914, A2915, A2916)

Signs and Symptoms · 1 item

Convulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (L1920)

Chemistry & industry

Uses & manufacturing

UsesAgroclavine is a naturally occuring alkaloid of the ergoline family. Like other ergoline alkaloids, it occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. (L1918)

Applications

UsesAgroclavine is an ergot alkaloid and a fungal metabolite. It is also an environmental and food contaminant.

Upstream & downstream products

Upstream raw materials

(±)-Isochanoclavine I2-Propenal, 2-methyl-3-[(4R,5R)-1,3,4,5-tetrahydro-4-(methylamino)benz[cd]indol-5-yl]-, (2E)-Indole-3-carboxaldehyde

Suppliers9 total

艾吉析科技(上海)有限公司17717235263 · [email protected]
中梦研(湖北)科技有限公司0717-6300888 18062399888 · [email protected]
Sinco Pharmachem (ShenZhen) R&D Co., Ltd.+86-18603013401 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Hazard Codes
Xn
Risk Statements
20 · 20/21/22
Safety Statements
36 · 36
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

risk_code
20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
36
Hazard statements
H302-H312-H332
Precautionary statements
P264-P270-P301+P312-P330-P501-P280-P302+P352-P312-P322-P363-P501-P261-P271-P304+P340-P312
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]

Additional notes

DefinitionChEBI: An ergot alkaloid that is ergoline which contains a double bond between positions 8 and 9, and which is substituted by methyl groups at positions 6 and 8.