HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

Nicergoline

HCID 34040
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
27848-84-6
Standard SMILES
CO[C@]12C[C@@H](COC(=O)c3cncc(Br)c3)CN(C)[C@@H]1Cc1cn(C)c3cccc2c13
InChIKey
YSEXMKHXIOCEJA-FVFQAYNVSA-N
Molecular formula
C24H26BrN3O3
Average molar mass
484.4 g/mol
Monoisotopic mass
483.11575

Overview

Nicergoline is an organonitrogen heterocyclic compound and an organic heterotetracyclic compound.

Names & identifiers

Preferred name
Nicergoline
IUPAC
[(6aR,9R,10aS)-10a-methoxy-4,7-dimethyl-6a,8,9,10-tetrahydro-6H-indolo[4,3-fg]quinolin-9-yl]methyl 5-bromopyridine-3-carboxylate
English name
Nicergoline
Molecular formula
C24H26BrN3O3
Molecular weight
484.39

Names & synonyms

nicergoline27848-84-6NicotergolineNimergolineSermionergobelNicergolinacergodumduracebrolnicergolentNicergolinumVasospan
Show more names
nicergolin10-Methoxy-1,6-dimethylergoline-8β-methanol 5-bromonicotinatemnefi6714TA 079CS-1354
ErgotopMemoqCirco-MarenDilasenilNilogrinDTXSID704560710-Methoxy-1,6-dimethylergoline-8beta-methanol 5-bromonicotinateJCV8365FWN

Database identifiers

CAS
27848-84-6
PubChem CID
34040
DTXSID
DTXSID7045607
ChEMBL
CHEMBL1372950
ChEBI
CHEBI:31902
UNII
JCV8365FWN
EC Number
248-694-6
Nikkaji
J22.054J

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
56.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
5
Heavy atoms
31
Formal charge
0
Complexity
680

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2 items

3.3

3.63

Solubility1.27e-02 g/L
Physical DescriptionSolid
Collision Cross Section · 2 items

213.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

211.69 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
136 · 136-138°
Boiling point
594.4 · 594.4±50.0 °C(Predicted)
Density
1.3558 · 1.3558 (rough estimate)
refractive index
1.62 · 1.6200 (estimate)
storage temp.
-20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility

Safety & regulation

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

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 78 reports by companies from 6 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationNicergoline: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Nicergoline

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
KE6341000
ridadr
1544
hs_code
29396100
Toxicity
LD50 in male mice, rats (mg/kg): 860, 2800 orally; 46, 43 i.v. (Neumann, Lauschner)
risk_code
22
Signal word
Warning

Chemistry & industry

Pharmacology

ATC Code · 2 items

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1 item

Nicergoline is a potent vasodilator (improves brain blood flow). On the cerebral level it prompts a lowering of vascular resistance, an increase in arterial flow and stimulates the use of oxygen and glucose. Nicergoline also improves blood circulation in the lungs and limbs and has been shown to inhibit blood platelet aggregation.

Mechanism of Action · 1 item

Nicergoline acts by inhibiting the postsynaptic alpha(1)-adrenoceptors on vascular smooth muscle. This inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation. Therefore the mechanism of Nicergoline is to increase vascular circulation in the brain, thereby enhancing the transmission of nerve signals across the nerve fibres, which secrete acetylcholine as a neural transmitter.

MeSH Pharmacological Classification · 3 items

Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.

Drugs used to cause dilation of the blood vessels.

Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms.

Cellular LocationsMembrane

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >100
Applications · 2 items

Related reactions

1 records
New reaction record
HRID 1195073 reaction equation
HRID 1195073As reactantuspto-grants-1989_03

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Practically insoluble in water, freely soluble in methylene chloride, soluble in ethanol (96 per cent).
pka
6.33 · 6.33±0.40(Predicted)
form
Solid
color
White to Off-White
Water Solubility
Soluble in alcohol, chloroform, and acetone. Insoluble in water.
Merck
14 · 14,9496
Major Application
forensics and toxicologypharmaceutical (small molecule)veterinary
InChIKey
YSEXMKHXIOCEJA-AQDCORRGNA-N
SMILES
O([C@]12C[C@@H](COC(C3=CN=CC(Br)=C3)=O)CN(C)[C@]1([H])CC1=CN(C)C3=CC=CC2=C13)C |&1:1,3,18,r|
FDA UNII
8365 FWN · JCV8365FWN
ATC code
4 AE02 · C04AE02
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
301 · P301+P312+P330
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn
Risk Statements
22 · 22
Safety Statements
36 · 36
RIDADR
1544 · 1544
WGK Germany
3 · 3
RTECS
6341000 · KE6341000
HazardClass
6.1 · 6.1(b)
PackingGroup
III
HS Code
29396100 · 29396100
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
Toxicity
50 in · LD50 in male mice, rats (mg/kg): 860, 2800 orally; 46, 43 i.v. (Neumann, Lauschner)
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
36
hazard_class
6.1(b)
Storage Class
11 - Combustible Solids
packing_group
III
Hazard statements
H302
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P301+P312+P330

Usesantipsychotic

UsesNicergoline is a drug used for age-dependent cognitive impairment such as Alzheimers disease and other types of dementia. Nicergoline has shown to protect cultured neurons against β-amyloid toxicity. Nicergoline protects against neuronal cell death induced by activated microglia and astrocytes through the inhibition of inflammatory mediators and the upregulation of neurotrophic factors by glial cells. Nicergoline is a drug used for age-dependent cognitive impairment and it protects cultured neurons against β-amyloid toxicity.

Upstream & downstream products

Upstream raw materials

Lithium Aluminum HydrideHydrochloric acid

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
Hebei shuoxi biotechnology co. LTD+8613081092107
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
重庆康洲智通医药科技有限公司173-08362167 17308362167 · [email protected]
南京望知星医药科技有限公司18569809817 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
博瑞生物医药(苏州)股份有限公司0512-0512-62551764 18013103761 · [email protected]
Cangzhou Wanyou New Material Technology Co.,Ltd18631714998 · [email protected]
深圳市恩赞生物医药有限公司0755-25325458 13602565027 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
医恩医疗系统研发(上海)有限公司021-58958002 18930822973 · [email protected]
贵州迪大科技有限责任公司0851-8475-2296 18096062265 · [email protected]
武汉盈邦医药有限公司+86-13296627870; +86-13971566811 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
武汉鹏胤药业有限公司13163333255 · [email protected]
南京世洲生物科技有限公司13675144456 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
天津奥立非医药技术有限公司18202662021 18522876413 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
澳美生物科技(东莞)有限公司13790132747 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
石家庄通洋进出口有限公司[email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
泰安嘉岳生物化工有限公司15318151873 · [email protected]

Additional notes

DefinitionChEBI: Nicergoline is an organonitrogen heterocyclic compound and an organic heterotetracyclic compound.